Watch our lessons for leaders: The Heartbeat Interview ❤️ with Amir Salihefendić, CEO + Founder of Doist

With over 13 million customers all over the world, Amir talks about his motivations as a leader, and the importance of constant learning. 

He also turns the tables and asks me some questions 🙈 Read on…

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Amir Salihefendić, CEO + Founder of Doist

Claire: Hi everyone. I’m Claire Lew. I’m the CEO of Know Your Team. Today, we have an incredibly special guest on The Heartbeat. We have Amir Salihefendić, who is the CEO and founder of Doist, this amazing company that has over 13 million users and builds products like Todoist and Twist, productivity apps that are used all over the world. I think what’s most fascinating is they’ve been able to have this reach with a 50 person company, completely remote, and bootstrapped from the very beginning. Amir, I know I’m a big fan of your work. You’re a member of The Watercooler, our online community, and have just loved always your perspective about leadership. I’m excited to ask you today this one question here on The Heartbeat.

Amir: Well Claire, it’s amazing to be here. I’m also a huge fan of your work. I need some productivity tips because I’m unsure how you can pull it off like all of these projects and you are just like two people. It’s very, very fascinating and inspiring.

Claire: Oh thank you, thank you. I don’t know, it’s never as glamorous as it looks, for sure. If we’re fooling some people, then my job is done. Amir, this question that I want to ask you about leadership that I’ve been asking all sorts of leaders who I admire is what’s one thing you wish you would have learned earlier as a leader? 

Amir: That’s a very good question.

The thing is, I never actually really aspired to be a leader. It’s kind of like I was forced into that.

Maybe having some kind of aspiration to actually learn it earlier or see the value of it, yeah. I was always a lone wolf. I just like to work alone, and I didn’t really like to work a lot with people. Learning all of these skills has been a challenge yeah. I would definitely say yeah, probably much earlier on, I would have liked to have a mentor or somebody telling me, “This actually is very important for your future.”

Claire: Absolutely. I think there are so many people who can relate to that, so many CEOs and managers who I speak with are like, “Yeah, I just found myself in this role.” For you, Amir, let’s rewind the clock here. What did you see yourself becoming? What is the story behind how you became CEO and founder of this company that has millions of customers and you’ve got employees all over the world? How did that happen by accident?

Amir: Yeah. I think if you listen to a lot of stories, it’s like the similar story line where you just have an idea, and you just are very passionate the idea, and you want to see this happen in the world and create this. Then at some point, you figure out, all the skills that I have are not sufficient to actually implement this. Then you need to go out and find people and convince them to join you. Basically, my journey, I saw multiple projects in the past, and I was always very project-driven.

Initially, I think my biggest success, what I thought about was a spell checker. I grew it actually and sold it off. I was still in my early 20s, maybe even younger than that. That’s that, and creating a spell checker, if you use some library stuff, it’s not really that difficult. Then once you venture into how the project … I merged onto this, which is the task manager Todoist for the last 10 years, the complexity is very, very huge. Especially right now, you have so many platforms. You can’t just pull it off all by yourself.

I got up here, I’m like, “Hey, if I really want to make something impactful, I really need to have a team and a company and more people that actually believe the same things that I do.” That’s what’s my story. I think it’s also much more healthy, because I think it’s a very bad habit right now.

The people who aspire to be leaders of their field – that shouldn’t be your inspiration. You should want to create something and then hire people and become the CEO afterwards.

Claire: Absolutely. In some ways then, maybe not learning all the stuff earlier was maybe a good thing? Rather, what I really appreciate about that sentiment Amir is that you’re saying that your focus isn’t to just tell people what to do, or to assume the name or the title, but to actually want to have an impact and to create the work. That was the path that got you to being a leader. I think there’s quite a few people like you said who’ve followed that story line and that are archetype.

I guess my question to you, to circle back to what you expressed as, “Oh, well I do wish I would have known a little bit about what I was getting into.” What would you say, of all the things, comes first to mind of like, “Had I known that this was part of the role, I wish I would have prepared this better,” or you mentioned, “I wish maybe I would have found a mentor earlier so that I could have talked to them more about X”? What is X?

Amir: As you know, it’s like a very diverse job.

You actually have to be good at almost everything. At least know something about everything because if you don’t, then you’re probably not going to be very good. Your company’s not going to be very good at that aspect.

Right now, we don’t have any sales [department]. It’s from the reflection that I don’t know anything about sales, or anybody in the company knows about sales. So we are really, really bad at it.

I think it’s the same thing and everything as a leader, especially as a founder. I think you need to be very good at learning stuff and changing yourself. I didn’t really know that in the beginning. I told you, you just had to cooperate to get products and hire good people…

Claire: That’s not it? That’s hard enough by the way. That’s hard enough as is. You just talked about two extremely difficult things, create a kick-ass product and hire kick-ass people. Those are hard in itself. You’re saying there’s another layer of optimizing and evolving your ability to learn very quickly as a leader it sounds like,

Amir: Yeah. Especially right now, as you’re scaling and adding more people, I think it becomes much more challenging, yeah. Definitely I think I still need to change myself and adapt myself to new situation. Then also people inside the company, we have a lot of people that have been with the company for over five years. They also need to do that. Kind of a journey, as you probably know.

Claire: It’s a journey for all of us. I’m curious, and you slightly touched on this, but I would love to dig deeper into first of all, how do you know what are the things that you’re supposed to be learning? The ocean is infinite and your time is not. Is it that there’s like a pain in the business and you’re reacting to the pain? Is it that you as Amir, you take time off to go out into the woods and you read and you self-reflect? Is it that yeah, you have a small council of mentors that you talk to? How do you know what to go deep on, what to start learning, what to start evolving yourself as you said?

Amir: That’s a very good question. I think there’s different resources you can use. I think Twitter is actually amazingly good. You can filter your feed, and you follow the interesting people. There’s a lot of good stuff there. Even also being part of the community like the Watercooler is also great. Yeah, for instance, book recommendations or an issue that you have, you can go in and see what do other people think you need to do in that situation? I mean even a community I think is very important, even for myself. 

I was an early part of the HackerNews community, though HackerNews is quite toxic right now, but in the beginning it was actually very good and an amazing resource. Over the years it has become worse. The thing is, having a community I think is also very important. Then also just being a sponge. I read a lot, like both articles and books and audio books, podcasts. I doubt you can actually say you need to be very good at a specific thing because you need to know a bit about everything, I think. Then once you have a problem, then you go deeply into it and figure out what should we do here? Yeah, that’s at least my strategy.

Claire: Absolutely. No, I find it actually quite inspiring. I think the undercurrent of what you are describing is two things. One is almost a insatiable curiosity to know more, to be better, to feel like, “You know what? I don’t have all the answers. There are things and aspects that I need to learn.” Then I think also is the refusal to be complacent. I think as leaders, it can be very easy, especially when at least what I’ve observed is usually become a leader be you’re good at something. Rarely do you just get into the position because you’re bad at a bunch of things. You get into the position because you’re good at something. 

When you’re good at something, it’s very easy to really sit on that and be like, “Oh, I’m good at building really good products,” or, hiring people where I can delegate tasks or whatever. You forget the stuff you’re not good at, which was what you’re saying, to really zoom in on. I those are really wonderful takeaways. I’m curious as well, Amir, for folks who are watching this, who are new managers, or who are maybe just really struggling as a founder or as an entrepreneur. How can they put this into practice with limited time? Is there something that you do or say to yourself to remind yourself to be learning, to be reinventing yourself, to be evolving in a certain way? What advice would you have to any new manager or to any entrepreneur who’s struggling?

Amir: Yeah, I would probably have a bunch of stuff to say.

I think the most important part, at least for me, is having a mission and then being driven by this mission. It forces you just to learn and adapt and want to improve.

I do like if you are motivated by something else, let’s say money or fame or whatever else, then I doubt you will actually want it that much. Maybe you will become complacent. Maybe you’ll be satisfied. 

At least what I have found out with me, I am actually never satisfied. I find it very, very brief, because I think it’s an amazing human trait. Then that is really a big energy driver. I can always see what are we actually bad at. Of course, you can’t really become too pessimistic. I think complacency is definitely a huge problem, especially if you have any kind of success. I think it’s very easy to just go and be happy with yourself, yeah. 

Claire: Absolutely. No, I think that advice is gold.

Amir: I’m also very curious. I also have a question for you.

Claire: Oh my gosh. Yeah, let’s do it. I’m all ears.

Amir: You have probably been asked this many times, but I’d actually love to hear your scaling or non-scaling strategy. Why haven’t you hired more? Do you actually plan in the new year to hire somebody else?

Claire: I love it Amir. You’re asking me questions on my own show. Growth is an interesting thing. There’s growth by head count, there’s growth by impact. For me, the thing that I’ve always been interested in is how can we help as many people as possible with being as simple and straightforward as an organization as possible. That’s the first thing that I’ve always thought about. Then the second thing that I’ve always thought about is I’ve always tried to be very honest with myself about what I actually like to do.

It’s funny, because as a profession, I think on leadership, study leadership, talk to leaders 24/7. I don’t really like leading tons of people, if that makes sense. The idea of running a 100 person, 300 person, 1,000 person company, maybe I could do it, but it really wouldn’t be that fun. I think about that a lot, and I try to be very honest with myself of, “Ooh, it’s tempting to hire more people, but Claire, is that actually what you want to focus on doing?” That’s the second thing I think about.

Then I think the third thing that influences me strongly is because I have this and am in this amazing position where I get to talk to CEOs of companies of all sizes, and get to almost peek inside their day. I have a pretty good sense of what I would like in my day to day. I talk to the CEOs that run billion dollar companies that have thousands of people, and I talk to entrepreneurs who bootstrap their company, and it’s 100 people, the whole range. Trying to understand like, what would I really enjoy?

I think what it all comes down to, if you mix all those influences, is again, just really being, you talk about motivation, wanting to have impact with reducing the complexity of the business itself. Here’s the issue that comes with that, is there are definitely constraints. It means that, oh my gosh, Daniel and I, my CTO, there’s so much that we wish we could do and that we’re not doing, or that we don’t feel like we’re moving fast enough and that we’re not. In the past year, what we noticed was, and folks who had been following along, know this as well, is that we noticed a change in our audience as well, and this mismatch with our audience and our product.

After figuring that out, and now looking to the new year, figuring out, “Oh, well I think we now have this really …” I think we’re really finally nailing what we want to offer people and who is actually now listening to us. Maybe it will make sense to hire more people. We’ll see. I always keep my options open for, “Oh, does that mean raise more money?” or raising any money, because we haven’t ever. Does that mean taking out a bank loan? What does that exactly mean? I’m not 100% sure. It’s still actually a little bit early for us to say.

Hopefully that peels back the curtain a little bit, Amir, on my thinking. I think the long story short, because that was very ramble-y, is I have the luxury to peek ahead into all these CEOs who are running companies many steps ahead of mine and just really being honest with myself of, “What kind of company do I want to build? What’s actually fun for me and what’s motivating for me?”

Amir: That makes so much sense. The thing is, there’s a saying, more people more problems.

Claire: Totally.

Amir: Yeah.

Claire: It’s interesting. When I do talk to founders Amir, sometimes I express, “Oh, you know, I do wish we were moving faster on some of this stuff,” and blah blah blah. I remember, I was sitting down with one founder who was like, “Claire, you are two people. You are profitable. You have happy customers. Your product’s awesome. It’s kind of as good as it gets. The minute you start getting any bigger than you are, it just isn’t as fun. It gets more complicated. Right where you are is actually the most fun I ever had running my business. I think if you talk to a lot of founders, it’s the really fun time.” I was like, “Oh!” That’s helpful to hear from someone who’s been through it before.

Amir: Yeah. I think definitely adding people, and this like obsession with head count, if somebody asks you how big is your company, it’s like head count. We can be 1000 people, but maybe it can have no impact or very little impact, and you can be maybe five people and have an amazing impact. I think there’s a vanity metric there, that we need to remove and just focus on impact, but I’m actually unsure how we should measure impact. That’s the problem.

Claire: Totally. I know, and it’s completely subjective. I think for me, my self-check, Amir, is always like, do I want to do this, this idea of growing the business, whatever that means in terms of headcount and impact? Do I want to do it because it makes me feel good to post about it on Twitter and it makes me feel good to tell my friends who are also running companies. “Oh yeah, we hired this person,” or, “Oh, our blog got viewed by this many people,” or, “Oh, this is our revenue.” 

All these, like you said, a lot of vanity metrics, when really for me, what’s most interesting is that I’m making a tangible difference in someone’s actual day to day. How that’s quantified in terms of a number, kind of hard. The most rewarding things are, and I’m sure it’s the same for you, when I get an email from someone who says, “Claire, the leadership training that you gave was hands down the best leadership training I’ve ever had,” or, “This product, Know Your Team, helped me learn something I had no idea about and we saved someone from leaving the company because of it.” 

It’s those, “This blog post Claire, all this totally changed my leadership philosophy.” I just think those are the moments for me where I’m like, “Ah, we have to replicate that,” more than is it exciting to say, “Oh, we hit certain revenue numbers,” which was always great. I’m a fan of money, no worries there, or hiring people. Always you had, for me at least, a self-check of, “Why?”

Amir: Yeah. I think also something that are very problematic. It’s like as you scale and add people, you get these inflection points where things just break, because the complexity becomes too big. Then you need to resolve that, and we have been through multiple of these, and they are very problematic and very energy consuming. I think it’s also, if you can actually stay relatively small.

The thing is, small teams, of instance, Apple’s industrial design team I think, they are on to 20 people, and they have various products and they have changed the world.

Claire: Right.

Amir: I don’t think they would be more productive or more impactful if they had 1000 people working there. That’s also something that we think a lot about. It’s finding the right combination of people, I mean the right people, instead of just adding a lot of them.

Claire: Absolutely. Well then on that note, I have one last question for you Amir, because I can sit here and talk to you for hours about this. On this note about finding the right people, I think one of the most common questions that I get and that a lot of founders discuss amongst themselves is hiring. I know we could probably go really deep on this also and have a whole separate podcast session on just hiring, but you’ve brought it a few times too, it’s importance as the company grows. For you, if you could sum up how you think about hiring the best people, what you look for, what advice would you share for folks who are watching this, about, “Okay, so you have to hire someone. Here’s some things to think about that most people don’t tell you.”

Amir: Yeah. That can tell you what, for me, is a very, very important thing. I think it’s personal projects or the day they actually created something themselves. We have a very, very huge correlation between people that have really been good at their job and have created something themselves.

I think if I look somebody’s resume, and they have only worked for other companies and there’s zero initiative on starting something themselves, so having a side project, something like that, then that’s a huge red flag for me. For me personally, I think that shows that that person is really passionate about something. 

A lot of times, for instance, they can maybe have an open source project they work on during the weekend through the night or whatever. That shows you they do enjoy the work so much that they would work for free and do your spot of like a community at work. Before I founded all this, even right now, I have open source projects that I do on the side, because I actually love to develop. For me, this passion for the job is very, very important. Same with these designers, and even migrating people. For instance, if they are really good at marketing they’re already hang out on ProductHunt and be part of that community there, or something like that.

Claire: Right, have a blog on the side.

Amir: Yeah, exactly. Of course, you can still go out. We have eyes on people that have been amazing and they just didn’t have any personal projects.

Claire: Sure.

Amir: It’s like, you can have a dark horse, but there’s just this huge correlation. Whenever I see somebody that has done something themselves, it’s just like yeah, I feel good about this person. Yeah.

Claire: Totally. I think to your point, it hints at the deeper motivation for why people do it, right? It’s not because I’m getting paid to, but maybe because I actually enjoy it or increases my learning. I think that is invaluable advice Amir. Thank you so much for all of your insights. I learned so much. I actually also enjoyed getting asked questions, finally. That’s actually a really nice change. I know everyone who’s watching this really appreciates all your wisdom as well. Thank you.

Amir: Thank you Claire. Best of luck also with the new product and rebranding. I’m actually unsure how you can do all of that with two persons, again. We need to do a session about personal productivity. I’ll say, write a post about it. I would love to read that part actually.

Claire: I’ll think about it, yeah. I appreciate the suggestion. No, it’s good to know people are interested. Thank you so much again Amir, talk to you soon.

Amir: Bye-bye Claire.

Enjoy this interview with Amir? Check out all our Heartbeat interviews with leaders…

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Peldi Guilizzoni, Founder + CEO of…

As the founder of a 10-year old $6.3+MM bootstrapped company, Peldi talk about how your greatest strength can be your greatest weakness as a leader.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Peldi Guilizzoni, Founder + CEO of Balsamiq. Watch & read what he has to say here…

Claire: Hi, everyone. I’m Claire Lew and I’m the CEO of Know Your Company. I am just thrilled today to have with me the one and only Peldi who is the CEO of Balsamiq, everyone’s favorite prototyping tool. Peldi’s built this amazing company over the past — I don’t know, how many years has it been? We’ve been … Ten, right?

Peldi: Ten.

Claire: I was about to say, I wanted to say 10. It’s been 10 years and I’ve been such a big fan of your work, big admirer of your whole ethos in thinking about building a company. I remember watching your talk a few years ago at Business of Software in Boston. I think that’s where we first originally met. It’s been fun to get to know you, to hang out, to learn from you. Thank you so much for being here today.

Peldi: Thank you. Excuse me. Thank you, Claire. I’m all nervous because you are one of the entrepreneurs that I admire and I follow. I think you are the entrepreneur that has had the most impact on my life for the last year.

Claire: Wow.

Peldi: I’ve basically been reading everything that you ever wrote.

Claire: That just makes my day. I will take that. All is good in life if I can get that from you, Peldi. Thank you so much. One other thing, too, I want to mention to everyone who’s watching The Heartbeat, you’d mentioned to me that you actually also, aside from reaching the 10-year anniversary of Balsamiq, you guys recently launched a web app as well, which is really exciting. Those watching should definitely check that out. Peldi, here’s the thing, I’m here to extract wisdom from you today. I want to ask you this one question that I’ve been asking leaders I really respect and admire, and that question is:

What’s something you wish you would’ve learned earlier as a leader?

Peldi: Lots of stuff for sure, but there’s one thing that I came across that sort of was a light bulb moment. A few months ago, I was reading some of your guides on how to give feedback, and give and receive and all that. I came across this little video by Leo Widrich who was one of the co-founders of Buffer, and he was talking about some feedback that he had received from Joel of Buffer, which really opened my eyes.

The idea is that sometimes doing what you’re really, really good at actually hurts the company, which is very counterintuitive. Let me explain.

Claire: Yes, please do.

Peldi: In my case, I see it all the time. I’m really good at getting stuff done. I start projects, work on them, communicate with the right people, I make it happen. I do project after project after project after project, and I’m thinking I’m killing it. Then you realize that as a CEO, 10 years into it, I shouldn’t be doing any projects. I should have delegated everything by now. Now the team continues to rely on me to get stuff done instead of learning how to do it themselves. If I ever decide to go on vacation or burn out, then I leave them hanging.

Another example is my whole goal with Balsamiq is to learn as much as I can forever, be challenged and learn. I’m really good at that. If there’s a challenge, I dive in, I do the research, I know how to do research quickly with enough information to solve the problem. I’m learning, I’m learning, I’m learning, I’m learning, and I’m applying, but I’m never teaching what I learn.

Claire: Fascinating, yeah.

Peldi: I become good at all these thousands of different things including GDPR for instance.

Claire: Yeah, you and me both.

Peldi: Yeah, I mean in the last few months, I’ve done a lot of research on GDPR, another research on how to create a culture of feedback, completely unrelated, but things that our company needed. But instead, I should be teaching others how to do research.

Basically, you think you’re doing great, but you should take a step back and think okay, strategically, am I helping the company? Imagine the company without you in 50 years. Are they going to be ready to go?

Claire: Totally.


What I realized is that I should stop myself from doing things I’m good at — which is so counterintuitive — and instead, focus on delegating training and making sure that everybody gets good at doing those things.

Claire: Absolutely. It’s this idea that … I mean there’s so many layers here, Peldi, that I want to sort of peel away at because you talk about essentially saying that you being good at something isn’t enough in a company. It’s not that you just can’t be good at it. It’s other people have to be good at it or else the organization doesn’t become self-sustaining. I think that’s a like you said, it’s a very counterintuitive nuance as a leader to understand that it’s not about me being good at these things. It’s about other people. I think that’s one fascinating takeaway-

Peldi: Yeah, and it’s tricky ’cause no one’s going to stop you because you are doing a bunch of stuff. In Leo’s case, he was lucky he had a co-founder in Joel and Joel realized that this was happening and he told him. I am a solo founder. The employees, no one-

Claire: No one tells you, yeah.

Peldi: It’s not their job. They’re like all right, you’re doing great.

Claire: Yeah. I was going to ask you, that was my next question, what caused you to recognize this realization? Did you have like a wake-up moment? Did someone say something? Was it something you read ?

Peldi: It was this little video that I came across while I was doing research on feedback and it was just timely. If I saw that video five years ago, I would’ve said it doesn’t apply to me, whatever. Now 10 years into it, I’m maturing more, I’m finally maturing as a CEO and so, I’m more receptive to that kind of a feedback-

Claire: Absolutely. Question for you then, why do you think, and for folks who are watching I will be sure to share that, that video that Peldi’s alluding to, why would the five years ago version of Peldi have disregarded that video? What is it that’s been different? What are you more open to or more sensitive or self-aware about? What’s changed?

Peldi: What’s changed is that we’re 10 years old now. That was sort of my big old goal from the beginning. I wanted to build a long lasting company and 10 years is pretty impressive for a software company. Now, I’m thinking about the next decade. In the next decade, my new goal is to make sure that I help Balsamiq become stronger than me and able to not only outlast me, but also outgrow me.

Claire: Absolutely. It sounds then like being able to resist seeing your strengths as sort of the only way you can make an impact on the business, it’s the only way actually for the company to grow and to outlast you as the founder, then the organization isn’t just you as the CEO. It’s not just about Peldi. It’s now Balsamiq. It’s something bigger.

The other thing I was curious to get your take on, Peldi, is I was thinking about why it’s actually so difficult for founders to not play into their strengths? For you, you’re good at getting stuff done. You’re good at picking up and learning new things. I was thinking for myself like, “Oh, what are the things that I’m good at?” I think someone might say that, “Claire, you’re good at communicating things, you’re good at writing,” and yet I would argue just like to your point that sometimes, I probably over-communicate things. Even within our tiny, tiny company, I probably over communicate stuff. I’m pretty sure if I were to look back, I’d go I didn’t … It’s good to communicate, but maybe ’cause we’re so small, maybe it’s too much.

Peldi: Yeah, too much, yeah.

Claire: I was thinking about it and I’m curious to get your take on it. I wonder if it’s because we like doing things that we’re good at.

Peldi: Yeah, I think there’s two things, maybe three.

One is definitely there’s a lot of ego that goes into being a founder.

You’re proving to yourself that you can do this over and over. You like the challenge and you like to overcome the challenges. Diving into tough projects is fantastic. It’s another chance to prove to yourself, yes, I’ve overcome this obstacle as well.

The second thing is after a while — and it’s related — it’s doing things you’re good at becomes something that makes you feel good. ’Cause if you were to focus on the things you need to work on all day, you feel completely inadequate. You don’t know what you’re doing. Sneaking in a project here and there or doing an extra piece of communicating, something that you know is going to work helps you feel better I think. There’s a little bit of a laziness, but also sort of mental health, you need a little bit of a pick-me-up once in a while. Doing what you’re good at is good. Yeah, which is why I guess what you said we like doing that stuff.

The third is that it could be completely a blind spot. You don’t even realize you’re doing it. It’s just a habit. It’s just how you operate, and no one’s stopping you, and you never notice unless you watch this video.

Claire: I was just about to ask you. I mean that was literally my next thing. I was like it almost sounds like if it’s sometimes the things that we’re good at that we like and that makes us feel good that are actually hurting our company, how do we ever find out what these things are, Peldi, other than like you said, stumbling on this video on YouTube?

Peldi: The way Leo did it was having a co-founder or I guess you could have advisers, but they don’t work with you day after day all day so they might never notice as well. I think over time, if you have an executive team, you have to teach them to do this as well. You have to create a culture of feedback so strong that they will even give you feedback about stuff that you’re good at, not just what you need to work on. But I bet that’s really tough to create and I haven’t been able to do it so far, but I’m working on it.

Claire: It’s an imperfect process and more art than science I think. I am curious, too, I can only imagine, there are some folks who are watching this, Peldi, who are thinking maybe, maybe some strengths are getting in the way, but there are certain things in my company, Peldi, that I only can do. There are certain things that only I am good at.

Peldi: Absolutely.

Claire: How do we as leaders, how do we make that distinction between these are the things I actually cannot give up and compromise on because Balsamiq would completely just go off the deep end and then, these are things where no, I need to get this off my plate, I need to teach other people how to do this stuff? How do you make that distinction?

Peldi: I think the answer changes depending on where your company is in its lifetime. I think I can only start thinking about these things now because we are stable. We are very profitable from the beginning. We have 30 people now and so, there is a chance that we’re going to stay in business for another few years. It’s pretty likely. So my horizon expands because I have these certainties. Five years ago, if somebody said, “You need to think two years in advance,” I would say, “You’re crazy. I’m drowning. I’m just trying to tread water here.” To people who say that, I say, “Fair enough.” If it’s very likely not applicable to you, but you should keep this in the back of your mind for the future because I feel … I don’t know. Not everybody’s goal in life is to build a long lasting company.

Claire: Sure.

Peldi: But if that’s your goal, then you have to keep this in mind because you’re not going to be around forever. After a while, you get too old. You want to retire or something happens, you want to-

Claire: Yeah, do something else, yeah.


What I wish I would’ve done is ratcheted down my doing and my learning, and increased the teaching to do it gradually ’cause now I’m 10 years in and I’m realizing that the company revolves around me too much still.

And I burned out and I’m like, “You guys, I’m out. See you in a couple of months,” and that’s a disaster ’cause they’re not ready. I haven’t prepared them. But actually, what’s happening is that my team kicks ass and they all stepped up, and they’re teaching me how to do it so it’s awesome.

Claire: Yeah, they saved you. I feel you. I feel you. I think I mean for me personally, Peldi, as a leader, one thing that I’m taking away is to not assume always that our strengths are good for the company, just not to make that correlation so automatic. I love that. That’s something I’m going to be taking away. Two, I think this idea of reflecting on how focusing too much on our strengths can actually strangle the company I think is also a really interesting takeaway. I think regardless of business life span, I’m thinking even that small reflection process whether you take 10 minutes once a year or you survey your employees and you would just ask a couple people like, “Hey, would you like to know how to do this stuff? Would you like to be doing more of this stuff?” Then I love lastly, one thing I really hope people take away is this idea that teach more, do less and maybe the longer your company is in business for, maybe you ramp up the teaching and you lower the doing.

Peldi: Exactly, exactly.

Claire: I think that’s how you scale. I think that’s incredible wisdom.

Peldi: I wish.

Claire: Hey, I’m learning from you. We’re all learning from you, Peldi. Thank you so much for being a part of this. We all appreciate it.

Peldi: Thank you very much, Claire.


P.S.: If you did indeed enjoy this piece, please feel free to share Thanks 😊 (And you can always say hi at @clairejlew.)

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Wayne Sutton, Co-founder + CTO of…

As a serial entrepreneur who has been featured on CNN, USA Today, BBC, and the Wall Street Journal, Wayne talks frankly about self-awareness and depression as a leader in our interview.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Wayne Sutton, Co-founder + CTO of Change Catalyst. Watch & read what he has to say here…

Claire: Hi everyone, I’m Claire, and I’m the CEO of Know Your Company. Today, I am super excited to have with me, Wayne Sutton, who is a serial entrepreneur. He’s also the Co-founder and CTO of Change Catalyst, which hosts Tech Inclusion, this great tech conference. And he’s just in general, extremely passionate about making the tech industry more diverse and more inclusive.

I actually have never met Wayne in person. I actually read this really insightful piece that he wrote on Medium a while back about entrepreneurship, and depression, and self-awareness. It was so vulnerable, and I thought, so well done that I reached out cold and really wanted to have you on The Heartbeat.

So, Wayne, thank you for being here. I’m excited to ask you this one question about leadership.

Wayne: Thanks for having me. Thanks for reaching out, and looking forward to the conversation.

Claire: Absolutely. So, okay, Wayne, here’s the question. It’s what’s one thing you wish you would have learned earlier as a leader?

Wayne : Great question. The one thing I wish I would have learned early as a leader is self-awareness. Self-awareness about how I process my thoughts, my emotions. How and why I feel a certain way in certain interactions, in certain environments, or how did I even become self-aware to identify trigger moments, or trigger interactions with people, and what can I do to positively make change when a trigger moment happens. That could be something from my childhood, or a relationship, or another professional environment.

And also, in self-awareness, I wish I would have learned about how environments affects my productivity. How disruption, in terms of workflow, or meetings, or interactions, can increase or decrease my momentum in terms of being productive throughout the day, and what do I need to do to refuel myself.

So, if I had to sum it up, self-awareness about how to process my thoughts, my emotions, my interactions, that helps me be a better person, a better leader, a better human, and a happier individual.

Claire: Absolutely. I love that answer, Wayne, because I think self-awareness is probably the most underrated aspect of leadership. There’s not a lot of books that you read about self-awareness with leaders. You read about power and authority and decision making and strategy and growth, but not often about self-awareness. So, I love that that’s something you mentioned.

For you, when in your career did you realize how important this was. Was this something sort of very early on when you were starting to become an entrepreneur you realized right away, or was this something kind of later in your career, and only more recently where you realized the importance of self-awareness?

Wayne: It was way more later in my career. It was after when I’d hit rock bottom. like many people, you hit rock bottom.It came in a situation where I literally moved all the way across the country from North Carolina to San Francisco. I had a very young son, I was going through a separation, divorce, I had co founded an incubator and accelerator for underrepresented founders. I made a decision to leave that and now I’m in this whole new world, a lot of sacrifices, different environment. I had a very small support network in the Bay Area, not that many friends. There’s a lot of homelessness here, 90% of the homeless I think is African American, so people look like me, and I went through a stage of deep, dark depression.

I would probably say the middle or after that, I started reading books. Everything on conflict resolution, co-dependance. Books around love, books around meditation. I started getting into meditation, started a meditation practice. At first, 3 minutes, 10 minutes, 20 minutes. Along with that journey, I had to take some time off, and then through all of that, I started going to a therapist, and that therapist started helping me process all those emotions and get to some root cause of my thinking patterns and my mindset that created some a-ha moments for me. It was like, this is why I feel this way. This is why I think this way. And through all those trials, and those interactions, and sessions in therapy, and reading books, it started answering one question. And the question was why?

As I started getting to why, you become more self-aware.

Claire: Yes. First of all, I’m blown away by that level of self reflection because I think for all of us in our lives, we hit a moment of rock bottom. It’s different levels for different people, right? Of course. But there are always turning points in people’s lives, where you go, “Oh yeah, that was a dark time,” or, “Oh, that was not when I was at my best.” And I think it’s interesting the reactions people can have to that. So you can sort of bulldoze your way through it and sort of keep your habits the way you’ve always been doing things, and you just kind of find a way through it, and the path that you’re describing, Wayne, requires a lot more introspection, requires a lot more change, and self reflection.

And you said the most important question is why. I think, I guess for the leaders who are watching this, who may be saying, “Wayne, I’ve been in ut situation. I’ve been through a traumatic low-point in my life,” or, “I’m going through that right now.” What advice do you have for them to have the courage to be this introspective? ’Cause it’s scary. How did you decide to, for example, go see a therapist? How did you decide to start doing some active self work and reading books? How did you decide to start asking this question, why?

Wayne: I wanna say, first, I wouldn’t be here if it wasn’t for my family, close friends, mentors who care about, and people who I may have had one or two interactions with, who are now like my mentors and lifelong friends. So that’s one. And then, after that, the time I took off was the most helpful in that moment.

Claire: Yeah.

Wayne: I understand that I was in a privileged environment to be able to say, “All right, I can take almost a month off and disconnect from everything.” A lot of people can’t do that. But I was able to do that. It’s one of the good and bad problems about hitting rock bottom, you have nowhere to go but up. And so, took that time off, and then once I got emotionally, intellectually back on track, I was reminded of my goals. Reminded that I have a son. Reminded why I came to San Francisco. What were my objectives? What did I want to accomplish in life? And from there, it was like, with baby steps, making little small changes, say, “I can’t give up.”

That’s number one. Number two, is that … Create a plan. I had put things in motion before I took the time off that okay, I was moving into a new apartment in San Francisco, that was gonna be available when I got back, or when I was ready. I had a job offer with a startup, that was gonna be ready when I got back, if I chose. My divorce was final. I had a little bit of cash, I said, you know what, I can do this. And then with that plan, was continue with the therapist. I met with a couple in San Francisco, there’s not a lot of like … Their black population is, I think, 5%, and therapists I think is maybe 1%. I got fortunate to connect with the one black therapist, ’cause I wanted someone who can relate to my culture and identity. She was phenomenal, and to help me understand what was going on.

And so, with all that, that plan, that strategy, it helped me get to a level of action to question like, why? Why did I feel this way? Why did I think there was moment where I had to give up? Why did I make those decisions to even move out here. Like all these things helped me identify the why.

Claire: Yes.

Wayne: I hope I answered your question.

Claire: Oh, beyond. Even beyond what I was originally asking, Wayne. So many threads I wanna pull on here and highlight for people who can relate to this situation. I mean, one, you talked about the importance of a support group and a support network and a community, and I think as leaders, it’s so easy to say that we can go it on our own. That we don’t need anyone, and that we’re the leader, everyone’s looking to us when in reality, something that I love, that you talked about was no, lean on your close friends, lean on even acquaintances who’ve said that one encouraging thing to you. So, I think that’s something that’s really key.

And I think the second sort of piece I want to highlight that you mentioned, is the importance of pausing and taking a break. We rush so easily in our day to day lives, especially as leaders, to find a solution, to work at a certain pace, and that’s great. I’m all about speed and getting things done, I’m sure you are too. No one’s saying not to do that, but you said you took a month off, right? And the importance of pausing. Yeah, I’m curious, Wayne, when you wrote this blog post around self-awareness, and I’m sure as you talked to plenty of entrepreneurs and founders, what advice do you give them around being more self-aware? Is there anything that feel like you wish you would have known earlier in terms of … Or sharing with people, “These are things I wish I would have known earlier,” or, “Make sure to sort of take advantage of these things as leader,” or, “Be mindful of these things.”

Wayne: Yes, it can be challenging working with entrepreneurs who are not ready to process that. And something I wanna touch on before I answer that question, is on a comment you made about taking that time off, and being transparent, because we have made a huge mistake in the tech industry identifying role models with God complexes, type-A behavior to have all the answers. We have made a huge, human, fundamental, cultural mistake in the tech industry, ’cause that’s not how we are as humans. That’s not actually how we do business. That’s not actually how we succeed in life.

And often, you hear these stories of people, and I’m not Richard Branson, or –

Claire: Elon Musk, yeah.

Wayne: I try to use … I try not to use no more than one white male example at a time, ’cause there’s more, right?

Claire: Of course.

Wayne: There’s Rob Johnson, who’s a billion dollar African American investor. So, it’s like, there’s all these people who come out later and just talk about, “Oh,” like when they made it. And so, I just wanna touch on that, that as humans, and we talk about leadership, you don’t have to have all the answers. And I strongly believe, the more you can take time to refuel, reflect on the little wins and the losses, and be transparent about your feelings, the better you will be, and you will be able to lead.

Claire: Yes.

Wayne: So, take your time off. And so, with that, the advice I often give entrepreneurs, because many are just going. That’s how I was early in my career. I’m in my 40s now, and they’re just going. They’re trying to get money, they’re trying to raise money, they’re trying to get their product launched, they’re trying to find a CTO, they’re trying to launch a company, they’re trying to get customers, and they’re just focused on the goals. I’ve been there, you’re so focused on, I need to hit this metric, I need to get this goal, I need to meet this person who’s gonna change my life. And you’re not taking a step back to say, okay, you meet this person, but how are you feeling? What are gonna do? What happens if everybody says yes? What happens if everybody says no? How you gonna deal with that emotionally? How can you handle rejection? How do you handle success? Are you grateful for the little wins? Do you celebrate that gratefulness with your colleagues?

So, you try to break it down into simple transactional interactions that are emotional. And then you start processing that way, then it’s like, oh, I don’t know how … what happens if get told no, I don’t know if I’m told yes, and we get the deal, and everything’s perfect, I don’t know. I’m gonna be happy, yeah. But then what happens if you are told no 100 times and try to raise a million dollars, and you’re like, I’m going to succeed no matter what. Have you thought about how you handle rejection? And those type questions get to a process of becoming self-aware. Because it starts making you cognitively think about how you deal with interactions, and then it also touches on the why, because it’s like you may be angry and taking it out on a coworker, maybe upset because you didn’t reach your big vision of raising a million dollars, but what’s the why with that? You tried so hard and you were told no, no, no, no. Or when you know you deserve a raise, a salary promotion, and you see a coworker or a male get it, and you didn’t ’cause you’re a woman, and you know you deserve it. So that’s your why.

So, try to break it down to transaction interactions is how I interact with entrepreneurs to help them become self-aware, and then once they become … Get to that state where they understand well, this is why I’m not happy or I’m not succeeding, or I’m not in a good emotional state, then we’re talking about solutions.

Claire: Absolutely. I love what you’re saying about just slowing down that process for how we make those decisions instead of rushing into them, and I mean, I’ve caught myself in this often, which is you’re on autopilot. You see the goal, you know what you need to do, and it’s just a matter of sort of sprinting, or running to get there, but you know, that’s how athletes injure themselves, right? It’s when they’re not training properly or sleeping well, or understanding the mechanics of their body, or asking if they’re over stressing a certain part, right? Not to take the analogy too far, but I think turning off that auto pilot and really self reflecting is how we build that self-awareness.

Wayne, thank you so much for your incredible insights. Yeah, it’s just refreshing to have such a clear and real perspective on the psychology of being a leader, or being an entrepreneur, and not always having everything go your way all the time. ’Cause that sure is life, so thank you.

Wayne: You’re welcome, you’re welcome. And you’re right, that’s how life works.

Claire: You got it, thanks again.

Enjoy this interview with Wayne? Check out all our Heartbeat interviews with leaders…

P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Hiten Shah, Founder of KISSmetrics…

As the founder of multiple successful SaaS companies, Hiten shares the pitfalls of being too nice as a leader and the importance of the word “outcome”. (And yes, he is in his car while filming this 😝)

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Hiten Shah, Founder of KISSmetrics, CrazyEgg and now FYI and Product Habits . Watch & read what he has to say here…

Claire: I’m Claire Lew and I’m the CEO of Know Your Company and I am super excited to have with me today Hiten Shah, who many of you I’m sure are familiar of. Hiten is an amazing entrepreneur who’s founded a lot of software company, whether he was the founder of CrazyEgg or KISSmetrics, and is now working on two different startups and products. One is Product Habits and then the other is FYI.

Hiten and I, we met, I think, a few years ago, maybe at a conference. I’ve always been a real big fan of your work and excited to ask you this one question about leadership.

Hiten: Yeah, I think we met at MicroConf, if I’m not mistaken.

Claire: I think you’re right, too. Yep. I think it was a couple of years ago in Vegas.

Hiten: Yeah. I’m excited to answer the question and I don’t know what it is yet.

Claire: And I love, also, that you’re calling from a car. You are the first person I’ve interviewed to be calling from a car. Which you clarified, though, you are not driving.

Hiten: I am happy to take that claim. No, not yet.

Claire: Here’s the question. What’s one thing you wish you would’ve learned earlier as a leader?

Hiten: Oh wow. What’s one thing I wish I would’ve learned earlier….

This question’s interesting because, I think when you ask it, I can have a recency bias and say, “Oh. One thing I’m dealing with now that I wish I had known earlier.” But I don’t think that that would be appropriate. So I’m gonna need a couple seconds to think ’cause it’s a good question.

I’ve been I guess doing this for a really long time, and I think I’m not very good at it, to be honest. So I would say that I’m just looking to get better all the time at being a leader, whatever that means.

I think that the one thing that I feel I wish I would’ve understood and knew previously, much earlier, and I wish someone would’ve told me or even if they did maybe I wouldn’t have listened. But I think the big thing is as a leader, as a person who’s responsible for other people — so that’s what I would call a leader in some capacity, just to give it a definition. In the past, I was so very focused on being a nice person, and I recently, and this is another recency bias but I think this was really important for me.

I shouldn’t be necessarily interested in being a nice person and looking to be nice to everyone that works on the team. And I don’t mean that I would be mean, because you would think that’s the opposite. But I want to be objective. I want to be accurate. I want to be honest. And I think a lot of times, and especially this applies to founders I’ve met, they’re nice people, and that prevents them from being honest. That’s the aspect I’m constantly putting myself in check. Am I just being nice? Or am I actually being honest?

Claire: Yes.

Hiten: And there’s a nice way to be honest. But, I think when we think about honesty and being nice, I don’t think they’re related. I think that they aren’t instantly you’re like, “Oh you could be honest and nice.” I think a lot of people believe that if you’re gonna be direct and you’re gonna be objective and work with people and give them feedback and talk about mistakes and problems and how to get better. It’s hard to be nice and honest at the same time.

Claire: Absolutely, no totally.

Hiten: To be honest about it, and I think there’s a big difference between being nice and being honest. Going forward, one of my goals for myself is to not worry about being nice, but be more focused on being honest first in a nice way.

Claire: When did you realize this, Hiten? So, did you get burned by a situation? Is this a pattern that you sort of accumulated over time? Do you feel like there were some sort of big wake up calls where you were like “Whoa, maybe if I focused more on being honest versus nice, we wouldn’t be in this situation” or “I would’ve let this person go earlier” et cetera, et cetera?

Hiten: I think I’ve made that mistake too many times of not letting somebody go earlier and it’s because I wasn’t willing to be honest with them. Instead, we would, you know, people would have discussions about them when they weren’t in the room. We’re a remote team but it’s still the same analogy. And once that happens more than a couple times — a handful is too much, and it usually happens a lot more – there’s something you need to do, and usually what that means is you need to go talk to that person.

Claire: Yes.

Hiten: And I think that there’s a level of toxic culture that develops when you don’t do that that’s hard to see, especially on a remote team.

Claire: Yes. Yes.

Hiten: So, I spent so much time making people on the team feel like I’m nice, just like I would make somebody who I’m advising or a friend or anybody who’s more of an acquaintance or what have you, and then I should be nice. Yeah, there’s really nothing at stake there in those relationships in that way. And the funny thing for me is I was way more honest with those people than I tended to be with people on my team. Because if you ask around about me, when I give advice to people not on my team, I’m very honest with them because I want to do what’s best for them. I don’t have more than a meeting or two usually and I’m trying be helpful and being honest is the best way to be helpful to them.

While on the team, these are long-term relationships, most of the ones I have- or they should be, or they want to or are going to be if we’ve done our job right in hiring people and having them join the team. And I feel like honesty is way more important in those situations. I don’t want to be perceived as a nice person necessarily — I’d rather be perceived as someone who is very honest and direct and wants to help people get better through that.

Claire: Absolutely.

Hiten: And I personally struggle with it. I’m not sure how that relates to anybody else and their experience necessarily, but your question was a good one.

Claire: Yeah, yeah. Well, to that point, so this is something that has come up a lot in leaders that we talk to and we work with. We run this online leadership community called The Watercooler where we have over almost 1,000 leaders talking and chatting about their different problems and concerns and one of the things that people bring up a lot of the times is, “Claire, I have trouble giving feedback” or “Eeryone knows me as the nice guy, so how do I go from being the nice guy to being the honest person?”

And when I used to do consulting work, prior to running Know Your Company, one of the biggest trends that I would find in organizations and teams was what I called a “culture of nice” and how do you kill a culture of nice? So it’s even when the entire team starts to embody this whole like, “Oh, good job. Smiley face. Pat each other on the back” and then like “Hmm, do we bring up this mistake? How do we talk about things openly if all we do all day is sort of like, smile and nod our heads and agree with each other all the time?”

So to your question of “Are other people facing this?” – absolutely. My question always is, “Why?” So why is it so hard for people, ‘cause I like being nice, trust me. I’m a pretty smiley person, I like to think I’m a kind person. I know what you’re talking about, Hiten.

So why is it so hard for us people who self-identify as “nice people” to realize that maybe that’s not always the most productive path or that it’s possible to be both nice and honest. And I’ll throw something out there just to sort of poke at both of us here, which is: Is it because we want to be liked? Is it because we care a lot about what people think about us and just want to be liked by people we have worked with for a long time? What’s going on here? Versus say, outsiders, like we don’t really care if they like us or not, but like our team, we kind of really want them to like us. Is that it? I don’t know.

Hiten: Well, if people like you, they want to be around you. Sio f people like you, they want to stay in your company.

I think there’s a basic human nature of “I have to deal with this person all the time. It should be a pleasant experience for every time.”

Claire: Yes.

Hiten: Now, you can apply that to your partnership, your life partnership, or if you’re married, your marriage, whatever have you, because yeah, that should be pleasant to each other. I think that’s important. I think it’s important to get through conflict. A lot of people call some of these relationships at work- whether it’s co-founders or other things “marriages” and I’ve come to terms with that it’s not the same. And the reason I think that it’s not the same and the reason I went from nice to more focused on being honest, which takes time to develop, I think, is that in a business, because we’re talking about a business here, there’s outcomes. There’s outcomes, there’s things we’re looking to accomplish. So our basis isn’t “we have a family” or “there’s two of us and we’re partners and like that’s just how it is” — this is outcomes.

There’s a third factor. It’s not just about me and you, or me and the team, or us as a team, if we’re a team there’s outcomes. So if you think about if we’re being nice, we might forget the outcome because we’re just being nice to each other.

Claire: Absolutely

Hiten: So, to me, the outcome changes construct relationship and we tend to treat our relationships at work the same as our personal relationships, if we’re nice people or want to be perceived as nice when, truthfully, we have outcomes we want to reach and every single individual on the team is responsible for things.

If you’re not honest with them about their responsibilities and expectations and things like that, I think you end up in a place where you’re gonna reach those outcomes that you want for the business. Which is good for everyone!

Claire: I completely agree. Amen.

Hiten: So it’s kind of messed up to be nice and not honest and then not get to your outcome, right?

Claire: No, absolutely. I think your point about a lot of folks in start-ups or business or leaders conflating family relationships or personal relationships with business relationships, I’ve always thought that was actually a mess. I hate it when founders talk about how, “Oh, my team is my family!” It’s like, “Really, though? Because the purpose of your family is not to accomplish this goal to create a better outcome in the world or create impact or create revenue or whatever your goals are. Like your family doesn’t have business goals, your team does.” And the whole point of an organization is to actually accomplish something. It’s not actually about just making sure everyone feels good, because if everyone feels good then you’re actually not accomplishing anything.

It’s actually even why I hate the buzzword “employee engagement” ’cause it’s this idea that everyone just needs to be engaged. It’s like, “Yeah, when people feel good about their work then they’re going to do better work.” But are they gonna feel like that all the time? No. And is it- should the focus be on just having people feel good without any concern about if the actual goals are being accomplished? No. And so I think you’re absolutely right. It’s almost this over-reliance on thinking that everyone just needs to feel good and that’s what gonna- and that’s sort of the outcome, when obviously there’s very different outcomes.

So, question for you, then, Hiten. Last thing here before you go. For perspective founders or current founders and leaders who are watching this and who have been nodding their heads going, “Yes, Hiten, I’m with you. I’m the nice gal- or I’m the nice guy- in the organization” and it sounds like you’re working on this- what advice to you have for them? Is there anything you’re sort of consciously thinking about or doing or talking to folks about just to make sure you are more honest than you are nice?

Hiten: I think one of the most powerful tools is the ability to reflect and do the equivalent of a postmortem in as many areas in your business as possible. And that’s almost sterile, tactical tip, but to me those reflections, those postmortems, those “How did we actually do? We did that, what happened? How did we do? Can we get better? How can we get better?”

All of those things are super important in being able to ask and asking people, ’cause they won’t really tell you ’cause it’s a form of feedback. And feedback is the breakfast of champions, I would say, but it’s also one of the hardest things to get out of people.

So repeatedly asking for it, repeatedly to find a way to get it on specific things, like just the other day, I asked a team member, “Hey, you’re really good at process improvements. You’ve joined the team in the last month and a half and I would like you to almost be that cop. Like, ‘Hey, we’re screwing up here’ or like tell us where we can do better on process.”

One of the things that I’m working on, process is what’s required because we’re going from an early stage to a more scale-able, repeatable execution. And this person was brought in mostly because he’s very good at that, but if I don’t ask him- the team doesn’t ask him — he’s not gonna mention it. It almost needs to get annoying to the point where I’m asking him and annoying him and I’m always at it like, “Hey we can do this better. Oh, this isn’t right, right?” Things like that. So, that’s another aspect of what I mean, because that’s almost a reflection. It’s like, “Help us reflect on something we suck at today. You’re good at it. You’re great at it.” So whoever’s great at something, make them be the cop, so to speak.

I think the third one is this word “outcome” is not used enough, in my opinion. And outcome isn’t just about your business, it’s also like, if you wanna be nice to somebody, if you wanna be honestly nice, talk about what their outcomes are. “What’re you looking to accomplish for the business? What’re you looking to accomplish for yourself? And how can I and the business help you get there?”

And sometimes people don’t know what that is when you ask them, “How can I help you get what you want in life?”

Claire: Exactly.

Hiten: Because you’re working here to get what you want in life. You’re not just working here to work here and accomplish what we want to work on as a team. There’s something you want in your life and I don’t really care what it is in the sense of not telling me, or it being private, or whatever. Tell me and I can help you get it. And that’s an outcome, too.

Claire: Yes, absolutely.

Hiten: Then you’re being honest.

Claire: Yes.Absolutely. There’s this book called The Fifth Discipline that talks about this and the word that the author, Peter Senge, uses to describe it is, he uses “vision.” So, that picture of a better place, like “if everything goes well, this is where we wanna be.” It’s vision and then the team obviously has a vision for where they want to be. You’ve got your current reality and your vision, but everyone also has a personal vision, and the role of the leader is to actually take those personal visions and somehow align it to that bigger vision. But you’ve gotta know what those personal visions are. You’ve gotta know what the personal outcomes that people desire.

Hiten: Yeah.

Claire: I’m so in line with that, Hiten, and appreciate so much all your insights. I know all those watching — at least folks who consider themselves nice — can relate and have found your thoughts helpful. Thanks so much.

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Watch our lessons for leaders: The Heartbeat Interview ❤️ with Jordan Buckner, Founder + CEO of…

As a Forbes 30 under 30 founder of a two-year-old snack company now sold in Whole Foods, Jordan shares the importance of vision yet remaining flexible as you pursue it.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Jordan Buckner, Founder and CEO of TeaSquares. Watch & read what he has to say here…

Claire: Hi, everyone. I’m Claire Lew. I’m the CEO of Know Your Company, and today, I am thrilled to have with me, Jordan Buckner, who is the founder and CEO of possibly my favorite snack on the planet, no exaggeration, something called TeaSquares. I promise, by the way, Jordan has not paid me to say this. They’re truly my favorite snack — they’re really good. They’re exactly what they are called, tea snacks, and they’re going to found in Whole Foods, now Marianos.

Jordan is an entrepreneur based here in Chicago. He started his business just two years ago, and it’s already expanded nationally, as well as was on the Forbes 30 under 30, so just really thrilled to, yeah, have you here, Jordan.

Jordan: Thanks to be here as well. It’s always a ton of fun to find TeaSquares lovers. I will say once you actually have them, they’re kind of addicting, so you can’t stop, so I don’t blame you there.

Claire: True. Very, true. I’m here though not just to plug TeaSquares or just to talk about how delicious they are but to actually ask you, Jordan, this one question about leadership especially as a young founder who’s been doing this for two years. It’s a food business. It’s different. So, curious to know, in your opinion, what’s been one thing you wish you would have learned earlier as a leader?

Jordan: I think it’s really tough for any entrepreneur to launch into a new product, new business without having any hard experience. I was actually new to the CPG, consumer product good space as a founder.

Claire: What were you doing before?

Jordan:I was actually working as a consultant in the food industry, so I knew a little bit about it, but I never ran a business myself. And so jumping in, I’m very much a idea person and could see all the pieces in the industry to think that a lot of people are snacking on to go and eating healthier snacks and looking for ways of getting a little bit of boost of energy. I kind of had that vision of a product that could satisfy all those needs, but actually building a team and building a product around it had a ton of difficulties in terms of taking your vision and executing that into reality with a large team as you grow.

The hardest thing that I wish I kind of knew was experience with working with others and bringing them along with your vision because it’s one thing to have it within your own mind. It’s difficult to bring others along with that vision as well when they have their own motivations along.

So that’s definitely been a big learning experience for me yes, but a lot of fun at the same time.

Claire: No, totally. I think it’s really interesting how you talked about, or self-identified very much with being an idea person. I think for a lot of founders and a lot of CEOs, when they first start out, they see themselves as that idea person, and then there comes a point where there needs to be a switch. You talked about how that switch from idea person to actual execution and motivating the team is challenging. Do you remember when that happened? Was there something at some point in the business, was there sort of a point of growth, or was it more gradual? Talk to me about like what was happening when you came to that realization.

Jordan: Sure. Two years ago when I started the company, I kind of knew early on that while I could launch into this on my own, that it would be really helpful to have a great team around me that could complement the skills that I didn’t necessarily have.

Claire: What are some examples, by the way, of like maybe, yeah, some of those skills?

Jordan: Definitely. I’m definitely more of the visionary. I can see the consumer problem and design solution to actually solve that problem in the market, but on some of the areas that are, say, not my expertise are just execution day-in, day-out. I like coming out with new ideas, and then once that happens, having other people that can help support executing those ideas is really valuable for me.

Claire: Yes, got it.

Jordan: When I was looking for team members and a couple of friends and colleagues who I actually always want to start a business with because we had similar values and similar ethics around creating products that really enhance the world around us while also doing a good for the world as well through their various social aspects, and so I actually found my team members first based on complementary skills. I brought along three other co-founders in starting the business that had skills across sales, operations, and design, and to help complement those skills.

Then, also, when we started the company, we want to really help young underserved individuals to provide learning opportunities for them. Part of our company mission is a social mission to help employ underserved neighborhoods, so we actually have a fellowship program, and hire young adults. We can teach them business, sales, and operations, so skills that they don’t necessarily have the opportunity to learn in school.

After taking the founders and pulling us all together around the common mission, then we have to go about building TeaSquares, building the company, and solving that problem in market. That was just a big learning opportunity for all of us, so running into challenges with manufacturing, with sales, with getting into our first retailer. For all of us without experience in the food industry, it was a huge learning opportunity, and we’ve just been continuously learning and growing ever since.

Claire: Absolutely. I love your approach around how you found those team members around values, right? I feel like values in the leadership space, to be frank, it’s such a fluffy word.

Jordan: Oh, it is. Yeah.

Claire: Yeah. I’ve written about values. I think you go to any conference or you meet any business article or book, and we talk about values but for you, Jordan, what do values actually mean, and then what are your values at TeaSquares? I have a lot of questions. I’m sorry. We’ll start with those two, and then I’ve got one more. How about that?

Jordan: Definitely.

Values, to me, mean how you conduct yourself and how you conduct your business– so the attributes and the method that you actually execute your vision to the world.

At TeaSquares, we have two visions, one being to create products that enhance people’s lives. For us, that means having a healthy snack that is filled with natural ingredients, not artificial ingredients, and then also having an energizing aspect that helps people fuel their passions in life through the organic tea. Then, on the other side, we have a social mission to fuel economic development and for us, it comes from a place of mentorship where all of us, as founders, want to give back to our communities and take all the knowledge that we’ve learned and help teach others as well. Those are the two biggest values that we have at TeaSquares.

Claire: I have so many thoughts around this. I’m just like, which question do I want to choose? The first sort of thread I want to pull on though is just how big of a deal the social mission is as part of your company. Keep in mind, everyone, this is a snack company, and you’re talking now about wanting to truly and deeply impact underserved communities and right here in Chicago. One of the things that, yeah, really compelled me to want to bring you here and to be on the Heartbeat is because you actually employ folks from the South Side of Chicago to help make the TeaSquares. I just think that it’s so incredible that that’s a value that you’ve chosen. That’s something that you’ve actually hired for.

I guess my next question is, how do you know if someone has that value? When you are hiring and choosing, not just founders but frontline employees, even choosing folks who are going to be part of your fellowship, how do you know if they sort of embody those two values?

Jordan: At the very beginning, we’re bringing on new partners in the organization or new employees. We actually go through a pretty extensive interview process where we learn not only their skillsets and attributes but their motivations in life and what’s actually driving them to achieve the things that they are.

Some people are driven by higher morality values in terms of the effect they want to have on the world. Other people simply need to make money to support themselves to support their family. All those are completely legitimate, but in the people we’re bringing into TeaSquares, we want them to be invested in the product, invested in our mission of fueling people’s passions.

That really comes out and manifests itself in the way that they work within the organization, the way that they manufacture the product, and social kind of good that they put out into the world.

In addition to the interview process, we actually work with everyone on a limited basis to start to say, how do you fit within our organization? Is this the right fit for you and what you’re looking for in your life? Is this the right place for you to grow? If not, it’s very clear to say, “Hey, no worries. If you’re not kind of bought into our social mission, how we do business, that’s fine. It just isn’t the right place.” There’s other choices that might work, but for those who have a strong passion for wanting to change the world and create really high quality products, that’s the organization we’re trying to build.

Claire: Totally. It sounds like you do some sort of test trial to actually see what people are motivated by. I also really appreciate the fact that you’ve drilled into uncovering what someone’s motivation is in hiring because I think that’s also one of the most overlooked things when it does come to hiring. Personally, one of the best pieces of advice that I got around hiring and interviewing and trying to figure out what motivates someone is I had a mentor of mine who told me all the questions that that you want to ask, the truth is revealed if you ask about what they’ve done, not about what they’re going to do.

A lot of times in interview questions, I think we have a tendency to say, “Oh, what if you’re in this situation,” or, “What if you were given this amount of money?” hypotheticals. A lot of people can say lots of things when they’re hypotheticals, but when you ask about the past, what have you done? What someone’s track record been? That often reveals a lot going forward. Would you agree with that or what do you sort of think about when you’re actually in that interview process?

Jordan: Yeah. I would wholeheartedly agree because if people are truly motivated about something, they will find a way to make it work and turn that vision into reality, so if you ask about their track record and they’re motivated about some type of social mission or affecting change in the world, they’ll have examples of how they’ve done that during difficult situations.

That’s what we hire for: Not just what would you do in a perfect world, but what would you do in an imperfect world because that’s the reality we exist in.

Claire: Definitely. Jordan, I want to rewind back to before TeaSquares was in Whole Foods and in Marianos, and soon to be in Jewel, and this was just an idea. What were the biggest challenges that you ran into, and what advice would you have for any aspiring leaders who would face some more challenges?

Jordan: In starting a new business, there’s always going to be tons of challenges along the way, and just like in every industry within food and without, being an entrepreneur is a roller coaster. There’s constantly going to be highs and lows and learning opportunities throughout. The biggest thing that I would say with that is, understand that you’re on a journey and really enjoy that journey along the entire path of running your business, and then also be open to working with mentors and others who know a lot more than you do. In starting with this new space in the snack industry, there’s a whole lot of people that knew a whole lot more than I did.

I actually sought out mentors and sought out experts and advisors who were experts in manufacturing and marketing and sales, and so for instance, joining a program here The Good Food Business Accelerator that’s partnered with Whole Foods and a large number of food industry companies to actually learn specifics around running a food business, doing finance within the food industry, sales and marketing for food specific industry components, and that wasn’t extremely helpful. Not only that, but it allowed access to a larger cohort of other entrepreneurs who are doing something similar. I now partner with about a dozen or two dozen companies that work together to foster what’s called the good food movement, so good food that is healthy and impactful on the body and also the community. As entrepreneurs, we share resources together to help further the growth of all of our businesses.

Claire: Totally. I want to go back to that first sort of piece of advice that you gave, which is to enjoy the journey. Did you not enjoy the journey or tell me why that, to you, that’s something you want to be sharing with, with our viewers here?

Jordan: Definitely. A lot of first-time entrepreneurs or if you’re thinking about starting a business, you’ll think about what the end result is, so I want to have a nationwide company that’s selling to millions of people or I want to be a millionaire.

The path to get there is never a straight line. We’re used to seeing hockey stick projections in every investor presentation that say, “I’m going to start with one customer today, and a million customers tomorrow,” without having a clear path to get there. The journey is often along a timeline that you don’t get to control in terms of when new customers come and use your product, and figuring out any pivots that you have to make and tweaking your value proposition.

If you’re only focused on the hypothetical end destination, it’s tough to navigate all the ups and downs along the journey for the entire way.

The other thing is that there is no kind of green pastures in the distance that one day, you’ll just make it to and everything will be perfect. No matter what scale your business is in, there’s always going to be larger and larger problems to solve, and so the best entrepreneurs enjoy solving problems, and then moving on to larger and bigger problems. That’s the only way to really kind of enjoy the entire journey and process, and manage the low points.

Claire: Absolutely. I think it’s such a fascinating duality to hear as a, I mean just as a fellow CEO who feels like your tunnel vision, in some ways, is your best asset, right? It’s what is going to let you see a path to something that other people don’t see. Yet at the same time, to what you explained, when you are so locked in, you can’t adapt and change the things that you’re not necessarily always paying attention to. To the, just pure … Like you’re saying, there’s so much outside of your control. I just think that the process of leading a business, starting a business is, it’s like trying to hold and juggle two different parts of one and this duality of, you know what, you have to be super focused but you can’t be too focused, and you want to be enjoying every part of it.

Jordan: Exactly. Now, have you found times where it’s beneficial to have a tunnel vision, and other times where it’s beneficial to step back from that?

Claire: Absolutely. Well, what’s interesting is I think, as a leader, you have to be a little bit delusional to see things that other people don’t see. There’s a reason why current solutions don’t exist in the world. It’s because people don’t believe that they can happen, so you have to be crazy enough in some ways to think that it’s true.

When I first took over the CEO of Know Your Company and before that, as a consultant helping CEOs create a better work environment for their employees, a lot of people just didn’t think it was that possible to create a work environment where employees can be heard. I had the sort of tunnel-vision enough and crazy enough about this problem that I thought a solution could exist, and that you could do technology in a way that was friendly and not for “Big Brother-ish”. That it could be really, really easy.

That was to my advantage there, but that tunnel-vision and the delusion, if I held on too tightly to it, then I wouldn’t understand how the market’s changing, what my customers actually want, how competitors are also sort of also plying the space. When, as a CEO, as a leader, if you’re not able to see that reality for what it is, it’ll come up and surprise you.

Jordan: That is so true. Two things you mentioned as well, which was having and identifying a problem. That was a really big important problem that already existed, and then having a strong vision on how that solution could be better and how the world could be better.

What I’ve been experimenting with and really understanding and learning is that it’s good to have a tunnel vision to that vision of what the future will look like, but then natural ways and means of getting there and having some flexibility and adaptability to change along the way.

Claire: Absolutely, so clarity on that, and vision, but not an obsession that it has to exactly be that, nor should the path have to go a certain way to get there right. I love that. Well, Jordan, thank you so much for sharing your insights around vision, around hiring, and just around how to start a company, especially a successful snack foods business. It’s been awesome to have you on.

Jordan: Definitely. Thank you so much.

Claire: Cool.

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Watch our lessons for leaders: The Heartbeat Interview ❤️ with Aynn Collins, Director of Talent…

An expert on employer brand and recruiting at the 900+ person company, Mailchimp, Aynn shares what she wishes she learned earlier as a leader around failure and vulnerability.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Aynn Collins, Director of Talent Strategy at MailChimp. Watch & read what she has to say here…

Claire: Hi, everyone. I’m Claire Lew, and I’m the CEO of Know Your Company, and today, I am so excited to have with me, Aynn Collins, who is the Director of Talent Strategy at MailChimp, possibly one of my favorite companies and a lot of people’s favorite company. I happened to meet Aynn at a conference this past year in Austin, and it was amazing to hear, first of all, what her role is in the organization.

As the Director of Talent Strategy, with MailChimp now being 900 people and counting, she manages employer brand and the employee experience. I’ll let her talk a little bit about that, but really excited to have her here and to ask her this one question about leadership. Aynn, thanks again for joining me.

Aynn: Thank you for having me, Claire. I enjoyed meeting you at Culturati Conference as well, so I’m flattered you wanted to talk to me.

Claire: Oh my gosh. Of course. All right, Aynn. I’ve got this one question for you about leadership, and it’s if there’s something you wish you would have learned earlier as a leader, what would you say that is?

Aynn: That’s a really good question, so kind of talking to my to my younger self about leadership, it sounds like you’re asking me. That’s funny you asked me that because here at MailChimp, I end up talking with a lot of employees here about things I learned early in my career, whether it be leadership management style, feedback, what-have-you.

I think I would tell my younger self to really embrace failure. You learn much more from a single defeat than from a thousand victories.

Obviously, nobody’s excited about failure or not meeting a goal, but not sweeping that under the rug and talking about it, so just really embracing failure and understanding how you learn and grow from those failures, I think is what I would tell people to learn early in their career. They can own failures, talk about them, debrief with your team on, even if the whole project wasn’t a failure, what that have done better, and not try to just make everything shiny and pretty. Because we know business and leadership is not always perfect, and shiny, and pretty. We all have failures all the time personally and professionally, and I think that’s something that I really encourage people to talk about.

In fact, yes we introduced a really cool program here last year. Part of my role is employer brand, so really amplifying what makes MailChimp a special place to work to the outside world.

I think the key to an authentic employer brand is making sure that you’re really telling the true story, like don’t make it too perfect. Make it who you are.

The best way you do that is to get employees out in the wild talking about MailChimp, whether it be technical talks or speaking about our culture or just being an ambassador when you’re out a conference or out in the wild.

We have this really cool speaker training program at MailChimp, and one of the things we did last year is introduce an internal program called Fail Tips. It’s basically a lunch and learn format where six to eight employees do a five-minute or less talk on a personal or professional failure. You wouldn’t believe the waiting list I have for people that are willing to talk about their failures and how they learned and grew from that. Yeah, that’s definitely something I think we’re doing well at MailChimp is looking at how we can do things better and not sweeping the things that didn’t go well under the rug.

Claire: Absolutely. I love this topic of failure when it comes to leadership because I think you talk to some entrepreneurs and some leaders, and they’ll tell you that they actually don’t really even believe in the word failure and that there’s no real failures but all they really are really expensive mistakes. A lot of leaders actually even reframe the way they look at failure as just saying, “Well, no. This is just how you actually learn.” Failure has just such a negative connotation, and so I love your emphasis on this.

I’m curious, Aynn, so for you personally in your journey and career as you become a leader, when did this click for you? Did something happen or did you watch something unfold or did you experience something where you went, “Oh my gosh, I need to wake up and make sure that I’m not sort of sweeping failures under the rug”? When did it really hit you how important this was?

Aynn: I’m not sure there was a specific “aha” moment. You’re still feeling the pain of the failure about four or five different things but I can remember, at a different company, this is not at MailChimp, where I was head of recruiting. We had to hire. We were hiring a leader in a role that was sort of struggling. It was a young startup, and we felt like we needed somebody with a stronger personality to really motivate people. We interviewed and hired a woman that had a very strong personality that, at the time, seemed like the fix. Once we got her in and on-boarded, it became apparent quickly that her style was just too different than our cultures and that she wasn’t listening to that culture and sort of adjusting her style, and instead of motivating the employees, which is what we really wanted her to do, she was demotivating.

Our executive team at that company made a really good quick decision to go ahead and terminate that relationship, and then talked to that team about our failure to them. I think being very, very clear about we made a mistake and this is what we’re going to do differently in the next hire, we’re going to listen to your feedback because there was some concern from this person’s direct reports during the hiring process that it was too different than our style, and we glossed over that. They were very appreciative of that.

I always feel like, that even here at MailChimp, when we push something too hard and didn’t get the right feedback, when we stop and listen and say, “Wow, you were right. We really should have asked you before we implemented this policy. Let’s change it,” you get this level of forgiveness and trust from your fellow employees when you admit that failure and adjust that you just can’t buy. That’s probably the best way we’ve built trust here and in other roles is by admitting our shortcomings and adjusting quickly.

There’s a story of many years ago where a hiring failure sort of taught me a lot. I actually, in between that company and coming to work for MailChimp, I had a small business failure, so I started a line of clothing for mothers. It was clothing and fun accessories. It was going very well, and then 2008 happened. I decided to close that business. It was very painful because I had really aligned myself with that brand. I was very proud of that, but I made a tough decision to quickly get out of that, and that was that. It was really hard for me. It’s still sometimes hard for me to even see references to that part of my life and be like, “Oh, that was so …” but what I realized actually when we did this fail tips program, and I bared my soul to the MailChimp employees and told them how hard that was is that, well, it led me to MailChimp.

MailChimp’s vision is to empower small businesses. It’s to empower the underdog, which in our definition is small businesses, so I feel that pain. I can empathize with small businesses now, and even though my role is not directly product focused, it makes me really aligned with the company I love. If I hadn’t had that small business failure, I wouldn’t know the things small business owners have to do every day just to keep the lights on. That failure led me to MailChimp. I know I’ll have more failures, right? I think I’m that more resilient. It made me that much more humble. It makes you think. It makes you get more input and feedback before you make decisions.

I am not a failure but I embrace failure.

Claire: Absolutely. I mean, I think both those stories are sort of amazing windows into understanding how unexpectedly, failure leads you to your point of greater feedback, greater insights, better decisions, and then also just ultimately a better path for what you want to be doing. In the moment, it never feels like that. Let’s be clear so that everyone who’s watching, it never feels like that in the moment.

Aynn: It feels terrible.

Claire: Yeah, so my question to you, Aynn, is then for current leaders and aspiring leaders who are watching this and who struggle with being vulnerable, who struggle with … who maybe, I mean let’s be real. They’re in a high-pressure situation. There’s maybe a lot of money on the line. There’s a ton of competitors. Everything needs to be moving really quickly. They’re trying to attract and retain the best talent. How can you afford to be admitting all the time all your mistakes? What would you say to anyone who’s watching who’s skeptical about sort of doing this in practice?

In theory, it’s great. It sounds good. Maybe doing it here and there once in a while is good, but you’re talking, I think about being a lot more rigorous about admitting shortcomings and failures. What would you say to anyone who might be sort of skeptical about doing this in practice?

Aynn: Yeah. I think with anything, you have to apply sparingly. Your team needs to have confidence in you, and we certainly don’t have to show every bit of vulnerability but vulnerability goes so far in leadership, I think. I think what I found is when I have leaders that I work with or support do admit failures or shortcomings or missteps, sometimes it’s just a misstep, it’s not a full failure, that you really get this loyalty from your employees that, again, I think I said earlier, you can’t buy or you can’t teach. It really rallies them to get behind you and help you and the entire organization not let that happen again because failures should not be repeat failures.

You should learn from every failure and think about how you’re not going to let that specific failure happen again. If you have confidence in saying, “This is where we screwed things up. Here’s how we’re not going to do it again,” I think you get the most amazing engagement with the people you manage and lead.

Claire: Absolutely. I think as leaders, we can be often hyper self-critical so to sort of admit every single small dent in the porcelain isn’t what we’re going for here, but to your point, I think one of my personal greatest sort of moments of progress that I’ve made as a leader is I remember we made a really big mistake with Know Your Company maybe three or so years ago with our code base. We accidentally revealed all these private answers that people weren’t supposed to see. It was this huge mistake, and it affected hundreds of CEOs.

There were two options. We could either tell folks that this happened because people weren’t aware — no one noticed it. Or, we could just not say anything and just fix it and move on.

We had a really big debate about this with our team internally about what we should do. I remember what we were faced with was, well, do we admit it publicly or just, yeah, is it fine and should we just gloss over it? What I ended up doing is I remember calling Jason Fried who’s the CEO of Basecamp, and he sits on our board. I remember calling Jason and telling him the situation. All he said is he asked me this question, Aynn, which he said, “What kind of company do you want to be?” He said, “I love situations like this because it forces you to ask that question.”

The minute he said that, that’s when I knew what I was going to do. I decided to be really transparent about what happened. I told all our customers exactly what happened, and the response was fascinating. I braced myself expecting it to be angry, and to your point, it was the exact opposite. People were so appreciative. They said, “Claire, thank you so much. Mistakes are made while you’re doing work. Don’t even worry about it.” It created this greater sense of loyalty.

Almost what that story to me makes me think about is it’s not just asking the question what kind of company do you want to be, but it’s also asking the question what kind of leader do you want to be. To your point, Aynn, when you’re in those moments of, “Oh, should I say something or should I not?” asking that question can hopefully help people decide whether or not to divulge something, so thank you for, yeah, for sharing that.

Aynn: Yeah. I think that’s a great story, I always tell I have two teenage daughters, and I tell them a lot. I’m sure they get annoyed by it.

I always say, “Don’t just be good on paper. Be good in real life.”

That is an example of being good in real life. I think people trust you. I mean, your customers probably have this greater sense of trust with Know Your Company when you’re going to tell them something like that.

Claire: Yes, absolutely.

Aynn: It’s such a great story.

Claire: Well, thank you. You fall flat on your face and you learn from it. One last question for you here, Aynn, because you are such an expert around thinking about the employer brand and how you, to your point, take what already exists within an organization and expose that outward.

When it comes to being vulnerable, when it comes to failure or just in general, what should leaders who are watching this who unfortunately don’t have you on their team and a director of talent strategy on their team, what are some things that they should be thinking about, small things, big things, to create an employer brand that really reflects what their true experience as employees are?

Aynn: I’ve been in this role two years at MailChimp, and I handle things from what does our jobs page look like to from a social perspective, how do we show what life at MailChimp is like, to how do we show up at conferences. For instance, we are a huge fan of the Grace Hopper Conference. It’s all female engineers once a year. How do we show up there authentically and really support, not just hiring people but the community? MailChimp’s very into community and supporting community side of things, and how do you do that in a way that attracts people that would be a great cultural compliment to MailChimp but that is true to who you really are?

Knowing your company. There’s a little pitch for you. Really understanding what your values and vision and mission are and making sure that’s woven into everything you’re putting out there about your employer brand. Really, I think the mistake a lot of companies make is making it glossier and prettier and idealistic like what they want to be.

I think it’s much better to put a great realistic view of what it’s like and how people get here, decide to join you and buy in that it’s actually much better than they even thought and that you really are living true to those things.

Not pumping things up too much, not selling perks and things that aren’t that important to your culture but really selling like, for us, it’s that connection with a small business owner. It’s being really engaged in community. It’s giving employees impactful things to work on. It’s not the ping-pong table because we have that. It’s not the benefits that we have are great. It’s really the type of work and the type of people, and the engagement you’re going to get here.

We constantly ask new hires. We have a great onboarding program. We constantly ask them like what brought you here, and what surprised you now that you’ve been here for a month? We get great answers. Sometimes like, “You know, I kind of thought I’d be working on this, and once I got here, I figured out this is how you do things.” We love it when an employee feels comfortable enough after 30 days to say, “It was not quite what I thought. Maybe you shouldn’t put this out there about yourself.”

Claire: Yeah.

Aynn: Talk to your new employees. You’ll get a great feel how your, what your employer brand is like if you get them in the first week and then say three months later to say, “Are aligned to what we’re putting out there?

Claire: Right. No, I love that asking that question two to three months later of what surprised you now that you’ve been here. That really uncovers what’s the disparity between your perception of the company and then the reality and then doubling down on, okay, what’s real. I think that’s immensely helpful. Well, Aynn, thank you so much.

Aynn: Yes.

Claire: For your thoughts. I’m sorry. I kind of cut you off there.

Aynn: No. No. I was going to say like I think especially today when so many are so focused on diversity and inclusion, and especially the inclusion side of things, that’s really important, your brand. Did people feel like they’re part of the story when they get here?

Claire: Absolutely. Absolutely. Thank you so, so much for everything you shared. It’s so helpful to think about and rethink failure, and make sure that we’re prioritizing how we talk about that. Then, so many great insights about making sure that our brands as companies are true, and not just what we want them to be but are real so thank you so much again, Aynn. We so appreciate it.

Aynn: You’re so welcome. Thanks for having me.

Enjoy this interview with Aynn? Check out all our Heartbeat interviews with leaders…

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From the Heart(beat) ❤️: Leadership tips for new managers

I share a few of my favorite latest leadership tips from CEOs, founders, and executives featured in our Heartbeat interviews.

What do you wish you’d learned earlier as a leader? Every two weeks, I ask this question to a CEO, founder, or executive I admire in our interview series, The Heartbeat. The answers are sometimes surprising, counterintuitive, or relatable — but always fascinating.

I thought I’d share a few highlights of the tips they have especially for new managers just starting out…

  • David Cancel is CEO of Drift, a sales conversational marketing platform with more than 10,000 customers. David has been an entrepreneur for most of his professional life, having started five companies before Drift. What does David wish he had learned earlier in his management career? It’s all about people:

“It’s 99 percent people and 1 percent everything else…I think basically it’s the communication…We don’t really understand that everyone is slightly different or wildly different and that they need to be communicated to in different ways and absorb information and communication in different ways.”

  • Elena Valentine is the founder and CEO of Skill Scout, a media company that helps transform hiring and recruiting for organizations through video. For Elena, figuring out her true leadership style was a struggle for her — and it started to click the moment she stopped comparing herself to other leaders.

“It took a really long time to realize that I was comparing myself to elephants when I was really a giraffe and I needed to find other dope giraffes. And that took me probably up until the end of last year to really follow my true north and see that I’m a giraffe, I’m proud to be a giraffe and there are businesses that are incredible, that are run by giraffes.”

  • Steve Larosiliere is the founder and president of STOKED, a nonprofit organization that helps teens stay out of trouble by getting them engaged in action sports. Most recently, Steve and STOKED were featured on NBC’s TODAY Show for the impressive work they’re doing. What does this nationally-recognized leader wish he had learned earlier?

Empathy. I feel like early in my career, I didn’t have good leadership role models. I thought leaders just barked orders. If they were the leader, and they had the vision, everybody needed to fall in line. That is completely wrong. I think I’ve developed empathy throughout the years, because I realized that by putting yourself in other people’s shoes, and knowing where they come from, and understanding who they are, their motivations, their drive, their strengths, their weaknesses, their hopes, their fears, if you get that, then you can work with people.

  • Katrina Markoff is the founder and CEO of Vosges Haut-Chocolat, an international chocolate company that exceeds $35MM in revenue annually. Katrina has also been featured on the Food Network, not to mention countless of publications like Fast Company, Inc, CNN, and Glamour. Having grown her company to 130 people and counting, Katrina gave some advice about the challenges that come with added people, structure, and hierarchy in a team:

“Sometimes having these titles makes people feel like they’re so much further away from you than truly they are. Just really approaching it on a human level like, “How are we doing this together? Let’s figure this out.” I think that empowers people when they know they have a voice to you, especially with people that are new.”

This just scratches the surface of what we’re learning from these inspirational leaders and executives. To hear their full stories, sign up for The Heartbeat, our free biweekly newsletter that touches on leadership, employee engagement, company culture and feedback.

And, take a peek at some of our other resources we offer leaders…

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @cjlew23.)

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Katrina Markoff, Founder + CEO of…

As the creator of a luxury chocolate empire exceeding $35MM annually, Katrina shares insights on what not to forget as a leader, and the importance of knowing what you’re NOT good at.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Katrina Markoff, Founder + CEO of Vosges Haut-Chocolat. Watch & read what she has to say here…

Claire: Hi, everyone. I’m Claire Lew and I’m the CEO of Know Your Company. Today I am thrilled to have with me the one and only Katrina Markoff.

If any of you have ever heard or eaten Vosges chocolate which I have in my kitchen all the time — this is my favorite bar — Katrina is the founder and chocolatier of this amazing brand.

She studied in Paris and built this company from the ground up. It’s all about this ethos of being able to travel, in many ways, when you eat chocolate. You can find her chocolate in, obviously, high end boutiques all across the world, but I think the thing that’s really unique about what you do too is you also make it very accessible. You actually have locations at O’Hare International Airport. You distribute your bars also through Whole Foods.

And then something that I actually learned today that I had no idea about is, she recently launched a new brand of chocolate called Wild Ophelia and all the proceeds go towards an accelerator that they have for young women entrepreneurs in high school that are in food businesses.

Katrina: High school and college.

Claire: Absolutely amazing. I know you’ve also been on the Food Network and in all these publications. Katrina is the real deal. She’s based here in Chicago. I’m lucky to know her and I admire you a lot.

Katrina: Thank you so much, Claire.

Claire: Oh, my gosh, of course.

Katrina: It’s great to do this.

Claire: I’ve got this one question to ask you, Katrina, about leadership and that is, what’s one thing you wish you would have learned earlier as a leader?

Katrina: I think the importance of staying really close to your leadership team, really aligned and really close. As your business grows from entrepreneurial startup to much bigger, wider teams, you’re pulled. I’m pulled so much as the founder and the face of the brand into being PR focused and speaking focused and whatnot. And I would say, it took me a lot out of the company and I am naturally an introvert.

Claire: Oh, really? I would never have guessed that. Me too.

Katrina: So I’ve learned through bumps and hills and valleys that you can’t lose that connection with your team because it’s so often they’re working for you, for your vision. That connectivity to you is part of the reason they’re there.

So as you get drawn more and more out, you have to remember how do you connect again.

That is in ways of lunch or getting feedback or social outings with your team. I think that’s important, not to lose sight of that. It seems maybe that’s obvious, but actually –

Claire: It’s hard.

Katrina: … it’s hard.

Claire: It might be obvious, to your point, but it’s hard in practice. I think everyone who’s watching this is probably nodding their heads going, “Oh, yeah, as a CEO or as a leader being out, doing, speaking, being out promoting, etc, you forget to reconnect with the team. For you though, how big is your leadership team? How many people do you have? How big is actually Vosges as a company right now?

Katrina: We probably have around 100 employees and it flexes up depending on the seasonality because we make a lot of chocolate during the holidays and so it goes up. But in reverse, it’s the core group of leaders in the organization, maybe there’s eight to 10, but those are very important eight to 10 people that need to feel like they’re important to you. I had kids too which is a whole other level of distraction from being a founder, single, then got married, then had kids. All that stuff is taking that part of you. I think the more you can set up those connection points with your team and also, of course, hire the right people who are very entrepreneurial in nature, as I like to say, or take a lot of initiative, more the type that maybe you need to pull the reins, but less that you have to push up the hill and that need a lot of feedback from you to make those decisions. Figuring out how you change your team over the time of your life with the business and its initiation stages to the more mature space.

Claire: Absolutely. No, that makes so much sense. I have a million questions I want to ask you.

Claire: The first part is around, you’re talking about connection points, building connection points. So when you were saying, “Oh, it could be as simple as lunch.” Is there anything you do particularly right now with the Vosges leadership team that might be considered counterintuitive about connection points or what do you try to do as a leader to make sure you’re staying in contact with folks?

Katrina: One of the things I’ve been doing lately is really having the level playing field conversations like, “Please give me feedback. What are your ideas? How could we make this better? You tell me, give me feedback. Please give me feedback. What do I need to be doing better?” Because I think the more down to earth and approachable they think you are, the better it can gel. I don’t like top down organizations. People that are on the floor making the chocolates to people that are running those teams, they see so much that I don’t see as much anymore. I worked in every area before which is super helpful to know how everything works, but then you get a little bit distance so you need to get their feedback and how can they feel comfortable giving you that information.


Sometimes having these titles makes people feel like they’re so much further away from you than truly they are. Just really approaching it on a human level like, “How are we doing this together? Let’s figure this out.” I think that empowers people when they know they have a voice to you, especially with people that are new.

And also with all the new hires now, I’m spending time with them, just even 15 minutes the first or second week it’s like sharing my vision, getting to know who they are, what are their interests and really trying to connect so there feels like there’s a trust.

Claire: Absolutely. Well, I think one benefit that you probably have in building that trust is, you do run a chocolate … how many of us run a chocolate company in the sense of the vision that everyone is gathering around and excited about is pretty aligned. Do you ever find any challenges though in the sense that because it’s food, because it’s chocolate, which is so pleasurable and won- … I mean, chocolate’s one of my biggest loves in life. Do you find any tension around the fact that, “We are running a chocolate company, but at the same time, how do we make sure everyone is one the same page. I’m curious about that.

Katrina: When you first start, there’s chocolate everywhere and it’s really fun, but it’s definitely a business too. It’s really fun, but it’s like how are we really focusing on the goals for each channel because there’s so many channels within the business. It’s fairly complicated in that way because we manufacture in-house, we do sell to other retailers like the Whole Foods of the world and Kroger’s. Then we have our own retail boutiques and we have our own e-commerce and we have our own business development, own hospitality and events, now we’re opening up our Chocolate Temple to the public. So there’s a lot of complexity which makes for a really beautiful deep brand with a lot of story, but also complexity.

Claire: It’s almost like seven different businesses that you just described to me.

Katrina: Seven different little businesses.

Claire: Absolutely. One of the things that you also mentioned too in managing that complexity is, you were saying, emphasizing the important of who you hire. And I loved what you said about finding people who you have to pull the reins back on instead of push up the hill. Can you tell me a little bit about that? When did you realize that was important? Did something happen or-

Katrina: Yeah. I would say when I first started, I remember thinking, “Well, we couldn’t really afford to hire people that were too expensive. So we would hire-

Claire: I think we can all relate to that, all of us watching this.

Katrina: You’re building a brand and there wasn’t this huge foodie movement when I started and now it’s pretty sexy being in the food business. In the beginning, it was just like really working side by side with them and showing them and then having them do it as opposed to necessarily hiring expertise that I was going to learn from and that was going to take off and just go. I think as we got bigger and I couldn’t be in all the areas, it seemed clear to me that it was more and more important that people were driving it, that were taking the reins and doing it. I’m not the best at hiring, I’d say it’s not my skill set. Recently, a woman who’s just been an inadvertent mentor/angel decided to lean in and help me. She literally helped me hire the last three or four people and she’s really good at it. So one of the things.

Claire: What does she do that you don’t do?

Katrina: She has an innate… I don’t know, ability of how to judge people and ask questions and know who’s good. In many cases, I probably wouldn’t have hired the people she selected and they’ve been rock stars. So it’s very clear to me that it’s not my forte to hire people. That’s okay.

You have to know, probably almost more important, is to know what you’re not good at than what you’re good. You kind of already know what you’re good at.

Claire: Absolutely. I love that.

Katrina: And you can’t be good at everything. If you know someone who’s quite good at doing something you have a deficit in, ask them to help, however. In this case, this woman was so generous. She’s like, “Just throw me a chocolate party, somewhere I’ll help you out.” I’m like, “Oh, are you kidding?” Angels show up all the time and she’s definitely one of them.

Claire: That’s amazing. I think what you said about knowing what you’re not good at is almost more important than knowing what you are good at. I think that’s such an important piece of wisdom. Also, hard to do, right?

Katrina: That’s true.

Claire: Talk to me about, do you have to swallow your pride when you do that? How do you keep that in check because I think for a lot of leaders, we know what we’re good at. I don’t know if we always know what we’re not good at.

Katrina: And the thing is, you always have to have a strong face for your board, for investors, for the press, whatever. It’s very atypical to feel safe around saying what you’re not good at.

Claire: Like the fact that you said, “I’m not good at hiring,” and you’re a CEO. No, no, no, I just mean like that’s refreshing. That’s super refreshing.

Katrina: And it’s real. At a certain point, when your company gets to a certain level too, you’ve got to really know that clearly because, in my case, I’m good at getting it from zero to 30ish million, but to get from 30 to 100 is a whole different game. In fact, what I find now is that I’m setting myself up to go back to my roots which is my sweet spot which is really creating the vision, the story, the product, being the faith, those kinds of things that no one really else can do and building a team around innovation and stuff like that. Then it creates a bigger and broader group that can do what I do too. Yeah, you know when you get to these different levels, how you reassess.

Because, in the beginning, you have to be good at everything. But then, at some point, you have to say, “Really, I’m best at this and next level, I need these types of people to fill in my gaps.

Claire: Absolutely. And I think there’s something really interesting in the beginning, you have to be good at everything, but not necessarily great. Then when you get to a certain level, then you have to be actually great and world class in a few specific areas. It’s very difficult to be great and world class in everything. That’s when you need to find those people and admit to yourself, “Okay, I’m strong in this, I’m strong, I’m not.” I’m curious, for you, how do you keep that check? Do you have a person you talk to be like, “Hey, can you keep me grounded about what I’m not good at,” or is it your leadership team that keeps you in check. Is there something personally that you do and ask yourself questions. Is it an executive coach or is it a peer group?

Katrina: I’ve had all of it. I’ve had coaches, I’ve had peer groups, I’ve had my husband give me a lot of feedback. And you know, frankly, I’m fairly self critical so I have a pretty good sense of that.

Claire: We don’t need more of that.

Katrina: I’m pretty hard on myself, but where I have a ton of fire and a ton of confidence is where I know that’s my strength because it just naturally comes up and I can naturally be very strong about my opinions and I know that where there’s passion, there’s usually magnetism and there’s usually something right about that. And I’m super intuitive. I’ve been like that this whole time, about this brand. I think when I veered off from being intuitive is when I’ve made mistakes.

Claire: Interesting.


Whether it’s all these people that seem to be much smarter than me in X, Y, Z and referring to data and whatnot. It’s good to a point, but at the end of the day, intuition has to be the lead. And you have to be confident in your commitment to that. Because, in the end, that’s the thing that makes us very different from AI, very different from the computers of the world. It’s something that is a sense that humans have that we must continue to honor.

Claire: Absolutely. Thank you so much for encouraging us to listen to ourselves, to trust that intuition. I think a lot of reason why people would even watch videos like this and like The Heartbeat is because they think, “Oh, someone else has the right answer. There’s some advice out there that’s good.” And, it’s the case.

Katrina: And, it’s inside.

Claire: It’s inside. One of my favorite quick, I don’t know if you said this, but it’s just the thing I always repeat to myself is that, “Everything you think you need, you already have.”

Katrina: Exactly.

Claire: It’s all inside.

Katrina: And trust the universe.

Claire: Exactly. Well, Katrina, thank you so much for sharing your wisdom with all of us.

Katrina: Thank you.

Claire: I know we’re all walking away just reminding ourselves to think about maybe the things we’re not good at, but also at the same time, to listen to ourselves a little bit more.

Katrina: Absolutely.

Claire: Thank you so much again. And for those of you who haven’t eaten any Vosges yet today, maybe now is a good time.

Katrina: Thank you.

Enjoy this interview with Katrina? Check out all our Heartbeat interviews with leaders…

And, take a peek at some of our other resources we offer leaders…

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks😄 (And you can always say hi at @clairejlew.)

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Rob Walling, Founder of Drip (with…

As a serial entrepreneur, author, and podcaster, Rob shares his thoughts on intentional hiring, and valuing trust over loyalty first when building a successful team.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Rob Walling, Founder of Drip. Watch & read what he has to say here…

Claire: Hey everyone, I’m Claire Lew, and I’m the CEO of Know Your Company, and today I have a really special guest. I have Rob Walling, who is the co-founder of Drip, an email marketing automation software. Actually, I don’t know if you know this, Rob, we actually use Drip, your company. We love it.

Rob: You know, I didn’t. Awesome. That’s great to hear.

Claire: Yeah, and it’s actually, it’s only one of many things, or ways, that Rob and I are connected. Rob is a serial entrepreneur. He started multiple companies in the past, he speaks at a ton of conferences, he runs a conference called MicroConf which I actually happen to speak at, so just been a big admirer of your work over the years Rob. Everything you’ve built. And I know recently you’ve and your wife Sherry actually just published a book-

Rob: That’s right.

Claire: … which I highly recommend for people to check out. Just by the title. I believe it’s The Entrepreneur’s Guide to Keeping Your Shit Together. So I think-

Rob: That’s exactly right.

Claire: I think we could all probably read a page or two out of that just based off the title. But yeah, an honor to have you here today Rob. Thanks for joining us.

Rob: It is my pleasure. Thank you.

Claire: Cool. Well, so Rob, I’ve been asking all sorts of folks this past year this one question about leadership, and what it is, is “What’s something you wish you would have learned earlier as a leader?”

Rob: Yeah, it’s a great question. I’ll have to go back and listen to all the prior answers. I did not on purpose so that I wouldn’t accidentally say someone else’s.

I wish that I had learned that I didn’t need all the answers. I don’t need all the answers as a leader, and that hiring people that are better than I am at something, and then when a problem comes up looking around the room and saying “I don’t know. What do you think?”

You know, and it’s not always that. It’s not always putting it back on everybody else, but for me leading 15 years ago when I first started in my 20s, I was all nervous like “I have to be the boss and I have to know the answers and when people come to me I have to be able to say ‘Well this is what we should do.’” And over time realized “No, I work with really smart people,” especially if I’m hiring well, and my most recent experience with that is at Drip, and it’s the best team I’ve ever assembled, it’s the best team I’ve ever worked with. And now when problems come up, it is always a look around the room and saying “Someone here knows this answer. It may be me, but it’s most likely going to be one of you.” And that’s … I wished I had known that a lot sooner.

Claire: Wow. Yeah. I can totally relate. Oh my goodness. I think there’s something almost inherent in how our culture even thinks about leadership, right? That leaders know the answers. That’s the whole point. And so I love that realization. I also think something really interesting that you just talked about is how you feel like Drip, the current company that you founded, is your best team assembled to date, right? So tell me about, was it something different you then did in the hiring process or in thinking through as you’re coaching people? Why is it different? And in what was is this idea that you don’t have to be the one knowing all the answers? What role did that play in so that … you know, that’s a bold statement. “The best team to date I’ve ever assembled.” So I want to hear more about that.

Rob: Yeah. Yeah sure. I mean, there’s a couple reasons that I say that, or that I was able to build that team. I say it because it’s true, and I enjoy my work so much more working with these folks, and they’re the … whatever scale, if you were to say one to ten as developers, one to ten as co-workers, one to ten as whatever, just across the board the folks I work with now are better. And I’ve worked with great people. I’ve been coding, essentially, for 20 years, almost — coding and founding software companies for almost 20 years.

The reason I was able to do it differently this time was a couple things. One, I had full control. Like, I built it from square one. I was employee number one. Derek my co-founder. Number two, there was no one kind of foisted on me. The other thing is, since Drip did grow very quickly, I had budget to hire at a level that I used to not be able to. I used to hire a lot of contractors. I needed cheap talent because if one of my apps was making 20 grand a month, it’s like you can only hire someone so good and still pay the bills, you know? But Drip had the growth and the revenue to cover it. And the third thing is, I had the luxury. Well, there’s four things. I’m going to keep going.

Claire: Keep going. Keep going.

Rob: The third was my network was the biggest it’s every been. You know, as you said I have a conference now and I have all this history, and the blog, and the podcast and just all this stuff that I’ve done, that it enabled me to kind of have a reputation to draw people.

But the fourth reason that I think is perhaps of all those, one of the most important, is we hired slowly and we were very picky. We turned down dozens of candidates for every person that we have wound up bringing on.

And so it has meant at times we don’t hire as fast as I would have liked, and as a result sometimes the road map isn’t moving as fast as I would have liked, but it was a long term view. You know, I’ve been working on Drip for five years now. It is a long term view of, in the end five years from now this team will be phenomenal if we just slow it down a little bit, versus making that snap decision. “Well, no, just say yes to this person,” and then you’re a year down the line like “Oh my God, I’ve built a toxic culture,” or “Now I have to fire two people because they’re not working out.”

Claire: Absolutely. I think that’s tremendous advice. Almost so much more difficult to practice, than it is talking about. Because I know the temptation, especially for folks who are funded or who have the luxury of being able to spend cash up front pretty easily to hire folks. Yeah, you can’t move as fast if you don’t have the right people, so that temptation is definitely there.

What sort of checks or questions or processes did you put in place, or how did you think about consciously? It sounds like a very conscious decision of “I’m going to slow down this hiring process and we’re going to wait it out.” How do you make that call? How do you decide when that? Especially as you start off as a self funded company, right? You don’t have that luxury. You have competitors who are funded. I mean, how do you grapple with that as a founder, as a leader?

Rob: You know, I didn’t make the deliberate decision to slow it down as much as I made the deliberate decision to hire very carefully, which by its nature the result is that it does slow down. So I wish we could hire faster, but the checks as you were saying, is we have a few layers of interviews, and that first interview is all about personality, and it’s all about probing into things and catching: What are the yellow flags and what are the red flags?

If we talk to someone with no yellow flags, I’m suspicious, like we didn’t get their true self. Because if I was in an interview, you would pick up on things, and it’s like “Yeah, Rob’s really good at this, and Rob’s going to kind of be a pain in the ass about that. Rob’s not going to be great at this.” You’re just going to know. No one is infallible, and so if I don’t pick up on at least a couple, a yellow flag or two, we actually dig further. And then you just start seeing patterns.

I’ve done hundreds, literally hundreds and hundreds of interviews over the course of the 20 years of hiring developers and product people. And so I think at a certain point its trusting gut. But also we have four or five different people who talk to the candidate over the course of a couple weeks, and we do pair programming now which has been a real game changer for us. A one hour pair programming interview to look at not just the technical. It’s not “Oh, do they know the right words?” It’s like “How are they to sit next to for one hour and code with? How does that feel?” I think we really upped our game there.

And as usual, it’s, “If in doubt it’s probably a no.”

Claire: Hmm. Yeah. I think that’s so wise.

I want to go back, Rob, to the original statement you made as the answer to the question about letting go of having to be the person with the answers. Talk to me about the time prior to that revelation when you felt like you needed to know the answers. I mean, what was the cost of that? Was there some event or something that happened or a conversation that you had where it caused you to realize “Oh gosh, the whole point of having a team I guess is for me to not know everything,” or … I’m very curious about that.

Rob: What caused that mindset shift.

Claire: Right. What caused it, or if there were any … if you got burned because of it at any moment.

Rob: The cost of it was that it was a mental cost, right? It was having the burden of constantly having to go from a manager’s point of view or a CEO point of view where you’re kind of at 10,000 feet and then someone comes with something, and it’s like “Alright, I need to dig in and actually look at this code and make a decision,” right? And it’s like “Huh, this is taxing mentally,” because you only have so much good glucose in a day that you can use for interesting things or decision fatigue sets in.

So that was probably the biggest cost for me, is I just could only make so many decisions, and I was making too many I should not have.

And the tipping point was two things. One, it was eventually realizing that was just stupid, and then two it was starting to work with better people. And Derek was … was Derek the first? There was a support guy before that named Andy who took everything off my plate and I started realizing “Wait a minute, this is very interesting.”

At a certain point he’s really good, fully remote, and I’d never met him in person. We’ve worked together for eight years or whatever. He started saying “Hey, I think I’m just going to make some decisions about some stuff that I’m checking in with you.” And I was like “Fine. Do it.” And I would look back and be like, he made 20 decisions last month that prior I would have asked him to run by me, and one of them was wrong in my book, or it didn’t live up to what I would have done. The cost of that one decision compared to the 19 I didn’t have to make was just so over. It was such an offset that I was like, “This is a no brainer. I need to find more people like him, and I need to do this again.” You know?

And then finding my co-founder Derek, co-founder of Drip, pretty quickly we talked through what the original incarnation of Drip would be on my kitchen table, and then I said “All right, you let me know when you have something to show me.” It was like six or eight weeks later, he comes back, which is … I never did with developers, right? He was a contractor at the time and eventually became my co-founder. I would never do that because it was always like “Send me weekly updates with this, and the screenshot and then I can tweak the this and then copy it,” you know. And he came back after six or eight weeks and I was like “Damn, that’s really good. Let’s tweak these two things.” And it was like “Huh.” Working with someone of his caliber really makes this a lot easier, and during that time I was able to focus on marketing and all this other stuff, and so those were kind of the events that led me to that.

Claire: Absolutely. I think something that what you’re talking about, one thought that it evokes is, I talk with so many emerging managers, right? So, new managers, first time managers, who find and struggle with that decision point of, how much do I trust? How much do I let go? I don’t know if I’m going to see the caliber of the work that’s there. I mean, what advice would you have for folks in that situation who feel like they’re not sure if they’re ready to give that space? What would you say to that?

Rob: Yeah. I think that “trust but verify” is kind of what I start with, with people. So basically trust them to make the right call and see if they did, and over time you will learn to trust them more, and if they’re doing well, and if they’re not, then they’re probably not right for the role. I think that’s a big thing, right? It’s the kind of fire fast type thing, and in our world of start ups, when every person counts and you have a team of five or a team of seven, everyone needs to be high achieving.

And so I think when a new person would start, it was a slow, kind of a slow trust building in both directions to be honest, and coming back to your original question about leadership, that’s probably the one thing … you didn’t ask this.

But if I were to think, what is the one thing as a leader that is my job to do, and it’s instill trust in both directions. That’s what I strive for. And that ultimately leads to loyalty. I used to say it’s instill loyalty, but I realize trust comes first.

Claire: Talk to me about the difference. I’m so curious. I’m with you. I want to hear more.

Rob: Trust is just a matter of like, from my perspective as a leader, it’s like “I’m going to give you stuff or I’m going to help you figure out what to do, and I’m going to trust that you’re going to do the best you can and you’re going to come to me when you have questions, and you’re going to deliver a good product.” Trust in the other direction, to me, from my colleague, I believe is that I have your back in every situation. That when a customer screams at you on the phone, that that customer … I either have a conversation or I fire the customer, that I do not let my people get abused. And I’ve done that many times. Email and all that kind of stuff.

That I have your back when the database goes down on a weekday, I don’t just push the developer or the DBA to do it, that I’m actually sitting there as well trying to figure stuff out. That doesn’t scale when you’re at 50 people, but when you’re at five, yes. You trust that I essentially have your back, and over time. So trust is something that you can develop by showing up and by doing what I was talking about. And then I think loyalty develops with trust over time, and loyalty becomes less of “I know you’re going to be there,” and more of “I want to have your back as well,” if that makes sense.

It’s a mutual feeling of “I’m willing to take a …” either of us are willing to take a figurative bullet in business to be able to support you. And that may mean “Boy, I’m going to work this weekend even though you didn’t ask,” or “I’m going to work this weekend and not resent it because you did ask and I know that you don’t do this often, and I know that you need this,” or whatever it is. You know, we didn’t work a lot of weekends, but those are examples, right? It’s like “I’m willing to go the extra mile for you both as the founder and as the person, the developer or the customer success person.”

Claire: Absolutely. Yeah, no, I love that you emphasize that. It’s one of the main roles of the leader to instill trust, because I couldn’t agree more in many ways. Trust, it’s the oil of the machine, right? Nothing functions without that sense of trust, and you’ve got my back, I’ve got yours. And that when you argue we have our best intentions in mind. I’m not trying to screw you over, I’m not trying to take credit for something, and I think as a leader, again, our mental models around what leadership is, is about decisions, it’s about vision, it’s about charisma. Trust doesn’t get brought up very often, so I really appreciate you sharing that.

Rob: Yup. For sure.

Claire: Well hey Rob, thank you so much again for your time today. It’s been a blast to get to talk to you.

Rob: Absolutely. I enjoyed it.

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Watch our lessons for leaders: The Heartbeat Interview ❤️ with David Cancel, CEO of Drift (with…

Having started 5 previous companies and now running Drift with 130 people, David talks about redefining leadership as “pruning”, the power of one-on-ones, and the importance of “no consensus” in teams.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed David Cancel, CEO of Drift. Watch & read what he has to say here…

Claire: Hi, everyone. I’m Claire Lew and I’m the CEO of Know Your Company. Today we have a super special guest with us. We have David Cancel who is the CEO of Drift, this incredible sales conversational marketing platform that I believe has over 100,000 customers. Just has seen a ton of success. David is just a really amazing entrepreneur having started I believe I was reading five companies before he was formally the chief product officer at Hubspot. When it comes to talking about leadership we are so excited to have you. Thanks for being here.

David: Thanks for having me, Claire. I’m a big fan of the newsletter. Everyone here should be subscribing if they’re not.

Claire: Thank you.

David: It’s amazing. Thank you.

Claire: All right. Well, you heard it from David. I did not pay him to say that. Do it if you were not subscribed.

David: I’m also a subscriber to your app as well. I check The Watercooler every day.

Claire: Awesome. Yes. Love it. Thanks. Thanks for the plug there too. We have an online community for leaders called The Watercooler. David, that’s awesome that you’re a part of it. Well, you know the drill. You know what the question is coming up but I’m going to pose it your way. The question I’ve been asking all these leaders lately is: “What’s something that you wish you would have learned earlier as a leader?”

David: So many things. I think the thing I think about the most … There’s so many. The list is long. I should do a long blog post or something about this but the biggest one I think now is that it’s 99% people and 1% everything else.

What I mean by that is having spent my first half of my career focused on everything else, which is like building the software, building marketing, sales, this, that. All the stuff that we actually spend all our time reading and doing all day that was the 1% of it. The real thing is it’s 99% people. Those people being inside your company and those people being your customers and it’s all that.

Once you look at it from that lens then you think, “Well, those problems are pretty well-known” and it leads you to a whole different discovery in terms of reading, in terms of understanding about just how to communicate and how to talk to people.

Claire: Absolutely. Was there anything across your career like a moment you can nail down or look back to where that shift happened? Or was it a gradual process?

David: Yeah. I think it was gradual in that it took a long time.

I think what happened was you fail or you feel the pain, I should say, you feel pain enough times that you finally wisen up. Mother Nature is going to teach you the hard way or the easy way and I was choosing the hard way.

Where I would hit this is at a certain scaling point there’s always these magical scaling moments in companies that make no sense when you get beyond 10 and 50 and 100 then everything starts to break. I just kept going back to focusing in on the stuff that I thought was important but all the real problems and all the things stopping the company were all of these people issues inside, outside the building.

They weren’t the technical things. They weren’t go-to-market. They weren’t the technology. They weren’t the stack. They weren’t any of that stuff. It was really the people.

Claire: Absolutely. What would you say is the biggest people issue, if you had to choose? What do you feel like is one of the most challenging? I know, take your pick, right?

David: Yeah. I think basically it’s the communication. It’s the aspect of communication is we don’t really understand that everyone is slightly different or wildly different and that they need to be communicated to in different ways and absorb information and communication in different ways.

I think we all know that on the surface. Everyone would say, “Yeah. Yeah. That’s obvious. Yeah, I know that. I know that.” Then when we go and turn around and try to communicate to someone we communicate to them in the way that we want to be communicated to. It took me I’d say back in 2007, 2006, I had a company called Compete and we were just getting acquired. That was in 2007. I remember the dates.

Someone on the team, our VP of marketing at the time, wanted everyone to take a Myers-Briggs test. I was the CTO, I was engineer background, I thought it was the dumbest thing ever. I hated it. We were probably 150 or so people and I think I was number 150th to take it because I was just silent protest.

I took it and now it’s all I talk about is personalities and this and that. It was a discovery for me because not really in what it told me about myself because most of us kind of know a lot of that but the fact that everyone was so different and just looking at them and just trying to understand them just logically of like, “Oh, this is why when I say X, Y, Z in a certain way they’re not really getting it.” It was just this big light bulb moment from a very simple test that anyone can take online. Simple personality kind of assessment.

Claire: Yes. What are you, by the way, for the Myers-Briggs?

David: I am INTJ.

Claire: Ah, amazing. You know what’s crazy?

David: Yeah. I am INTJ.

Claire: Yeah. As am I, by the way. We are like 1% or 2% of the population, right?

David: Oh, really?

Claire: Yes. I know. I was about to say that’s super rare. No, but I find … First of all, I think that’s absolutely hilarious because I think there’s a healthy, natural skepticism around personality tests. I think we all like to think that we’re special or we all like to think that everyone is kind of like us. It’s usually one of the two or sometimes even a mix.

Right now I guess with your team how do you, as you lead Drift … Remind me how many employees that you are at today?

David: We’re 130 some odd. 130-ish. Yeah.

Claire: Excellent. 130 some people. How do you think about very, perhaps a little bit more tactically with 130 people, communicating in a way where you’ve got 130 people who are all over that Myers-Briggs test results, right? You’ve got INTJs, you’ve got ENFPs. How do you think about in your role as the CEO 130 people? Everyone needs a different communication style. What do you do in that situation?

David: I think one thing that I discovered over the time was that the most scalable thing in terms of keeping all of this working as teams were scaling here and then previous companies was actually the one on one. The one on one, which inherently seems like the least scalable thing possible and is the first thing that everyone pushes aside because they don’t have time for that was actually the key to actually scaling teams and helping make them effective.

In that context, the one on ones, we use a different set of personality tests but we talk a lot about Myers-Briggs and everyone knows that in a joking and posts their stuff and everybody wants to know what they are. Then we use something called Predictive Index, which is another flavor in this world. We use that in the hiring profile but as well as post-hiring to bring up these areas.

People are using this all the time internally even in their one on ones, kind of ongoing, and reminding themselves about it, “Well, this is how we communicate to Emily and Claire likes to be communicated this way so I need to tailor my approach.” It’s an active thing.

I kind of think about most of this stuff as English gardening. If you want an English garden most of the work is actually the pruning and the taking care of. It’s not the planting, it’s not the plant selection. It’s this constant pruning. The day that you stop pruning is the day that the garden is full of weeds and overrun.

Claire: Yes. I love that analogy. I also love that analogy just in the sense that it’s this idea of almost micro choices and actions that actually build a successful team. I think what a lot of people think about leadership, at least in how our society has thought of it, is it’s bold action. It’s big steps. It’s crazy decisions in moments of crisis and that’s what defines us as leaders.

Your take and what I’m inferring here is it’s actually the pruning. It’s the small day to day actions. It’s things you don’t say and do say in those one on one conversations. I think that’s incredibly valuable for the people listening. I guess … Go for it.

David: I think just to pull on that thread there I think that I take it to the extreme. I think it’s never the case that it’s these big bold actions. That’s a Hollywood myth. Now I’ve been doing this long enough that I’ve known tens of thousands of entrepreneurs and leaders. That has never been the case. That is a make-believe story that we tell ourselves and then we feel anxiety when leadership doesn’t look like that.

It’s not like that. It’s really a game of inches. It’s just like these micro little things and if you do them over time and long enough then you wake up one day and it’s magically this great result. It’s so weird to me that for whatever reason in leadership, especially in this time, we think it’s these big bold actions because it’s never been the case.

If you look at anything else in life it’s never worked that way. There is no this big bang thing and then I’m an Olympian athlete because I discovered some magic secret. It was starting at five years old and training for 10 years and then finding this overnight success.

Claire: Absolutely. Yeah, it’s that athlete that stays 30 minutes after practice but they do that every day for 12 years. That’s what separates those super athletes from the rest of us.

What would you say, David, are some of the other micro actions? Aside from communication and one on ones but other small nuances that you feel like most leaders don’t take the time to make time for or they overlook. What are some things that we should be considering?

David: Yeah. To me, it all comes back to the people stuff. It’s those one on ones. It’s the spending time in the hiring practice. We’re 130 right now and we are going to be around 200, add about 100 people this year, by the end of this year, to the team so we’ll be about 220, 230. I’m still involved in every one of those interviews.

Claire: Really?

David: Yeah. I’m at the end of the chain so it’s been very well-filtered by then so I’m not taking the bulk of that but still it’s 100 people that I’m going to talk to. I find the way to make time, even if it’s a 10 minute call, with those people because it’s a super important part of the process. I think that’s one of the first things that we’re like, “Oh, we’re 50 people now. I shouldn’t be in the interview process.”

Like, no. You should be in the interview process for as long as possible. I’m going to try and push that as far as possible and I think that’s important. My co-founder is the same. He’s involved in the process. If I’m not there he’s there or someone else on the team jumps in as well. It’s a super important thing. I would not give that up for anything because a lot of it is that and then a lot of it is the one on one and then the other stuff takes care of itself.

Claire: Definitely. I think some CEOs that are probably running smaller companies are thinking, “Oh, shoot. Oh my gosh. Maybe I got to involve myself in that.” David, what else would you say then … You said you had a big list of stuff so other than the people or the communication issues, anything else that … Here’s the thing. You’ve sat on numerous boards. You’ve mentored so many entrepreneurs over the years. Any parting words or advice for any aspiring leader or current leader who feels like they’re just struggling right now?

David: Yeah. I’d say we’ve all been there. One thing I would say is basically I think about this triangle and I think there’s three things that matter when it comes to your business. One is the market that you’re in. Two is people. Three is your product or solution or your service or what have you.

I’m most comfortable when I come from the product side of things. That’s where I come from. I kind of organize them first as market and then there’s a big gap, and then it’s like team — people — and then there’s product is third.

I always think about it in that order now but for the first half of my career I thought about it like most entrepreneurs do, which is the other way around, which is like it’s all about the product, it’s all around the service. No one ever thinks about the market. Like the market will will that to happen somehow.

Claire: Yeah, exactly.

David: Then they kind of think about the people a little bit. It’s kind of the opposite. It’s like big markets that are changing that allow you to relook at them or allow you to create a niche within them. Think a lot about that. Think a lot about the team. Those are the two big levers.

Then the product, we’ve all seen many examples. Not to say that we should aim for a mediocre product but great markets with great teams they can be mediocre products or not as good of a product that you can create that can own that market because those two things are true.

For us, engineers or geeks or what have you, we like to think about all the product, really the people, and that market that you’re in. That’s my advice. Really take a look at those two things.

Claire: I love that. I think what that speaks to is I think our desire as entrepreneurs, as leaders, to control. The product we can control it. Absolutely. We can build it. We can write about it. We can design it. It’s within our control. People, oh my God, no. There’s no way we can control in terms of people. Market? Forget about it. That is out of our control so we don’t spend the time.

David: I think you nailed it.

Claire: Yeah. As humans, that’s our natural tendency is we love to create any sort of semblance of control. That’s why we like to plan. I’m a big planner. I’ve noticed this even in myself as a leader. It’s like, Claire, you’re trying to create this plan because you’re trying to control for something that honestly you cannot control for.

David: Can’t control.

Claire: Right. It’s great to come up with those contingency … I think I love that share of focus and realizing that just because you can’t control it doesn’t mean you shouldn’t be spending the time and energy to think about it. Thanks for that, David.

One other thing that actually just came to mind. I was reading something on The Drift blog post recently. You had written a little bit about Peter Drucker, who is a seminal author of management. Love Peter Drucker. Who doesn’t, right?

David: Yes.

Claire: One of the things that you talked about that he talks about and I absolutely loved was this idea of no consensus in leadership. I thought it was really counterintuitive. Yeah, I would love to actually talk a little bit about that with some of our viewers here. Tell us a little bit about what no consensus is and what you mean by that and why you were so passionate about this idea in leadership.

David: One, I love Peter Drucker and we read a lot of Peter Drucker here. I’m about going back to the greats. You can skip most business books and go to Peter Drucker because they’re all derivative of him.

Claire: Yup. I agree.

David: That you read out there today. That’s where I would start. For us, no consensus, that idea really started with me with probably a decade ago, or maybe a little more, probably 15 years ago. Seth Godin who is another great writer, one of the marketing staff, had really wrote about picking an edge. What he would say is you’ve got to pick an extreme.

You’ve got to pick an edge. You can’t be in the middle. Then what I learned on my own after having that in my mind was that in creating a company the worst thing that you wanted was indifference. That’s what entrepreneurs battle in terms of creating a product is indifference.

It’s okay to have people love your product. That’s awesome. It’s also okay for people to hate your product because you can take someone who hates your product, who has an emotional connection to it, and move them closer to … You can move them to be fans. You can almost never move someone who is indifferent about something to be a fan.

Anyway, I had been thinking about that for a long time. One of our values here, we have eight, is no consensus. Consensus is the norm. We all regress to this idea of consensus within the company of, “Let’s all vote for something. Let’s hold hands. Let’s not be offensive. Let’s not take an edge.” I was all about picking an edge because that’s where I think the great things are created and consensus by definition is averaging down to the least offensive, least controversial thing, which is just going to lead you into the center of indifference. You’re just going to create something that nobody cares about, even the people that are creating it.

For us, it’s about picking an edge, going out there, getting a reaction from that even if it’s sometimes not the reaction that you wanted. Like people don’t love it but at least you can work from that because you’ve actually hit on something that they are connected to.

Claire: Absolutely. I find this concept so fascinating because I think a lot of entrepreneurs would agree and for folks who are starting successful businesses they reflect on their own product and they go, “Oh, we are doing well because we’ve picked an edge.” I think the tension in this concept of no consensus happens when we think internally with our teams about collaborating and moving forward.

In so many teams and CEOs that we’ve worked with there’s always this fascinating dynamic and conflict between how do you pick that edge but at the same time get people on your team not to kill each other and be bitter about the fact that it’s not their idea, it’s not maybe their edge?

David: You know how I do that?

Claire: Yeah. How do you negotiate that? For folks who are like, “But David, you can’t collaborate. How do you make decisions if you’re always picking the edge? Aren’t people going to get pissed off and leave?” Yeah. I’d love to hear your thoughts on that.

David: I stumbled on the answer back at Performable, which is like two companies ago, by accident. The answer that we’ve been using since then is this idea to create this customer-centric approach to building anything. We’ve taken it so far adrift that everyone and this is a kind of daily mantra here is that we tell everyone, including ourselves, that your idea and my idea is wrong. 100%.

The only thing we know for sure is that whatever idea we have is wrong. What we need to figure out now is we need to get out and work with our customers to figure out how wrong. It might be 5% off. It always is. It’s never you just create something and divine inspiration and then that’s the thing and it never changes. There’s always going to be a tweak to it.

Or it could be 100% off. It’s usually somewhere in between those two extremes. Why not get out there? Work with our customers from the very beginning to figure out how off we are. What we’re trying to do by doing that is to break down our collective egos, our personal and collective egos, and get out there and get over this part of, “Well, we can’t collaborate. We can’t do this stuff because we all are defaulted to say …”

Back to what Peter Drucker would say, the only goal of business is to serve a customer, right? We’re only here to serve. It doesn’t matter what Claire’s idea is or my idea or this person’s idea. What matters is what does the customer need? How do we best serve that?

Claire: Absolutely.

David: The only one who can tell us that is that customer. Not us.

Claire: Absolutely.

David: We’re never the customer.

Claire: I love that approach in, like you were saying, taking the ego, the personal or collective ego, out of it because I think that is …

David: It’s hard.

Claire: It’s so hard. I think it’s a huge reason for why a lot of decisions or a lot of progress isn’t made. I think helping to depersonalize any sort of potential source of conflict is huge. Then something interesting that I’d love to get your thoughts on is one approach as well when you think about consensus and collaboration or how do you build consensus when there’s conflict, is this idea that, yes, we’re all trying to serve the customer but also we can agree to move forward but not even have to agree on the same things.

I might move forward because I feel like I want to give this idea a shot and another person might move forward because, “No, this is actually going to be the thing that really helps us win as a company”. Whatever it is. We can move forward for different reasons and everyone actually doesn’t even have to move forward for the same reason as long as we can move forward.

Just accepting that there’s some plurality in that decision making process when you’re trying to find that edge. I could not agree more with you and I think it is such a hard and messy thing in practice. It really is. At least from what I’ve observed. Yeah.

David: This is why it’s all about people. Back to the beginning. It’s 99% people. It’s this. It’s like the ego stuff is a daily battle. In terms of pruning that’s mostly pruning all day. Including myself. Including everyone in the company. No one is immune from this.

I’d say at the beginning of this year I sent out a letter to the team that I wrote up, like a shareholder’s style of a letter, and I looked back at all the great stuff. It was an amazing year. I look back and I say, “Okay, let’s talk about the top five mistakes that I think we made as a team.”

I traced back and I said, “I think every single one of these mistakes” and I highlighted how, “Were due to ego.” Every single time we made a mistake it was due to our collective ego.

I traced back and I said, “I think every single one of these mistakes” and I highlighted how, “Were due to ego.” Every single time we made a mistake it was due to our collective ego.

What I’m trying to point out there is we made these mistakes. We don’t need to make these mistakes and we didn’t need to make any of the mistakes we did if we didn’t let our egos get in the way. How do we get better so that we don’t let our ego get in the way in 2018?

Claire: Absolutely. I think on that note that is a beautiful reflection that I’m going to be taking away from this interview. That’s for sure. I think for everyone watching there’s so much wisdom that you shared, David. Thank you so much for your time. This has been a blast.

David: Thank you so much for having me, Claire. I’m a big fan. Everyone sign up for The Watercooler.

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