Watch our lessons for leaders: The Heartbeat Interview ❤️ with Joel Gascoigne, CEO + Co-Founder of Buffer

Running a $19MM+ remote company with 82 employees, serving millions of people, Joel shares his greatest leadership lesson.



Every few weeks as part of The Heartbeat, I asks one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interviewed Joel Gascoigne, CEO and Co-Founder of Buffer.

Claire: Hi everyone. I’m Claire Lew, and I’m the CEO of Know Your Team, and today I have got a brilliant guest on The Heartbeat. I have Joel Gascoigne, who is the CEO and Founder of Buffer, the social media platform tool that hundreds of thousands of people use all over the world, including us here at Know Your Team.

Claire: Hi everyone. I’m Claire Lew, and I’m the CEO of Know Your Team, and today I have got a brilliant guest on The Heartbeat. I have Joel Gascoigne, who is the CEO and Founder of Buffer, the social media platform tool that hundreds of thousands of people use all over the world, including us here at Know Your Team.

Joel is someone who I have really respected and looked up to for not only the tremendous success in building a company that does over $19MM annually in revenue, has 82 employees, is remote first, but just very much in the way you’ve been I would say thoughtful and radically transparent in how you’ve run the company, Joel, and I think folks who know you and follow Buffer are always pleasantly shocked by that transparency. So, excited to open the book even more today and ask you this one question about leadership.

Joel: Yeah. Thanks Claire. I’m really excited to chat. Been following everything you’ve done for a long time, and these interviews I feel are super valuable, and all the content that you’ve put out there as well. Yeah, I hear about Know Your Team and you from people in my team, like all the time as well, and how useful this information is. Thanks for having me. I’m excited to chat.

Claire: Thank you. Awesome. Well, okay, Joel. Here’s the question that I’ve been asking leaders that I admire, and it’s what one thing that you wish you would have learned earlier as a leader?

Joel: It’s a big question. I feel like there’s a couple of things that come to my mind. It feels hard to maybe narrow it down, but I’ll start with one and then we can potentially…

Claire: We can talk about them all, as well.

Joel: … touch on the others. Okay. Cool. I think the first one for me would probably be that leadership is individual in some ways, in the sense that you can shape it to be the right thing for you, that fits like a glove for you. I feel like it’s easy to go out there and read about what you should do as a leader, this, and this, and this.

But I think one key thing that I wish I’d known earlier is maybe to also know that it’s important to look in myself and reflect deeply inside, and know what is the right style or approach for being a leader, being a manager, for the direction for the company, and all those types of things. I think that’s probably the key thing that comes to mind with that question, and it’s a very delicate thing, right?

Claire: Yes.

Joel: Because there’s a lot of things that you can improve and there’s definitely great information out there. It’s just also shaping that to be the right direction for you to go, or the right way to improve yourself in order to get good results, but also feel really great about where you’re going, and taking things as well.

Claire: Absolutely.

Joel: I don’t know if that makes sense.

Claire: It makes total sense. Now, I’m over here nodding, because I think there is such a pervasive undercurrent, even in our culture, about the archetypes of what a leader is, what they say, how they act, and it’s refreshing to hear that you wish that a lot of that doesn’t necessarily need to be listened to or paid attention to. I’m curious, Joel, when did that realization happen for you? Was it a conversation? Was it something that happened in the company? Was it a more recent realization, or was it something earlier when you were first starting Buffer and building the team out that you noticed?

Joel: I’d say it’s probably come up multiple times, and I think it’s maybe a few years in to Buffer probably. For context for people, I’ve been running Buffer for eight years now, so it’s over eight years since I started it. I think it’s also one of those things for me where maybe it’s related to my own personality or things I know about myself, where it’s easy for me to, I think self-confidence is an important thing as a leader as well, and having that conviction.

Depending on what your natural leaning in, for me I think I can end up doubting myself more than I maybe should.

I think that’s where there’s been times along the way, I think generally with Buffer, we’ve also done things our own way. I guess that’s one of the things people would say about us, which I’m proud of, but I think even though people would from a high level say that, I feel personally for me, there’s been points where I’ve still deviated from what is maybe the best path for Buffer, that aligns with myself and what will be fulfilling for me over time, and also maximize the chances that I can make Buffer a success, because it aligns with my own life values and philosophies and things.

Joel: There’s definitely been moments where I feel like I’ve been a bit offtrack, all along the way probably.

Claire: Yeah. I can totally, again, I’m nodding my head over here, Joel. I am curious, and I’m sure folks who are listening to this, what have been those offtrack moments? Or is there one that maybe comes to mind?

Joel: Yeah, I think one is probably getting … One clear one is getting too much onto the growth track of the company, onto maybe the VC. Growing for the pure reason of growing. I think there’s a lot out there that says the definition of a startup is growth, or it’s like a lot of these things out there. I just realized for me that doesn’t align, that doesn’t resonate for me, but I think the more you consume and take in and read of things, if you start reading too many of those things like that then it can get in your head and then you can convince yourself that you need to be on that side of just pushing for that.

That’s one example. I think the thing that helped me get out of it a little bit is reading or watching presentations of things from a wide range of different types of founders or companies, and at least for me, what resonates often is more the non-traditional approaches to building companies, and that’s I felt, has given me a nice balance. So then I can, I feel like the default is this very clear track and so for me, just to make sure I can seek out and find these other ways of building companies, feels like it gives me this balanced viewpoint, but then I can decide, “Okay, what’s the right thing above that?”

Maybe that’s also another thing I wish I’d known, is like that:

It’s great to have conflicting advice, because then you have to make your own decision. Then then you have to look within yourself and decide what is the right thing for this company, for the culture, personally for yourself, as well.

Claire: Absolutely. I love that. Insight is counterintuitive as it is, because we often as leaders, gather expert opinions. It’s either to confirm or disavow something in our head that we are learning towards. I’ve noticed this in myself that to your point, it’s very easy also to seek out advice that’s going to also affirm each other. It’s very confusing when the advice conflicts. You’re like, “Wait, I’m trying to solve a math a problem” and the elements are all there.

Joel: It seems like it’s not helpful, but it really is, I think.

Claire: Right. I love this suggestion to actually proactively seek out advice that goes against each other. I love that. I think for folks listening, one thing that they might be curious, that I’m curious about, is the discernment of that advice when it conflicts, and I’ve had this conversation with a lot of different CEOs and founders. Is the default right answer to always trust your gut in that situation when the conflicting advice, or when the advice conflicts?

Or, how do you choose which decision to make? How do you carve your own path when you’re given all the options? What do you as Joel, how do you map that out for yourself? I know it’s very context dependent. It really depends on the situation that you’re faced with, but broadly speaking.

Joel: I think this is a really good question because I think it almost goes back to my first answer which is leadership is individual, in the sense of what’s your style? Because if you’re asking me how would I figure that out, I learned time for myself, that I need to go away and have space to reflect on things. I want to go in and hear these conflicting pieces of advice, two different people, or more different people, groups of people, and whatever it might be.

Whether it’s leadership team or advisors or people, and then for me, at least for me personally, the state I’m in when I’ve just heard it is that it’s kind of like a cloudy glass of water. It’s just all shaken around, and I personally have to go away and let that settle a little bit, have my own space. I’ve learned for me as a leader, that I really try to avoid making decisions in that moment, in a group discussion, or things like that, which can be a bit unusual because a lot of teams, a lot of companies I think will go into a meeting, want to discuss something, and come away with a decision, but for me, if I’m the one that is making the decision, I’ll often, does take me a while to figure out.

But I’ll now just say I’m not in the right state of mind to make this call right now, I’m going to go away and think about it, just overnight. It might not take long. It might have taken an hour from being away from that, and then this cloudy glass of water settles, and then I have this clear mind on it. Usually for me, that’s when I have the epiphany of, “This is the right thing.”

I wouldn’t say it always needs to be good. It might be that I go away and get a spreadsheet going and try and figure some stuff out or that kind of thing. It’s interesting because when … My co-founder left the company about two years ago. When we worked together intensely, in some of the key earlier years of Buffer, he’s the opposite. He is more someone that has their best clarity of thought and ideas and things in the discussion, and he wanted to make those calls in that moment a lot of times.

It took us a while to figure out that, “Okay, we just have different approaches here and that’s fine, and we’ll find a way to make it work.” We ended up starting to have two meetings instead of one for things, so we’ll have one, bounce ideas around, shake it all up, “That’s great, we need to do that” and then go away, have a gap between them and then come back. I’ll usually, when we started doing that effectively, we found that I would often come back with some new idea or connecting dots in different ways, or I’ve had this new thought, that we just wouldn’t have had otherwise if we just made the call and moved on.

Yeah, maybe that’s an example in itself of like you need to know yourself a little bit as a leader, maybe you might love those heated discussions and making a call right there and then.

Claire: Absolutely. No Joel, so I love, I so appreciate that response because it shows your willingness to even expand that viewpoint of having conflicting advice, even to your approaches, right? You like an integrated approach, you like a different approach. You liked the fact that your co-founder had a different way of making decisions, more in the moment, you needed to take some more space, and I think it’s so interesting how comfortable you are in having conflicting styles to be working and coexisting in the same space.

I also think, by the way, that I personally have found that there’s this phrase that muddy water clears when you leave it alone. The more you stir it, the foggier that it gets, and I believe the mind works similarly around decisions. Well, at least for me. It sounds like for your co-founder, that wasn’t the case.

Joel: Yeah, maybe not to everyone. But certainly for me. Or it might be that for him, he needs to clear his mind regularly, like as a general practice, but in the moment, maybe he needs to do that regularly in order to be in the good state for those meetings, or that kind of thing. Yeah, he would have some of his best ideas in a very collaborative setting, whereas for me, I would maybe have a great discussion but over time, that would actually drain me and then it’s when I do then let myself go away and just reflect by myself that I would have some of the best ideas, and come after the discussions.

Claire: I also think that your description of your style and your former co-founder’s style goes to show your point again, of the individual nature of leadership. I’m wondering for you Joel, what has really influenced your own individual take on leadership? We are born into this world without being completely untouched. All of us, each of us, are shaped and influenced by different things. I’m curious for you, what’s most influenced your style of leadership, or your views on leadership?

Joel: Yeah. That’s a really good question. I think there’s many different influences, but it probably is these companies going their own direction and just dig in and read about them. I think Basecamp would be an example of something like that. MailChimp maybe would be another one. I think there’s also more beyond the pure tech sphere, I think there’s also companies such as Semco.

Claire: Of course.

Joel: I’ve read both of Ricardo Semler’s books and massively influenced by those.

 Zappos maybe another one. Recently I’ve been really getting interested by more cooperative models for companies, or employee ownership models for companies as well. Companies like Organic Valley which is actually a co-op in the US, and then there’s a company called John Lewis in the UK, and I’m from the UK so that’s one that’s been interesting to come back, just in the last year or two.

It’s a company that has a very, it’s very well regarded. It’s very respected in the UK and it’s been running a very long time. It’s a big department store, but every single employee is technically a partner and actually owns part of the company, and then they do a profit share at the end of each year. They’re famous for based on the profits of the year, they will determine what percentage of salary, what percentage will be a profit share.

They’ve been through lots of ups and downs so they’ve had some years where it’s not been a great outcome, but yeah, just digging into their model has been fascinating as well. They have a lot of details online.

Claire: Totally. I similarly think that looking at stories, just what’s been done, there’s so many answers and so many sources of inspiration there. One thing that, as I mentioned in the introduction, Joel, that you are known for and that Buffer is known for is transparency, and revealing, I mean actually prior to this interview, I found on Baremetrics that I could literally look up your annual run rate, and look up what your percentage of churn you have every month.

It’s quite unconventional. Well, it’s conventional and unconventional because what I will say, as I feel like it is extremely trendy these days to say that you are transparent as a leader, and to say that your company is open. It’s become in my opinion, almost a little cliché. That’s one I think arc that we’re seeing. The other arc that I think we see is almost a backlash to that, so I’m sure you get this all the time about, “That would never work in my company. Open book financials is a disaster. Saying what everyone makes in terms of salary.”

I just really want to dive into first of all, where does this urge to be so transparent come from? Let’s start there. Why do you do it, Joel? why?

Joel: It’s a good question.

I feel like there must be several different things that have contributed to that in my childhood, or whatever it might be. It’s also, I think it’s worth noting that it’s one of those things that it’s totally possible to do in a small way, and then to build up, and get further and further into it, and then feel like, “Wow, this is so great so we’re going to keep going here.”

I think that’s happened a little bit where it’s not necessarily the right off the bat, I was thinking eight years ago this is going to be this transparent and everything. But we’ve had so many great outcomes and impacts of that. There’s one experience I had when I was doing college, university in the UK, and afterwards, I was an intern, doing some work freelancing, and then afterwards I worked three days a week for them.

 I almost was going to work full time but I was wanting to do my own projects, so I managed to just work three days a week, but I was pretty involved with this company. I was working for them. They were a very small company, maybe 15–20 people. In the time I was there, essentially they went bankrupt towards the end of … I was doing contract work, but there was others who were employed and as things got worse and worse, everyone knew, but nothing was really being shared too much.

This is a 15–20 person company, and people just didn’t know what’s the actual situation, what’s really going on? For whatever reason, the owner, the CEO I guess, managing director they’re usually called in the UK, she must have felt like it was better to hold onto that information and take that burden completely on herself.

But the outcome was just so bad. It hurt so many people, a lot of people without pay for three to six months, and then just got nothing at the end of it. That’s one key experience that was maybe just a year or two before I started Buffer, which I think definitely had an impact, made me feel like I don’t know, I guess I reflected on and thought, “Well, if someone knew, maybe we could have all come together and tried to make this happen and turn it around.”

But no one even had that chance because no one really was given the full information. In a way, I think what I’ve done with Buffer, a lot of times it’s just go to the other extreme which is everyone should have … I’ve also heard this phrase or this quote which is, “If you want people to be able to make the same decisions that you would make, then they need to have the same information that you have.” Generally you’re going out there, you’re trying to make people entrust you, that you can actually do things better than you, so how on Earth can they do that if they don’t have the same information?

That makes it sounds very obvious and easy and clear, and like you say, it’s a bit of a cliché maybe, transparency, but I think what I’m really talking about is actually following through with that, going all the way and regularly sharing the bank balance with the team, and all the financials. 

We decided to also share a lot of that publicly as well, but it just keeps us accountable, I think. Actually, it’s quite liberating for me. It actually lifts a few things off my shoulders. 

I think founders and leaders and CEOs, it’s stressful enough and I’ve had some real low points on the journey. I think it would have been even harder if we didn’t have this transparency.

Claire: I think that’s probably extremely surprising, I think, for me to hear that and for other folks to hear that, that you feel your job is easier, because you are pulling back and sharing the burden more. To your point, the managing director that you were mentioning, she didn’t want to share the state of the company because of fear, because of potential ramifications and backlash. It’s so interesting and admirable, Joel, and I think it probably says a lot about you personally, that your own reaction is actually quite different, that it actually relieves a lot of stress for people to know what you know. Yeah, go for it.

Joel: I wouldn’t say it’s easy.

Claire: Of course not.

Joel: And I think there’s still times where we’ve fallen short of that a little bit, but I still come away, even in those moments where we go through a really tough patch and I come away afterwards thinking, “Maybe I could have shared more.” A lot of times now it’s because we’ve made this commitment and I feel like I really want to stay true to it, transparency.

But it also, I’ll sometimes have the reflection and think, “It maybe could have been easier” or not necessarily easier, but a better outcome maybe for the team, for morale, or everything. ’Cause even if you get through it but you’ve not shared that with your team. The other thing is, I got a really great piece of advice from Tony Hsieh from Zappos one time, which was he talked about the importance of building resilience in your team.

I think there’s an interesting balance of you want to make sure people feel safe and comfortable and everything, but you also I think, it’s worthwhile including the team and exposing the team to some of the really tough decisions, even if maybe they’re not having to make those decisions, but just to transparently share them, and make them aware of the big choices going on right now.

I think that in itself is an act that can build resilience and help the team be able to handle more things that might be thrown our way as a company.

Claire: Totally. I feel as though the contrarian who’s watching this would say, “Joel, that’s great for your company, and Tony Hsieh gave you that advice, that’s great for Zappos, but for my company, my employees came to do a job, 9:00 to 5:00, there’s some folks who just choose to actually be an employee because they don’t want to have to deal with those issues. They don’t want to have to think about the possibility of laying off 10 people. They don’t want to have to make complex, high stakes decisions, based off what’s changing in the market.” What would you say to someone who feels as though they like the idea but the practicality to them is not quite there? What’s your response to that?


I feel like you’re treating people as kids with that view, because people have to make these somewhat challenging decisions all the time in their lives, and then we’re all coming together as a company. 

I think sometimes, especially as a company grows, and you have more hierarchy and bureaucracy and things, you end up really splitting off the different roles and having really a lot of specialization and things, it’s really easy for things to become siloed, and people on one side of the company to not have at all any of the information from the other side, or from the top and things.

But I think it’s a way, that to me is a way to make yourself feel okay about not sharing more and I just think, actually people can handle it. Like, we’re all adults here, we’re coming together, so I believe that, and I also believe people want it. It can be hard, but I think that’s where building resilience comes as well. You can start small, you can grow that and things, but yeah, I just think, I also think if you would go into any company and speak with someone that’s not in the leadership team in some way or something, someone that’s in a role in customer service or in engineering or whatever it might be, I think if you were to ask them, you would generally always find that there’s decisions being made and they don’t know why.

They don’t have the context and they’re questioning them, and then there’s resentment building up in the leadership team, and I think that’s one of the biggest challenges as a growing company, and we feel that a little bit. Now we have over 80 people and I think that’s going to be one of our biggest challenges, is how do we keep that trust in the leadership team, what we’re doing? That’s I think another fundamental belief I have, is that it’s really important to regularly communicate the why of decisions.

For me, anytime that a decision’s being made, my ideal scenario is that anyone can follow that back to understand why.

I often think about the sharing why is more important than sharing what. The direction is important for people to know where we’re going, but I almost focus on the why, which is like what are all the different pieces of context, information, data, everything, that’s in my head that’s led me to make this decision of company direction, or a specific decision on level of benefits we provide, or compensation, or whatever it might be?

I think it’s really important that people have that actually information and the context there, because to me, the ideal scenario I aim for is that people could actually come to that same decision themselves, or at least understand and agree, “Okay, this is all taken into considerations that have been made and this is the decision that we landed on.” Whereas I think in a lot of companies, you have decisions being made all the time, or policies put in place, and passed down, that eventually you get so far, so many layers of that, that at some point you have these things going on that people are asking, “Why? Why is this?” And you can’t answer it. It gets lost.

Claire: Absolutely. I’m going to make an assumption here, actually. I think everyone who’s watching this is also nodding their heads, going, “Joel, yes, totally with you. Transparency builds trust. People need the same information to make decisions. Yes, we shouldn’t treat our employees as kids,” right? I think people would nod their heads to that and people would nod their heads and go, “Absolutely. We need to communicate the why, we need to show the direction of the team” and so here’s the thing. Why don’t we do it as leaders then? Why is this so hard and what advice do you have, Joel, to actually put this stuff into practice?

I feel this is so true of most leadership concepts, which is it’s obvious when you read it or when someone tells you, but when you go to actually implement it, it’s so difficult. Talk to me about practically, what advice you have for folks who are going, “Okay, I want to start doing some of those things.” What tips or what thoughts do you have there for me?

Joel: Yeah, I think it’s really hard to do.

Claire: It’s so hard.

Joel: You can hear it in the theoretical sense, like we’re talking about it now. When it comes to the practice of it, it almost goes against human nature. It’s really hard to do it. 

Claire: How do you do it? How do you remind yourself and hold yourself? You alluded to this, accountable.

Joel: I think this might be one of those examples where it’s like go slow to go fast, where I think for me, I feel like I need to be going just that optimal pace myself with how much do I cram into my week that I’m doing. I need to have enough space that I can actually reflect on things and think, “How does it feel? Is the way we’re approaching this decision or this communication with the team, is it right?”

I think you need to fill that space for yourself, to be able to have the reflection and the realization of, “Oh, this is actually going against some of these concepts.” Then, I think you’ve got to make the time, which is the other thing that can be really challenging in a company that’s growing fast, or just has a lot going on. All small companies feel like really they could do with twice as many people as they have, or that kind of thing.

I think it’s hard to take the time to do some of these things, take the extra time to … It takes more time. It’s more work to be transparent, because you’re sharing the data, the numbers, and you’ve got to explain the context. It’s one of the things I love about transparency is that it forces us to do that. It’s not just about, “Now we’ll just throw out the salary numbers” because the fact that we’re sharing salary numbers with the whole team means now we’ve got to explain our process, our system to come up with salaries, everything, all of that context and it forces us to do that. But all of that takes a lot of time, and I think that’s maybe the other key part, is make time for it and start small.

You don’t have to feel really intimidated by the amount that maybe we do at Buffer. You can start small and just open up a little bit, or share a bit more of your financial results or numbers. Whatever it might be. Just look around, look at the things that you’re keeping private within one time, and within leadership team especially, and think, “Can you share that?”

Claire: Absolutely. I think what you’re describing about taking the time and carving out that time, it’s something that’s been echoed by Michael Lopp, who’s the VP of Engineering over at Slack. He talked about when I had him on the show, don’t be busy. You need the time to watch people, observe, have those conversations, and most importantly to think for yourself. I think time is huge. I love your point about starting small, and providing context also around transparency. Yeah, it’s funny, another guest we had, Des Traynor, one of the founders of Intercom, he talked about this too.

Transparency’s on a spectrum and you have to give context to it. It’s not just saying what someone’s salary numbers are, but being defensible, right?

Joel: Exactly.

Claire: And showing to your point, the why. One thing that I think I’ve found in myself and I’m curious if you would line up on this, or disagree, is I also think it requires actually a really strong internal compass and discipline, and level of rigor to hold yourself accountable to the things that you say you want your company to do, or you like. It’s a deliberate choice here that you’re making, Joel, to focus on the why and to be transparent.

Joel: Yeah, I think that’s true.

Claire: You can either like you said, you can easily come up with almost reverse justifications for being like, “Oh, we’re going to change our mind” or, “We don’t need to go as deep on the why on this.”

Joel: Yeah. I think that’s also where I would say find the thing that resonates for you and maybe go deeper on that. It might not be transparency or some of these things for other people. I feel lucky in some ways that I’ve found this thing that I do feel like I have this internal compass on, and I feel very strongly about, and it’s not been easy and it’s come with sacrifices I think along the way, and I’ve had a few people tell me that and say, “Wow, I don’t know if I could have stuck to it through that” or made that decision.

We bought out our investors recently. We turned down big acquisition offers, and a lot of it’s been related to these things we’ve been talking about, but I think that’s one of the things that makes the company special I feel like, and it’s one thing that’s a useful thing to do once in a while that I ended up doing, is once in a while just reflect on the trajectory you’re on right now.

If you follow that through, a year or two years, do you want to be part of that thing? Is that still exciting to you?

I did that a few years ago and I wasn’t too excited about … I felt like I could wake up one day and not feel so excited about being part of the company with that trajectory it was on. I think that’s a really useful exercise and just helps you maybe to determine what are those things that you feel strongly about, and that’s why I think it’s worthwhile finding your own path. Even if your own path happens to align with the path that is traditional out there, or whatever it might be, that’s great.

If it’s the one that you feel aligns for you as well, but I think that’s the thing that I’ve tried to step away, reflect on, and spend time thinking about, and just feeling really comfortable and happy and confident with, “This is the direction I want to take things.”

Claire: Absolutely. That is so encouraging, Joel to hear, and to your point, it only comes with time and with stepping away. Thank you. And speaking of time, thank you so much for your time on having this conversation. There’s so much that I learned, I know I’m going to rewatch this back, I’m sure take a bunch of notes. I know for everyone who’s watching as well, they learned a lot too, so thank you so much for being here, Joel.

Joel: Yeah. Thanks so much, Claire. It’s been a lot of fun to chat.

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

Building trust in teams: What and why?

How do you build trust in a team? First, let’s understand what trust really is and why it matters.

Who do you trust?

The first people who likely came to mind were your partner, your family, and your friends (hopefully). 

How about your boss? Your coworker? It’s harder to say. 

A 2016 study conducted by Edelman surveyed 33,000 people in 28 countries. From it, they discovered: One in three people don’t trust their employer. And only 24% of employees in this study believe their CEO exhibited highly ethical behavior.

In our own Know Your Team survey this past year of 597 managers and employees, we found that folks were slightly more trustful of one another: About 8% of employees said they rarely or never trust their manager. That’s almost 1 in 10 employees not trusting their manager. 

Why defining trust matters

Whether 1 in 3 employees or 1 in 10 employees don’t trust their managers – both are significant occurrences. Especially given the amount of time we interact with our coworkers, and the projects and outcomes that are on the line, it’s startling.

Are we really spending all this time with people we don’t trust? Should we be doing anything about this?

To answer those questions, we first have to define “trust” clearly. Misconstrue what trust actually is, and you spend time on the wrong things. Get it right, and building trust gets easier.

What trust is NOT:  Likability

We often equate trust with likability. We think, “This is a nice person” or “This is the kind of person I’d want to hang out with on weekends”… So we trust them. 

However, that’s only part of the equation. 

Consider someone in your company you don’t trust. You might like her. She’s affable, genuine and definitely tries her best. But trusting her with a high-profile project? You hesitate – she hasn’t shown the track record you need to feel confident. You don’t give her the big project because, honestly, you just don’t trust her enough.

So you if you want someone to trust you, it’s not enough that they like you. It’s not enough that they think you have good intentions. They’ve got to think you’re capable. They’ve got to think you have what it takes to prove something through. 

You might think someone is a good person – but you don’t trust them to actually get the work done. You need both.

This is an important distinction because many leaders accidentally optimize for likability as a means to build trust. They try to “be friends” with their direct reports, thinking it’ll mean their team will trust them more.

If we can internalize that trust is not likability, it causes us to not fall into the trap of trying to please everyone around us. If we want to build trust, there’s something deeper we have to access.

So then, if trust isn’t likability, what is it?

What trust IS: Intentions + Behavior

In a 1998 paper, Denise M. Rousseau suggested this definition of trust:  “A psychological state comprising the intention to accept vulnerability based upon positive expectations of the intentions or behavior of another.”

In short, trust is two things:  Intentions and Behavior. It’s people’s perception of who you are, and their expectation of what you can do. 

The 4 Cores

Stephen M.R. Covey defines trust in his popular book, “Speed of Trust,” similarly to Rousseau. To Covey, trust is the belief in who the person is, and a belief in their abilities – a person’s “Character” and their “Capabilities.” Covey then further breaks down trust into what he calls “Four Cores”:

  • Integrity – This means being honest, walking the talk, and being congruent with what you believe. You can’t trust someone unless you believe they have integrity. When someone is assessing your integrity, they’re wondering, “Do you have values I align with? Are you a good person?” 
  • Intent – This is your agenda or mission. Your team must trust your intent before they can trust you. A person sizing up your intent will wonder, “Are you thinking about yourself, or others, in this situation? Do you have the short-term, or the long-term in mind?”
  • Capabilities  – This is your talents, attitudes, skills, and knowledge. When someone is determining whether or not to trust you, they’ll consider, “Does this person have the expertise to do this job as well as they say they can?” Based on our survey, we found that both managers and employees most question their each others’ capabilities (26% of employees said this, and 36% of managers said this).
  • Results – This is your track record, your performance. You can’t be trusted unless you’ve shown results in some way that you can be trusted to follow-through. When you ponder about a coworker, “What has this person done that proves I can trust her?” you’re seeking results.

Warmth + Competence

Another related lens for understanding trust is described by organizational experts Amy J.C. Cuddy, Matthew Kohut, and John Neffinger. They revealed the two elements needed for a leader to be trusted were “Warmth” and “Competence” – with warmth needing to come first. 

According to their research, when you project strength too quickly, people have a harder time trusting you. They explain in Harvard Business Review, “Before people decide what they think of your message, they decide what they think of you.”

These perceptions of warmth and competence are powerful: “Insights from the field of psychology show that these two dimensions account for more than 90% of the variance in our positive or negative impressions we form of the people around us.”

How do you show warmth and competence? Cuddy and her research partners detail how warmth can mean positive body language, affirming words, generous actions, and even a smile. Competence can be projected similarly through body language (such as standing up straight), your past track record, and the actions you take going forward.

Like Covey, Cuddy’s research and explanation of the requirements for trust echo Rousseau’s definition of intention + behavior. Trust is all about who people think you are (warmth), and what they think you can do (competence).

Getting this distinction straight helps lay the groundwork for you to build trust in your team. You can now understand why someone might distrust you. Perhaps you haven’t defined your intent clearly enough. Perhaps it’s because of your past behavior. As a result, most importantly, you now can start to think how you can build trust in your team.

The clearer understanding we have of trust and what it really is, the clearer path we have to our teams trusting us more.

The Mindset Shift: How to become a good new manager

How to become be a good new manager? Of all the management advice for new managers, embrace this one, first.

Don’t be fooled: Becoming a manager for the first time is deceptively difficult.

No matter how many leadership books you’ve read or conversations you’ve had with mentors – the transition to becoming a manager is precarious.

Talk to any leader, and they’ll affirm this. “I was a terrible manager when I first started,” most will say. Myself included!

This is because the change required to be a good new manager isn’t apparent from the outside looking in. You’re not truly aware of the change that’s needed in the role, until you’re actually in the role.

So what change do you need to make as a new manager? From 15,000+ people we’ve surveyed through Know Your Team and thousands of conversations with managers in our online community, the #1 consistent insight folks have shared is this:

Becoming a new manager isn’t merely a change in what you do – it’s a change in how you think.

When you become a manager, your responsibilities change and your daily schedule changes. But it’s your mindset that changes the most.

The biggest change in thinking, as a new manager, is that your best work is not you doing your best work. Your best work is creating an environment for others to do their best work.

You don’t think about, “Am I moving fast enough?” Instead, you now contemplate, “Am I removing obstacles so my team can move fast enough?”

You don’t consider, “Do I know the answer to this?” Instead, you ask yourself, “What am I doing to help my team become experts and find the answer?”

Becoming a good manager starts with how you think, not what you do. Shift your mindset, and the actions follow.

This shift in mindset, while seemingly obvious, is both substantial and hard to internalize. What previously indicated “success” for you as an individual contributor doesn’t indicates success anymore.

No longer do you pat yourself on the back when someone says, “Great work” or “I love what you did here”. As a manager, the small bump of validation happens when someone says: “Now I understand,” “Thank you for listening,” or “I’m excited to work on this.” The small wins change when you’re a manager.

This shift doesn’t happen overnight. We have to disregard the prior experiences of we were rewarded for as an individual contributor. We have to reconfigure our default settings of behavior that got us to where we are now.

But if you can embrace this mindset shift as quickly as possible, your ability to become a good manager exponentially increases.

You don’t have to wait til you’re in the thick of everything, as a manager, to know what you must change.

Now you know: You must change your thinking, first.

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…

The most counterintuitive leadership tip? Leaders, stop doing what you’re good at.

Playing to your strengths as a leader doesn’t make you a good boss – in fact, it can make you a bad boss. Here’s why.

Of all the tips to be a good manager, “leaning into your strengths” has got to be one of the most frequently cited.

“Do what you’re good at. Focus on your strengths.” That’s the conventional advice we all receive. There’s no shortage of StrengthsFinders assessments and personality tests urging us to triangulate which strengths we should zoom in on.

However, I recently had a conversation with Peldi Guilizzoni, CEO of Balsamiq. His insight on this topic turned my head sideways… in a good way. Peldi asserted:

“Doing what you’re good at hurts the team.”

Huh? Let me explain.

Peldi admitted to me that he’s good at getting stuff done. He makes things happen. He thinks he’s killing it. But as a CEO, 10 years in, should he really the one doing all the doing?

After a decade running his business, Peldi noticed he’d created an environment where his coworkers were depending on him to get things done. If he takes a vacation – he leaves them hanging. If he has to be out for a week – they’re stuck.

Peldi conceded:

“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.”

Doing what he was good at was hurting his team, not helping.

I could relate.

I’m good at communicating. So I do it internally. A lot. I write-up about what we’re doing, why we’re doing it, a new approach I’m thinking about, a new concept we should try… But, when I take a step back, it’s a bit too much. We’re a tiny, two-person company. For our size, all that communicating is overkill. I could easily spend some of that same time somewhere else in the business and have it be more meaningful.

For both Peldi and I, our predisposition became a preoccupation. We’re good at it, so we automatically assumed it was good for our team.

Whenever you’re good at something, you don’t objectively assess its effectiveness as you should. You apply less of a discerning eye. You know you’re good at it, so you figure the more you do of it, the better.

But as with anything, repeated actions without rigorous judgment become lazy and reckless. And naturally, they have unintended consequences.

Now avoiding this pitfall is hard.

No one is going to stop you. Rarely do others have the temerity to stay, “What you’re good at is bad for the team.” Plus, doing what you’re good at is fun. It’s inherently satisfying to flex your strengths. Who wants to not feel that way?

So, you have to ask yourself: Are your actions feeding your team, or your ego?

Focus on what you’re good at, and the team never becomes good at it themselves. Focus on what you’re good at, and you never see things for what they really are.

Resist viewing your strengths as the only way to make the team strong. Resist falling in love with the short-term results of doing what feels good to be doing.

Pause. Don’t be so busy. Take stock. Why are you doing those things? Because you like doing them? Because you’re good at them? Or because it’s the best way to move the team forward?

Find someone who will tell you the truth. Your co-founder, your coworkers. Ask them if what you’re doing that you’re good at is really helping move the team forward.

This truth-seeking takes 10 minutes to do. Start today. And stop doing what you’re good at, all the time.

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

Big news: Know Your Company is now Know Your Team 🎉

After four years, we’re launching a new product, business model, and company name. Here’s why.

We’ve always been a bit weird.

We’re a two-person company serving 15,000+ people who use our product in over 25 countries. We’ve generated almost $2MM in revenue to date, have been profitable since Month 1, and every year since. We’ve never raised money from investors, or taken out a bank loan. (And, we started out as a tiny prototype that Basecamp spun-off.)

Today, we’re doing something weird, again.

We’re launching a new product, business model, and company name.

We’re now Know Your Team software that helps managers become better leaders. We give you educational guides, tools, and a community of support to help you avoid becoming a bad boss.

Know Your Team costs $65/month per manager (or $600/year).

You can check out the new Know Your Team here.

Here’s why we decided to make this change.

Quick background, first.

If we’ve never met before, hello! I’m Claire, CEO of Know Your Team. It’s nice to meet you, albeit virtually.

Our original software, Know Your Company, used to be focused on helping business owners with 25 to 75 employees get to know their company better. We charged $100 per person, one-time, for life.

We generated $1MM in cumulative revenue in a little over two years. We helped tens of thousands of people at companies like Airbnb, Medium, Kickstarter. And not just at tech companies, but law firms, marketing agencies, retail stores, and even a few churches.

When we surveyed customers, 94% of employees said Know Your Company helped them feel more connected to their coworkers, and 85% of CEOs said Know Your Company positively impacted their company culture.

Yet as 2017 was winding down, we noticed our sales becoming flat.

“What’s wrong?”

I remember thinking this around this same time, last year, in December.

As I reflected on 2017, I noticed three things:

  1. Our online community for leaders took off. We’d launched our Watercooler community in October 2017, to help managers learn from each other. More than 200 people signed up for it in the first month. (Today we have almost 1,000 members.)
  2. Our writing about leadership took off. The writing I’d been doing on our blog increased our organic traffic by 3X in a month’s time. It would go on to increase by 20X over the next six months.
  3. Our software sales went down. Our sales, however, did not increase. Not 20X. Not 3X. In fact, sales were fairly flat in 2017, if not dropping during some months.

Seeing the discrepancy between our audience and our sales, we scratched our heads.

Yes, Know Your Company was helpful as a piece of software. But for who?

When we got started back in 2014, we focused on selling to business owners. But by the end of 2017, our audience had evolved. After some digging, we learned that our 20X increase in traffic were mainly managers at companies of all sizes.

We had a mismatch. Our audience was managers, but our software was for business owners.

Our audience was asking the question, “How do I become a better leader?” But our software, Know Your Company, wasn’t answering that question.

In fact, no one was doing a good job of answering that question, “How do I become a better leader?”

Sure, you can read books, but they lack practical application. Trainings are expensive and one-time. And man, making mistakes and learning trial by fire is awfully painful.

I searched high and low for a good answer to, “How do I become a better leader?” I couldn’t find one. So we decided to build our own.

The result is Know Your Team.

Introducing Know Your Team: The new product.

To answer this question, “How do you become a better leader?” we re-imagined our product.

We pulled together research from working with 15,000+ people over the past four years, and discovered that the best leaders do three things exceptionally well:

  • Trust: If you don’t build rapport as a leader, nothing moves forward.
  • Honesty: If you don’t speak the truth to your team, problems fester.
  • Context: If you don’t get everyone on the same page, confusion sets in.

Because of this, we designed Know Your Team to help a leader develop these three skills of Trust, Honesty, and Context.

You can read more about our methodology here.

The best way to learn anything is to go do it. The second best way is to practice doing it. So with Know Your Team, we combined theory with practice. You can’t become a better manager by just reading books, or just by using software tools, alone. We built Know Your Team to include 3 complementary resources, to be used together:

  • Guides — Written guides on leadership, based on data, with 50+ chapters on topics such as one-on-one meetings, giving honest feedback, building trust, and more.
  • Toolbox — Dead simple software tools to help you run effective one-on-one meetings, ask for feedback, get high-level team updates, foster rapport, and more.
  • Community — Online support from 1,000 other managers from all over the world, where you can discuss tough situations like firing, hiring, and more.

You can read more about our resources here.

And, we’re not done! We’ve got loads of ideas for more guides, more tools, and more resources that we’ve already started working on creating. There’s so much to be done to help people become the leaders they’ve always wanted to work for.

Changing our business model.

For new customers who sign up for Know Your Team, we chose a new business model. Know Your Team costs $65/month per manager to purchase. As a monthly subscription, this makes it easier for managers to swipe their credit card without having to ask for permission from their boss.

Previously, our one-time pricing model had been useful to get us to profitability quickly. For example if you had 19 employees, we charged $1,900 one-time. We were essentially collecting the lifetime value of the product upfront.

But over time, we noticed our one-time pricing model becoming a big barrier to sales. A business owner had to justify a $2,000 or more expense to their finance department, to their investors, and to their leadership team.

Now that we’re selling to managers, there was no way a $2,000 product was going to feel accessible to them, even if the cost was only one-time. We wanted Know Your Team to feel like a “no-brainer” purchase for folks who might not have access to the company’s budget. So we moved to a monthly subscription model.

Building Know Your Team with two people.

We spent six months building Know Your Team. This meant designing and coding new features, writing 50+ chapters on leadership for our guides, and constructing a new billing system, new onboarding system, and new marketing site… All with just two people.

Every piece of copy, code, and illustration you see is something our CTO Daniel Lopes or myself created. (We did this while maintaining our current product, doing customer support, writing blog posts and pursuing other marketing projects.)

This is a big move for us. As a bootstrapped company, we don’t have piles of cash stacked up, in case it doesn’t work. We don’t have investors to run to if we get stuck in a bind. (In fact, we have $140,000 in the bank, to be precise.)

But, the change feels right. Since I’ve been running the company in 2014, this launch, today, is the most energized I’ve felt.

Why the weirdness?

Admittedly, our approach is weird.

You might be wondering, “Why are you making things so hard on yourself, Claire? Why not raise some money to make this change? Take out a bank loan or open a line of credit? Hire more people? Buy yourself more time?”

Those are not bad ideas. We considered them. And who knows, maybe we’ll pursue them in the future.

But for right now, the short answer is: I don’t want to.

When you run your own business, you have to remember why you wanted to run it in the first place. What you want. Not what others want.

In business (and in life), we’re addicted to pattern-matching. We snuggle into where the grooves are carved, where the tracks have been laid — not necessarily because we want to — but because they’re just there.

For me, I got into this whole starting-a-business thing because I wanted to do it on my own terms: Small in headcount, big in impact, independent, profitable. Life is short. Why build a business any different from your vision for it?

Of course, you shouldn’t mindlessly listen to your own din, in isolation. You should carefully choose who to listen to. The only people I want to listen to are our customers, current and prospective: Employees, managers, leaders, CEOs.

The minute you take on investors, accept money from a bank, put people on your board — you change the people who you’re listening to.

I don’t even want to listen to Jason and David, the founders of Basecamp (and Know Your Team board members) 🙂 We’re lucky that Jason and David want us to do things our way, too. We disagreed on some of the strategy of the roll-out of Know Your Team, but they were very supportive of us choosing to ignore their advice. (I’ll write more on this perhaps another time…)

If you have the luxury to choose who to listen to, choose intentionally.

Is Know Your Team for you?

You might be one of those people I want to listen to.

If you’ve spent late nights googling things like, “how to be a good manager” or “how to run a team meeting” or “how to delegate well”…

If you’ve bought carts of leadership books on Amazon, desperate to avoid beginner manager mistakes…

If you’ve ever thought to yourself, “I have no idea what I’m doing as a manager”….

Know Your Team is for you.

I’d be honored if you gave Know Your Team a shot.

If there is anything else — truly anything — I can do to help you become the leader you always wished you worked for, I’m here. Feel free to email me at or ping me on Twitter at @clairejlew.

I look forward to hearing what you think. I’ll be listening to you.

On the journey with you,

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

You have a micromanaging boss. What can you do?

There are 5 reasons your boss is micromanaging you. Here’s how to manage up, and around them.

I’ve heard the phrase, “I have a micromanaging boss,” more times than I can remember.

I heard it again, just last week. This person asked me, “What do I do? Is there anything I can say to a micromanager? How do I manage up?”

Here’s what I recommended to him…

First, identify the reason. (Yes, there is a reason.)

People do things for a reason. No one is a micromanager because they want to be a micromanager. No one hears that word and goes “Oh yeah, I want to be that.” In fact, for most leaders, to learn that we’ve become a micromanager is a sour, disheartening realization that sloshes around in the pit of our stomach.

So, if your boss is micromanaging you, ask yourself, “What might be causing them to act this way?”

Typically, your boss is micromanaging you for one (or several) of 5 reasons:

Reason #1: Worry

Your boss is worried about the outcome of the work and doesn’t think you’ll get it done.

Reason #2: Fear

Your boss’s butt is on the line, and they can’t have you make them look bad.

Reason #3: It’s All They Know

Your boss has only always had a micromanaging boss (or this is their first-time being a manager) — so they don’t know any other way to manage.

Reason #4: Past Experience

Your boss has been burned before by a prior employee who slacked off and didn’t produce results — and so this is their way of compensating.

Reason #5: You 🙂

You’re doing something (or not doing something) that is causing them to overstep and keep a close eye on things.

I want to be clear: These reasons do not excuse your boss’s behavior. Rather, they illuminate that micromanagement is not random, without reason, or out of malice (usually!). When you reflect on what’s driving your boss to be a micromanager, you can better calibrate how to work with them.

Also note that people are complex, and motivations are not neatly categorizable. The reason your boss is micromanaging might not perfectly fit into one (or any) of these reasons I listed above. However, having a hunch —a probable reason for why your boss is a micromanager — gives you wind in the sails to help change their direction.

Second, defuse the reason.

Once you’ve considered the reason behind why your boss might be micromanaging you, now you can take action. You can ask questions and take steps that loosens whatever is causing them to grip so tightly onto you and your work.

Based on what the reason is, here’s what you can do:

#1: If your boss is worried about the outcome of the work… Have a conversation about what success looks like.

Yes, this means defining what metrics or deliverables should be achieved. But equally critical are specific examples of what quality work looks like. “Quality work” is subjective, and as a result, what a leader is most concerned about. To get on the same page about success and quality of work, you can ask your boss: “What’s a previous project I did that measured up to the quality of work you’re looking for? When have I fallen short? What do you think is the best executed project you think the company or team has ever done? Why?”

#2: If your boss’s butt is on the line… Make it clear that you understand the stakes.

Your boss is likely more stressed than usual, and you don’t want that stress to be off-loaded onto you. Ask, “What can I do to relieve any pressure on your end? Is there any reporting you’d like me to do that would help make things more visible or consistent? Is there a crucial stakeholder I’m unaware about who I should consider? Is there a timeline I absolutely have to meet that we haven’t yet discussed?” Show that you’re in this critical situation together, and you’re willing to do your part.

#3: If your boss doesn’t know any other way to manage… Suggest alternatives.

This sounds intimidating, surely, but you can have this conversation in a non-threatening way. How? In your next one-on-one meeting, offer up “working styles” as a potential topic. Then when you sit down to chat, say, “I’d love to talk about our working styles and preferences, and how we each work best. How would you describe your working style and how you work best?” Then after thoroughly listening, ask, “Do you mind if I share mine?” You can also be straightforward and describe what changes in behavior you’d like to see. For example: “Ideally, here are things I’d like to see different. What can I do so you feel comfortable with those changes?”

#4: If your boss is acting based on a previous experience… Draw contrast to how you and this situation is different.

This is probably the trickiest of situations to really defuse well. Ask your boss, “What’s the best work experience you’ve had? The worst?” Then share yours. This will prompt a conversation about expectations and preferences — and what’s influenced those expectations and preferences. It also gives you a chance to learn how to adjust your own actions. You’ll learn that oh, your boss really didn’t like it when their former team member didn’t communicate decisions — and now you know to make decisions extra clear.

#5: If your behavior is causing them to micromanage you… Well, start doing things differently 🙂

This may be hard to admit, but sometimes our own behavior invites someone to micromanage us. We recently conducted a survey of 355 people and learned that the #1 piece of information that managers want to know is the progress that’s being made on a project. So it could be that you might not be sharing enough of the progress you’re making day-to-day or week-to-week. You can get to the bottom of this, by asking your boss: “How can I give you more visibility into my work or decision-making? What part of the job do you think I’m most shaky at?”

As they say, habits die hard. Very hard. You may not be able to kill their micromanaging tendencies completely, nor overnight.

However, you will be able to create some space. It might not be a lot, but it’ll be more than before. Over time, as you build more rapport and history with your boss, that space will grow.

You don’t have to silently absorb the incessant Slack pings or random taps on the shoulder asking, “Have you done this yet?” That’s not the only way to work.

You can have a healthy, productive relationship with your boss. You can help your boss not be a micromanager. Start here.

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 Desiree Vargas Wrigley, Founder + CEO of Pearachute

As a second-time founder who’s scaled a business to $5MM+ annual revenue and appeared on SharkTank (getting an offer from Mark Cuban along the way), Desiree shares her biggest leadership lessons on identity, team dynamics, and growth.

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 Desiree Vargas Wrigley, Founder + CEO of Pearachute. 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 honored to have someone who I admire, a good friend of mine. I have Desiree Vargas Wrigley, who is the founder and CEO of Pearachute, which is this amazing platform that helps anyone who has kids drop into any class that they want. I think it’s yet a brilliant idea and she’s really built and grown the company. Before that, was the founder and CEO of GiveForward.

Something really cool that Desiree was also telling me about was they’re actually now offering Pearachute as a great work park. So something you can actually give your parents who are parents to help them, yeah, just really engage and feel connected with their kids. So anyhow, Desiree, it is so amazing to have you here and to be able to ask you this one question about leadership.

Desiree: Thank you for having me, I’m excited to see you.

Claire: Thanks. Okay, so you don’t know the question in advance, so brace yourself. Here’s what I’d like to ask and here is what I’ve been asking CEOs and founders who I respect, which is: What’s one thing or it can be several things, you wish you would have learned earlier as a leader?

Desiree: That is a big question. Early on someone gave me this advice but I didn’t know actually how to internalize it until later. So I’m going to start with … I’m going to make it a two-part.

But the first one was that don’t beat yourself up too much when things go wrong, but also don’t take too much credit when things are going right. Because a lot of times there are things that are happening as a leader and as a company that are out of your control.

As much as you want to believe that you are driving everything, external forces really do have an impact and great hires of course make up … as terrible hires sometimes make an impact. At the end of the day, like yes, you are the one holding the bag as CEO, but it’s never all your fault or all your credit. It probably sounds obvious, but I think in the early days I really thought if I work harder or if I think smarter I’ll be able to solve this problem all the time. Sometimes there are really just outside factors and you have to learn how to navigate them and kind of remove ego from the scenario to be able to just really perform.

That’s one, and then … Two, figuring out what kind of leader I wanted to be. I think a first founder, a mistake that a lot of us have which is tied to my first part of the answer is that you are so closely identified with the business that you’re creating because it came out of your brain. It’s literally like your brain child and you are convincing people to come and work on it with you, and convincing people to invest in it. It is so closely tied to how you feel about yourself. So the ups and downs can be … You know, have a really big impact I think on your mental state but also on your quality of leadership.

The more you can remove your sense of self-worth from the performance of your business, the better your business and your leadership will be.

You’re able to see more clearly kind of where your baby is ugly or why certain things aren’t working. So just kind of having that level of knowledge and reflection, being able to separate yourself. One other thing that allows you to do well as leader is that when people underperform, it’s not that they are kind of violating this promise to your baby, but it is instead an opportunity to coach them and help them grow into a better version of themselves. All for the kind of same North Star as opposed to taking care of this child that you are giving them access to.

Claire: Absolutely.

Desiree: Yeah.

Claire: Wow. No, I can completely relate to that answer, having now sort of my third company and I think it is a hard lesson to learn Desiree. I think this idea that you separate your identity from the business. I mean, how do you do that, first of all, and second of all … Or maybe I should actually ask the second part first. When did you learn that? Like did something happen? Whether it was when you were starting and running GiveForward, whether it was when you were starting GiveForward, whether it was when you were starting and running Pearachute, where you realized, “Huh, I think I’m equating my sense of self too closely to the business and it’s actually having negative effects.”?

Desiree: Yeah. For me, it was a series of things that helped me fully, fully realize the separation. You know, bringing in a co-founder early on meant that I had to of course share the vision with someone else. But I think if I’m being honest with myself, it still always felt like mine and I was letting him in. Which is not a great way. We’re still good friends and we overcame I think the challenge in our partnership. But if I’m being really kind of just honest about how I treated things in the beginning, I think as you bring in senior team members, starts ruling some of your ownership over that control.

So in a way you kind of give up a little bit of that identification, tiny bits at a time. But truthfully for me, when I decided to step away as CEO and bring a new CEO. It’s not honestly something I would recommend to most people, it’s a very challenging way to do that, to separate yourself. A much healthier way is through coaching and through maybe therapy, reading, I don’t know, a combination of things.

I ended up working with an executive coach for a while who like helped me make a lot of progress and understand kind of my role within the vision, as opposed to being the creator of the vision.

So I don’t recommend getting a new CEO as a way to do it, I think there’re other ways. But sometimes it does take something daring like that to force yourself and then there is a grieving process, no matter how you do it. Because you are separating a piece of yourself and it’s not a divorce in any way, shape, or form, but it is retraining your brain to think about yourself and your value differently than you did before. It’s so liberating.

Honestly, this time around with Pearachute, I get to look at Pearachute as something that is on its own. I actually think truthfully being a mother has helped me do this that much more because I have two boys that I’ve birthed and then a step-daughter also.

My role as a parent is not to dictate who they become, right? But to help put them on this journey for success and to give them the foundation and the resources that they need to be their best selves. That’s true about a business too.

So you know, the analogy does continue, but one that is less emotionally aggressive I think, which is: If you treat your company as this being that has his own life, and its own identity, and its own brand – you create the resources and the support system around. It’s just such a much more relaxing place to live and you still want them to do well. You still need them to get into college, you still need all those things to happen but you’re not … It’s not the same as your own personal value.

Claire: Absolutely. What then are you doing differently with Pearachute in this approach? Is it a mindset, is it in conversations you’re having with your senior leadership team, has it affected your hiring? Like curious, given that you’ve learned, “Okay, I can’t be as emotionally aggressive.” what are you doing differently then with Pearachute to sort of set those boundaries?

Desiree: Yeah, I’m doing so many things differently. Definitely hiring.

I hire a lot more for the individual athlete role.

I think if I’m being honest with myself, before, I hired good people that I thought would be good at the job, but this time I’m looking for efficiency, and a lot of creativity, and a strong level of autonomy. Because this time around I just have so much more trust and I sometimes feel sorry for some of my earlier team members because I just didn’t know how to trust them with the vision.

This time around I have that clear understanding. So people can achieve so much more obviously when you are willing to kind of give them that freedom to explore and make mistakes.

Of course, they fail and recover from those failures, and wow you, right? So creating room for that within my team is really important to me. Because of that, I often think we get more done with our eight or nine people than we did with our 40 that we had before. Just because people are able to be really, really focused.

I am so much better at clearing a path towards creating time blocks for people and making sure that they have enough time to do their work. Where in the past I think we really jammed meetings because there needed to be a lot of communication.

I think if you’re transparent and constantly doing a great job of reinforcing vision and the kind of ways you’d attack toward that end goal. That you don’t need to do as much real-time collaboration because people have a clear idea of where we’re all headed. It’s more about checking in with each other and confirming priorities, and then kind of getting back to work.

Claire: Absolutely. Yeah, and I mean, I think there’re so many CEOs and founders who I talk with who struggle with this, right? Like you start a company, you’ve been kind of killing yourself over it and now someone else is going to start to do your job. So being able to sort of release that and just be a lot more hands-off. It takes a certain amount of discipline but it sounds like that’s really paid off and been the difference for you, between the two companies. Yeah, that’s amazing.

Desiree: For sure and I’m actually very practical with my team too. A lot of their roles right now are a jack of all trades, wearing many hats.

So I remind that our job is to build this company to be big enough that you kind of earn the right to either hire your boss or hire the person to take everything off of your plate that you don’t love or aren’t the best at.

That really, like that is the sign that we have gotten there, is being able to also then relinquish some of the things. Sometimes it’s things that you do love that you have to relinquish. But I think if you’ve got into the culture, it creates less kind of territorial-ism and more of a willingness to like let peoples’ skills flow into the places that we need them the most. As opposed to like this is my silo, that’s your silo.

Claire: Absolutely.

Desiree: Which is something also that we did not as well in the first startup.

Claire: Totally. I mean, what you’re describing Desiree is the struggle that has come up so often in these conversations, which is a struggle with ego and a struggle with … again, like almost a sort of possessiveness. Which is very related to the very first thing you said, which was kind of the first answer you gave around what you felt like your biggest lesson was. Which is that it can be very easy to feel like when things are going really well, it’s all you, and then when things bad, it’s all you.

So tell me a little bit more about that founder mentality or … You know, I don’t know if you want to call it a syndrome, I don’t know if you want to call it sort of a blind spot, right? But why do we get stuck thinking that when things are really good, it’s all us, and things are really bad, it’s all us, and what are the dangers of that? Like how has that affected your journey as an entrepreneur?

Desiree: Yeah. So a very specific example of this for GiveForward was … So we were a crowdfunding company, coming of age when Facebook was coming of age. We launched before Kickstarter but Kickstarter’s massive rise definitely helped elevate all of crowdfunding, right? So we falsely believed that because we were investing in SEO and paid search, and we had this great channel for distribution through Facebook, that the growth that we were seeing was entirely of our own doing. That we were figuring it out, we had the secret together.

Then it took the Facebook algorithm change to knock us down really big. We didn’t realized that we were growing on top of the growth of other giants, and that while we had been intentional in how we spent, we didn’t perfectly know how to find our customers. Our customers are very hard to find. The best friend of someone with cancer is a hard target, absolutely. But this time around, I have a better understanding of what kind of external factors can be contributing to growth.

At the same time, I’m more much laser focused on what are the measurable things that I can do within kind of our economics to create efficiency there. So that I can predictably know that when I put $50,000 into marketing, I’m going to get X numbers of customers out. So I think that comes with experience just in general and success. So now our user growth feels much more earned because I had that other thing to reflect on. But I’m also very aware that I am now sitting in a company that is targeting mostly millennial parents and only 20% of them have started having children. So there’s this massive group, that’s 80%, that is about to have children.

I will assume that our growth and rise to power will be because of what’s happening within these external forces. You know, paying attention to both I think helps to remember that like it’s not … Everything that you’re doing is not perfect and something that works now obviously might not work again in a year. But it’s when you’re in the middle of crazy growth, it’s hard not to pat yourself on the back and say, “Look how amazing we are. We’ve done all these things right.” The truth is, a lot of it is about timing.

Claire: Yes. I think that advice is worth its weight in gold. Because I don’t think you learn it until you get burned by that situation and you realize, “Huh, I think we made a lot of assumptions.” I guess, what advice do you have for founders and CEOs to be rigorous about not assuming that it’s all you? It sounds like from your perspective, the analytics, the level at detail that you’re looking at, like you were saying the metrics are really key. But is there something also you’ve embedded in your team, are there sort of systems you place in Pearachute? Curious just about advice you would give to other founders to do that well?

Desiree: Yeah. It’s so tempting, right? To find this path that works and double down. So yeah, that is an element, of course, with any level of growth. But for me, I am very aggressive with my team about diversifying acquisition. That paid search is great, or any kind of paid ads are great, until the cost of acquisition gets so high that you have a ceiling and you can no longer spend to affordably acquire your customers depending on your LTV.

So we have been conscious of the pieces of acquisition and since the very beginning knowing that, of course, there’s a viral component to the business, there’s also a direct, which is a little bit harder to manage or influence. We need to be working kind of equally on all parts, because at the end of the day, full reliance on one channel has very high risk of creating really expensive customer acquisition down the road.

Claire: Absolutely.

Desiree: So I would say just constantly diversifying, yeah.

Claire: Again, I think everyone who is watching this will be taking notes and writing that down. Desiree, thank you so much for sharing.

I’ve been learning a lot just listening to you. Like I said, you’re someone who I’ve always really, really enjoyed hearing about your experience in building and growing companies. So thank you so much. I know everyone who is watching has really appreciated your thoughts too. Thanks.

Desiree: Thank you for having me.

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.)

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

Managing disagreements: How to handle diverging points-of-view with your boss

Six leadership tips on what to do when you disagree with your boss (or another senior leader at the company)

It’s inevitable: You’re going to disagree with your boss. No two people on the planet agree with each other on everything, 100% of the time.

That’s a terrible idea,” you think to yourself, after listening to your boss share a decision she’s come to. “She strongly needs to consider an alternate option.

Yet, managing disagreements at work is tricky — made only trickier if the person you disagree with is your boss. Of all people, you don’t want that person to get defensive or misinterpret your disagreement as an attack. You want whatever thing you’re arguing for to be considered, and hopefully enacted.

The key is to share your opposing point-of-view respectfully — and effectively — so the outcome you’re looking has a higher likelihood of happening.

So, how do you do that? How do you disagree productively with your boss, or another senior leader on the team?

In The Watercooler, our online community for leaders, managers from all over the world suggested taking these five steps when you and your boss disagree:

Peel back the layers of “why”

Start with the assumption that people are reasonable and make rational decisions. Then, ask yourself, “Given that assumption, what would have to be true for them in order to cause them to make the decisions they did?” Are there other priorities they’re managing that you’re not aware of? Are there other stakeholders who have an interest in the outcome that you aren’t considering? Rigorously peel back the layers of their rationale to figure out what those underlying reasons are.

Emphasize the common destination, not the divergent paths.

You’re both on the same team. Remind them of this. While trying to explain your own view, extrapolate the assumptions, beliefs, and values you both have in common. For example, you both care about the team’s success, you both value speed over perfection, you both see X priority to be most critical. What you most-likely differ on is the approach: The strategy to execute, the timeline, the resources, etc. Highlighting the points of agreement re-centers the conversation: While the roads you mapped out are different, you both want to end up in the same place.

Show, don’t just tell.

Evidence is compelling. How can you show — and not just tell — that your recommendation or idea should be taken up? Is there anything that you can work on that directly contributes to the company primary goals and illustrates your point? For instance, one Watercooler member discussed how she started a project without many resources, and eventually recruited people who shared similar views to build her case. It worked — her boss implemented the idea.

Consider: What is the one thing you can fix right now?

When we see a lot of fires, our urge is often to build a brand new fire station. However, in reality, all we might need is to find the nearest fire hydrant to hook up to. If many things are broken and you think you know a better way, avoid the desire to solve everything at once. Focus on just one thing that can be a visible quick win. Connect to the fire hydrant, first. Then, you can better make the argument to build the fire station for the neighborhood.

Ask yourself, “Do we really disagree on core beliefs?”

Sometimes, the gap between the opinions of you and your boss isn’t just a crack — it’s a chasm. It’s much wider and deeper than you initially thought. This is important to pay attention to. If you disagree with a coworker on core beliefs, then the change will be an uphill battle. You’ll want to seriously consider if it’s worth the trouble. And, if it’s not, perhaps it’s not the right company for you to be at. Core principles that you want to be aligned on include: your beliefs around company culture, how managers see and respect employees, the ratio of autonomy vs. control, iteration process, team structure and long-term goals.

Look for an outside advisor or mentor.

A third party can bring objectivity to a disagreement. One Watercooler member recommended how this option is helpful when the conversation becomes circular and isn’t progressing in a positive direction. Having someone fresh can not only be useful to moderate the discussion, but provide new insights that you both may not have considered. However, when doing this, it’s important to set clear expectations, and decide on how to handle the outcome of the discussion. You don’t want the outcome to devolve into office gossip because you “brought someone from the outside in to help.”

These tips have helped orient my thinking around approaching differences of opinion within my own team. I hope they help you too.

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

Feeling “off”? How to be a good manager when you just don’t feel like being one

If you’re struggling to stay engaged as a leader lately, here are some leadership tips to pull you out of the slump.

Some days, being a good manager is more difficult than others.

You can’t focus. The day drags. You feel “off.”

The company isn’t doing as well as it used to. Or you received a scathing email from a client. Or you’re questioning the latest shift in the company’s direction.

Whatever the reason may be, there’s no shame in it. I’ve had these “off” days, myself — and so many other leaders have too. As companies go through highs and lows, and our mind and emotions ride the highs and lows along with it. In our online Watercooler community with almost 1,000 managers, many folks shared this sentiment: We all “occasionally fall into slumps where being a good manager becomes more difficult.”

The question is: How do you handle “off” days, so you don’t stay discouraged as leader?

Here’s the advice that our Watercooler members gave to overcome the work doldrums:

Take a day or two off.

Perhaps this sounds like conventional advice when you’re feeling “off” — but it’s because it works. Go somewhere quiet and get away from anything that could remind you of work. No phone, no emails, no talk about work. Studies have shown how beneficial “unplugging” from technology is in particular to clear your head. Use this time to re-evaluate your priorities, the things that motivate you, and the sort of contributions you can make to your company and team.

Focus on the impact you have on the people you work with directly .

Even when you’re not particularly motivated by your company, think of the impact you can have on people’s lives and their careers. As a manager, your attitude and actions shape the everyday lives of your direct reports.

Revisit your team’s vision and purpose.

This should be the “why” behind your work, and re-evaluating it and can invigorate you. One member of The Watercooler did this by meeting with each member of his team to get their perspectives on the company’s direction. He listened to their feedback, looked at the market and their competitors, and reshaped the company’s vision accordingly. The adjustment in the team’s purpose gave him greater purpose to show up for work each day.

Dig into the work itself.

Sometimes you feel in “funk” at work is because you haven’t been able to be in a state of “flow.” Choose to get back to more hands-on work to make progress on something you love to work on. Before you were a manager, were you a programmer by trade? Roll-up your sleeves and write some code. Do you work at a public relations company and used to be the one interfacing with journalists all the time? Put together some traditional media pitches and pick up the phone. Reconnect with what you love to do most.

Switch up your role in the company.

You might be feeling “off” because you’re not in the right position in the company. One Watercooler member mentioned how he changed his role in to a “visionary” one (think CEO) rather than an “integrator” one (think COO). He then realized he was better suited — and qualified — for big-picture thinking than operating the business.

Consider going on a “work retreat.”

You could be missing some of the unstructured creative time you had prior to being a leadership position. To combat this, one Watercooler member will take little work retreats a few times a year where he can recharge his batteries. He normally spends about a week in an AirBnB in some random city all by himself. It’s like a vacation in the sense that he completely unplugs from his normal responsibilities, but instead he just works on design/programming.

Now, of course, these are not solutions to remedy serious core company issues. You may be feeling “off” for important reasons that you need to resolve: Your team culture is toxic or your work habits are unsustainable. Pay attention to the underlying reasons causing the “off” feeling.

Rather, these suggestions work well as a short-term boost, when you know it’s merely an “off” feeling, and you’d like to steady yourself.

If you’re stuck in a slump as a manager, you don’t have to stay in it.


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.)

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.)