As the CEO and Co-Founder of a $35MM+ revenue company with over 2 million users, Wade shares what he wishes he would’ve learned earlier about intellectual honesty in management, feedback, and running a remote company.
Every few weeks as part of The Heartbeat, I ask one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interview Wade Foster, CEO and Co-Founder of Zapier.
Claire: Hey everyone. I’m Claire Lew and I’m the CEO of Know Your Team. And I am thrilled today to have on The Heartbeat, Wade Foster, who is the founder and CEO of Zapier, this amazing integrations platform which we use every single day at Know Your Team and who knows how many ways that we use it and depend on it. And we’re not the only ones, so Wade has built this amazing company with over 200 people entirely remote. I believe, over 35 million in annual revenue. Only raised one small round of funding. I know you came out of YC back in the day.
All the numbers are really impressive, et cetera, et cetera, but what I’m actually most impressed by, Wade, is just his humility and how he’s chosen to build this company really with an eye for the long term.
So, excited to chat with you today, Wade, and to ask you this one question I’ve been asking leaders I admire. It’s a surprise.
Wade: Oh, boy.
Claire: With some of my guests, we had talked about this earlier, they get the question in advance, and sometimes they prefer it to be a surprise. And Wade was like, “Alright, I want this to be a surprise.” So we’ll see how this goes. You ready?
Wade: Let’s do it.
Claire: Alright. So, this one question about leadership I want to ask Wade is, what’s one thing you wish you would have learned earlier as a leader.
Wade: Can “everything” be an answer?
Claire: If you’d like, yeah. We have all day.
Wade: Shoot. One thing I wish I knew earlier … There’s a lot of things I wish I knew earlier.
I think the thing that’s probably most, if there’s one thing…I think there’s this pressure when it’s your first time that you just know everything. That you instinctually have all the answers. Like you’re put in this spot for some reason, destiny or whatever. This is the reason, and you’re the person who has to be the oracle. You know everything.
I think I’ve found throughout the years that people really just enjoy working with leaders who have a little more intellectual honesty around this sort of stuff. They are just real when they don’t know the answers. But also confident when they do. And can help people just navigate the hard times a little bit.
When you do this well, the organization just gets better at solving problems, because they’re able to be more honest with each other. If you as a leader are willing to say, “I don’t know the answer. There’s going to be times in the future where I continue to not know the answer. I’m not the best in the world at this job. That’s just how it is.” And you kind of just get that out there. It frees everyone else to say, “Okay, it’s okay for me to also not be the best in the world at this thing.” And we can kind of get rid of this façade of like we’re all going to be great, and just get to the reality of the situation, which is that we’re all flawed people, our skill sets are all imperfect in some day.
We all wish we were better at things that we are trying to do. And just be honest about that and so then when we reach problems in our work, we can just try and solve them together, and just be like, okay, you don’t get this. Here’s how we’re going to figure this out. It just cuts out a lot of this theater around working and gets straight to the heart of, this is the problem. How are we going to fix this? Nobody’s fault that we have this problem. We’re just going to deal with it.
And so I think early on, I spent more time trying to pretend to be better than I probably really was.
Claire: Sure, play a character, right?
Wade: Yeah.
Claire: And like you were saying, this theater of leadership. I couldn’t agree more with that in terms of, it’s a huge reason I do the work that I do is because I look around at all this stuff that is projected about leadership, and I’m like, these are relics and fairytales of what we would like to think to be true. And to your point, there’s this fascinating dichotomy that comes with admitting mistakes, being more grounded, taking away that façade, and then that actually leading to being able to solve real problems faster. And actually, the quicker you are the reveal your weaknesses, the stronger you become. Which is this very odd dichotomy. It just doesn’t really compute, I think, like you were saying initially.
And we’ve built so much expectation for the inverse to be true. So, I’m curious for you, Wade. You built this company first in your early 20s. When did this realization hit you? Was it pretty early on? Has it been more recent? Was there sort of like one aha moment where you were like, oh wow, this is something we need to find a way to maybe really embed more into Zapier, maybe in the way that we hire. Just curious how this revelation really came about for you.
Wade: I don’t think there was an aha moment. I think it was just kind of like a series of experiences with individuals, with hearing from other leaders, like how they approach things. And third, just trying some of this stuff myself, and then seeing how people respond to it. And you start to go, wow, that went better than I thought.
Claire: Yeah, always a good feeling.
Wade: Yeah. It’s like wow.
People are cool when you don’t know the answer. People are like, oh, that’s fine. I don’t know the answers to a lot of things myself. You try it and you just realize, oh, nothing broke, no one quit, bad things didn’t really happen.
You have this fear of it, and when you start to do it the first few times, you’re like, oh, wow. Nothing bad happened. And then you also start to see the upside of it. People start coming to you and they’re honest about the situations. They’re not trying to … If there’s a project status update, and they come in and don’t say, “Oh, it’s going great. Everything’s fine. Nothing’s wrong here. Don’t look over here. It’s all good.” That’s stopped happening, and they start coming to you and saying, “Hey, there’s … yellow flag. This is maybe going to cause a problem over here.” And so all of a sudden, you start to see … You get to reap the rewards of planting this intellectual honesty within the company that is, I think, really helpful.
People start coming to you and they’re honest about the situations. They’re not trying to … If there’s a project status update, and they come in and don’t say, “Oh, it’s going great. Everything’s fine. Nothing’s wrong here. Don’t look over here. It’s all good.” That’s stopped happening, and they start coming to you and saying, “Hey, there’s … yellow flag. This is maybe going to cause a problem over here.” And so all of a sudden, you start to see … You get to reap the rewards of planting this intellectual honesty within the company that is, I think, really helpful.
Claire: Absolutely. And I love that framing of intellectual honesty, because I think the framing of it really matters to how willing we are to participate in it. If we say it’s talking about how you’re not smart enough, or talking about how you mess up all the time, or talking about how you’re not good enough, we as leaders, we’re not as likely to want to participate in those things. But to your point is this idea of intellectual honesty. Of a rigor and an openness to what’s actually true instead of what you want to be true. I think that definitely encourages folks.
One thing I also wanted to ask you about, Wade, is we had had a previous conversation prior to this podcast where I had asked you, so this whole leadership thing is so hard. And learning lessons like these are so difficult. And I’d asked you why do you think it’s so hard. Why was it so hard for you to learn that lesson. Love to talk a little bit about that.
Wade: I think a thing for me that made it tough was you start as a founder, and for founders in particular, I think we tend to be wired in a certain way where we feel like we can just figure things out. We feel like we don’t need a manager to coach us. Like we don’t need this extra hand holding. Or sometimes you don’t even want it. I certainly know that was in my case where it’s like I’d had bosses before and I’m just like you’re not helping me. You’re actually making my job harder. And so, as a founder, you start to think … You translate I’ve had a bad boss, to all bosses are bad, which is not really the case. But I’d made that translation. And so you start to say, our organization doesn’t need management, or we don’t need these types of things.
I didn’t need it. I figured it out on my own. Why does anyone else in our company need this? So you start to tell yourself that story. And I think it takes a little while to just unwrap that belief. You’re like, I figured it out myself. I just don’t get it. And it took me a bit to really lock in on, oh, I had bad managers. Not all managers are bad. It took me a while to make that transition.
And the thing that really helped me out is, in addition to reading stuff like the Know Your Company blog, there’s a really great podcast called Manager Tools that … It’s two old, or like West Point grads who worked at PNG for a long time, who just have this very no nonsense, sort of practical approach to management, where most of the material out there stays so high level and it stays so fluffy that it’s just like I can’t do anything with this. This doesn’t tell me what to do when someone walks into my office and they … Well, walks in to my virtual office in our case. But someone gets on a call and they say, “I want a raise right now.” Or they come in and say, “So and so didn’t treat me right.” Or these kind of tough situations that do happen in management. Hopefully you don’t experience a lot of them, but the longer you manage, you’re going to have these situations pop up and you’re not going to be prepared for these.
So the thing that was so great about them was I started having more of these experience and realizing I’m out of my depth to have these conversations. I just don’t know what to do. And my instincts are actually causing more problems.
My instinct to do it this way or to solve this problem this way is actually creating other problems across the organization.
And I started listening to this podcast, and they just have these tips and tricks that are like, in your one on ones, ask this question. When someone says this thing, this is how you give feedback. When you have these situations, literally down to, these are the words you should use and how to say them. I was just like, “Oh my god, this is so helpful.” And I totally see the value and what good management is. It’s not this weird thing that I … picture I’d painted in my mind. It’s this very tactical skill that people can learn.
That was, in my mind, that’s kind of my journey, and why it was tough for me to just accept, oh, management is a thing that’s important, and I should learn as someone who’s running a company out the gate, it took me making a few mistakes to get around and figure out, oh, this is a skill I have to work at just like any other skill you might have to develop in running a company.
Claire: Absolutely. Well I think it’s fascinating how much our past experience with a leader or good and bad colors how we choose to lead, or if we feel like we don’t want to lead at all. Or disregard management. And I can completely relate to this idea of … I had a terrible, terrible manager after I started my first company coming out of college. And it’s easy to think is this a thing that people should even be doing? So I loved the ability to reflect and to see that.
And the second thing that mentioned, Wade, that I thought was fascinating is you said that a lot of your instincts around how to do things in the company actually were not helpful. And it took you to sort of listen to this no nonsense approach and to hear really tactical advice about how to address it. Tell me a little bit more about that. Is there a specific situation? ‘Cause I feel like this happens all the time. And I notice this in myself and with all the research that I’m doing is a lot of our initial instincts for how we think we are helping our team actually hurt. How do you feel? Talk to me about how you’ve experienced that
Wade: Sure. I’ll give you a very tactical thing. And I think, certainly myself and a lot of first time managers make the mistake of, and it comes back to the very first thing I said, which is knowing the answers. Someone comes to you and says, “I have a problem.” And you’re like, I’m the manager, I’m the boss. My job is to solve the problem. So you jump in and solve the problem. But when you do that, you’re actually mistaking your roles. You’ve hired this person to solve problems. And if they’re unable to solve the problem, you’ve probably hired the wrong person.
Now, that doesn’t mean that people that come to you should have to solve problems all the time, but when they come to you with problems, it’s not your job to step in and fix the things that they can’t do. You’re missing out an opportunity to help them level up and be better.
But your instinct, when you’re a manager, is the first time someone comes to you problem is be like, this is it, this is my spot, this is why I’m here. I’m going to jump in and solve the problem. But that’s the exact opposite thing that you should do. Now all of a sudden everyone in your organization, you’ve become a crutch for them. You’re the person there that solves all the problems. The bigger your company gets, you’re this massive bottleneck because no decisions can be made, no problems can be solved, without it routing through you. Which, I’m sure there’s some people out there that would like that as the way they run their company, but that’s certainly not me. I do not want all decisions to run through me, and problems to be solved through me.
And so, it took me a while to realize, okay, when folks come to me with a problem, I need to respond to that in a more Socratic method way. I need to ask questions back to them. Like okay, well, what have you tried? Well, what are your instincts for the next steps? What do you think is the next place you should go? Ask more of these sort of probing questions to see if they can come to that understanding on their own. ‘Cause a lot of times, when people have problems, they actually know the answer. But they don’t like the answer. Or they’re uncomfortable with the answer in some way. And so you’re trying to just help them get to that realization that, you know what to do. Just go do it. And it’s not going to be as scary as you think it is.
Claire: Absolutely. I think it’s, in so many ways, so in line with what the definition of a manager is to begin with, which is it’s not to actually make the decisions, but it’s to create an environment for people to do their best work, and to make the decisions themselves. And that’s where the leverage comes from in leadership, is that you’re not the one doing and executing all the things. You’re helping other people do that. And it’s so easy to lose sight of.
Wade: Totally.
Claire: Yeah. Well, so Wade, I’ve like a million questions for you, but I’ll pick just a last few here. As a remote leader in particular of a 200 plus rapidly growing company, and I’m sure you get questions like this all the time, but I know of our audience in particular, they would love to hear how does one’s leadership style have to adjust, if at all, in your opinion, to running a remote company versus in person? And it’s interesting. I actually wrote a piece on this maybe a year or two ago, and I actually quoted some of the things that you had talked about. And it got a ton of traction and was widely spread, because people are fascinated about this topic. It’s like if I join a remote company, and I’m a new manager or I got hired as a CEO of a company that’s now starting to become remote, are there things you feel like you have to do differently? Or double down on and focus more, in your experience?
Wade: I think the more I do this, I think the core psychology of management is the same, no matter if you’re in an office or if you’re remote. The principles still apply. You’re still trying to empower people to solve problems. You’re still there to provide feedback. You’re still there trying to help the organization hit its goals. All those things are the same. There’s just no differences.
The places where there’s differences are just smaller tactical things. Like how you run your meetings. I feel a little different, because you’re not sitting in a conference room, and instead you’re jumping on Zoom or something like that. Maybe you’re giving feedback over Slack more so than in person. And so you have to create a culture that’s maybe a little more open to written feedback versus verbal feedback. Whereas a lot of the management stuff says, oh, you should deliver feedback face to face. It’s better to do that. But in a remote company, that actually can be a little more awkward at times, if you’re like, “Hey, can you jump on Zoom real quick?” It’s like, oh shoot, what’s going on here? Versus saying, in Slack, the informal thing to do in a remote company is to send a quick DM and just say, “Hey, heads up, I noticed this thing, maybe try doing it this way next time.” And sending that in Slack is actually the more informal, comforting place to do that.
And so there’s just some of these smaller tactical things that are different in a remote company. And you have to just live some of this stuff to figure out what those tweaks are.
But as long as you remember the core principles of what makes a good manager, you’re going to be able to do well in a remote company, or an in-office company, because the skill set is still more or less the same.
Claire: Yeah. I completely agree. I think, like you were saying, at its core, leadership is about communication and creating the right environment for people and being supportive. All that good stuff. I think it’s fascinating in talking to so many remote CEOs and managers just how the emphasis, to you point, is shifted. So this idea of paying attention to non-verbal cues as a manager is a lot harder to do. Paying attention to the morale level is a lot harder to get the sense of when someone is bothered by a certain situation. Are there things that you feel like at Zapier you’ve tried to, whether it’s in the culture that you create, or even small tactical things, to compensate for the fact that you might not always be picking up on non-verbal cues? Or like you were saying, a lot of the feedback and communication is going to be written versus face to face.
Wade: Yeah. I think this is probably the hardest difference between being in an office and being remote. And when you’re in an office, you as a manager can see when someone’s shoulders are down and when they’re disengaged in a conversation. You can see when they’re kind of checked out. It’s harder to pick up on that in a remote environment. So you have to be just extra observant. You have to read the tea leaves a little bit more. And be willing to just ask the conversation.
And I think be open to being wrong about it. There’s times where I’d said to someone, “Hey, I noticed you put this message in Slack. I just wanted to ask, hey, is everything going alright?” And they’re like, “Oh, no, it’s fine. No big deal.” And you’re, “Okay, sorry. I just misread that. Not a big deal.”
You have to be willing to ask the question, because otherwise you might actually literally have situations that are kind of boiling under the surface across your organization.
And because you’re not in person and it’s hard for people to realize that there’s some sort of tension or this team isn’t collaborating in a good way, that can linger for longer. And the longer that stuff lingers, the more toxic the organization becomes. And so you have to be willing to just, as soon as you notice a thing that feels weird or feels off in some way, you just have to ask the question and just be like, “Hey, I noticed this, and I just wanted to see, is everything okay?” Or, “I wanted to just check in and see if there’s anything I can help with.” Be willing to ask those conversations. And be okay with being wrong on some of that stuff. If someone says, “No, it’s all fine, my cat accidentally hit this key,” or whatever …
Claire: Sure. Here’s the thing. I know that we’re laughing about it, but what an important point, though, about this willingness to be wrong. And this is sort of a theme that we’ve had in this conversation, but a willingness to say, “Oh, I misread that.” Or, “Oh, okay. Nevermind. Not a big deal.” And, yeah.
Wade: I know I occasionally will freak the team out because my communication style is short and direct. I don’t flower up my messages in Slack often. And when I’m on mobile, especially that’s the case. So if you ask me, “Hey, do you think we should do this?” I might just say, “No.” And people are like, wait, what? It’s like well, I’m out and about with my wife or I’m in a meeting, and it felt like this was an urgent thing and so I wanted to get you my opinion sooner. That’s where I’m coming from. I’m not saying, “You asked a dumb question,” or, “This is crazy,” by just having a one-word “No” answer. You’re reading more into it than is there. And so I actually have to, when I onboard people into the team, I have a whole guide for, here’s my communication style is. Here’s how to understand when I say certain things. How to react to that sort of stuff. Just to get people comfortable with it. And then, of course, I try and adapt too.
Claire: Of course.
Wade: There’s times where I catch myself doing “No” with nothing else and I start to think, I can probably give a better answer than this one-word answer here.
Claire: Definitely. Definitely. Well I think a remote environment, being heavily text based, we talked about some of the negative consequences. I also find that the physical separation, especially for high pressure situations, or high emotion running situations, can be extremely helpful. So if I’m having an argument with a team member, or I strongly disagree about something, or I’m offended by something that someone said, it’s actually extremely helpful that we are not in person, in the same room, having the conversation. That it’s over Basecamp and I can have a moment to think about, okay, how do I really want to respond. Or let me reflect on the conversation. So I think the space is, as with anything, positives and negatives.
Wade: Yeah. There’s pros and cons. I was talking to another fellow CEO, and it was in a group setting, and so someone had posed a question like, what’s the toughest part of your job? And for them, they had a glass conference room. And for them, just being under the lens was a very difficult thing for them. And so they were like I have to really watch how I react to certain situations, because the team can see me. The way it was set up in the office, it was a very visible spot in the office, and it was a glass conference room. So they can literally see right through what’s going on and stuff like that. So there was a board meeting, or I don’t know. Something crazy. And I kind of was like, oh my god, I have never experienced that phenomena. If you and I were to get off this call, and I was like, sheesh, Claire just doesn’t get it, I can react with whatever facial expression.
Claire: You can do that, yeah.
Wade: He was like that I feel like. And the thing is sometimes you need that healthy way to blow off steam. My gut reaction might be, Claire just doesn’t get it, and then I’ll go walk the dog and I’ll be like, you know what, actually, there’s a thing that I don’t get here. And I need to clarify that with Claire. We need to talk through that piece of it. So you can kind of have your moment to just be human for a second in a remote company a little easier. So that’s certainly, in my case, I think that’s a pro.
Claire: I completely agree. And I think it’s been my saving grace on many occasions to just have a knee jerk reaction, that we’re all susceptible too. Well, Wade, one last thing I want to ask before we head out here. I want to actually circle back to the very beginning of our conversation, because your reaction to this question of what’s one thing you wished you would have learned earlier, you said, “Can I say everything?” And so I know we touched on a lot of different aspects, but I guess for our audience here, is there anything else in particular that you’re like, don’t make the mistake that i did. And I really wish I would have known about this as a manager?
Wade: Sure. So I think the other thing that took me a while to get comfortable with is just how to give feedback and really what makes good feedback. I think I’m naturally a people pleaser, like I want people to be happy. And for other folks who are people pleasers, they probably have experienced this moment where they’re like, oh my goodness, I have to give feedback that is not going to make this person happy. And that’s a tough thing to cross. And so, there’s a lot of books and a lot of people have talked about this. You know, Crucial Conversations and Radical Candor. All this sort of stuff. There’s 300 page books for what’s relatively simple concept, I think. And for me, that was another thing I really just had to get better at out the gate.
I think the realization for me that made it stick was, if you care about this person, truly care, not sort of fake, superficial, well they’re my employee, so I’m supposed to care.
But you really genuinely do care about this person, and if you understand what their ambitions are, what their dreams are, what their goals are – if you notice something that you think would help them achieve those things, and you hold that back, that’s actually not a very nice thing to do.
Claire: Absolutely.
Wade: Getting that to click for me took a while. But once it did, it just made it easier for me when I’m talking to this person. It’s like, they know that I care about them. They know that I’m in their camp. So when I share something that’s maybe a little tougher, they’re not going to freak out. And it just made it easier for me. The reality too was most of it was me getting tied up.
Claire: Interesting.
Wade: The person on the other side, not always, but the person on the other side, after hearing it, and especially if you give feedback in the right way, after hearing it, they’re thankful and grateful, more times than not. There is a separate set of management where sometimes you have to deal with a person who’s never got feedback in their life, and it’s just like that’s a whole other thing to deal with. But most folks are very accepting and appreciative of direct, caring feedback.
Claire: We could spend hours just talking about this one subject. It’s a thing that, we run four-hour workshops on it, to your point. Because it’s actually a really tricky thing to become good at and, hey, I even do this for a living, and there are situations where I’m like, huh, I’m going to have to really think about how I frame this. ‘Cause I think also one thing that we don’t often talk about is who the feedback is coming from. I mean, Wade, you are the CEO. And I think when you become a new manager, you become a new leader, you forget how much your word does weigh on a person. And you can overcompensate for that too. You can think, oh, gosh, because, oh, this person’s going to take my words so serious, and so I have to be so careful and so … And to your point, what really is the overlying factor of what trumps everything else is just the intention behind it.
The reason why people even get defensive to feedback is because they misread the intention. They think you’re out to get them. They think you’re making a personal attack. They think that you think less of them as a human being. And the minute that you can actually establish what that intention is, everything else sort of falls into place.
Wade: Totally. The words do matter in the feedback you give. You have to think deeply about what the message is you want to share. My co-founder, Bryan, was just writing on this topic for the team around a specific set of feedback. One of the thing we’re trying to do is we’re just trying to be faster in our go-to-market, and faster in how we respond to our customers. I think a lot of orgs are trying to just generally be faster. And so often times, as an exec or a leader, your feedback might default to, hey, I wish you were faster. It’s a very common piece of feedback. And the nuance that Bryan observed, which I think is an important one, is that, when the feedback is delivered as, I need you to be faster, often times what’s heard is, you’re going slow, or I think you are slow at your job.
What he would posit was, well, actually, that’s not the message I’m trying to deliver. Typically, what I’m saying is, you need to focus on a particular set of work better. So it’s like, you’re actually spending time on a set of work that doesn’t matter, and maybe you need to spend more time on this thing that does matter. And so, time by the wall clock actually ends up going faster because you’ve cut out this set of work.
Anyway, that’s a long-winded way of giving an example of the feedback that you deliver matters, because people are going to hear it in a specific way.
I do think it’s important to think thoughtfully as a leader and as an executive, “What is the message you want to be heard?”
So you should think about, okay, what is the behavior I want this person to do? Do I want them to rush through work? If I say I want you to be faster, they might actually hear that and say, “Oh, I just need to rush through this work faster.” Maybe that’s what you want, and so maybe you do deliver that feedback. Or is the behavior you want them to focus more intently on this side of work. And this is where you say, “Hey, I want you to get better at prioritizing your time.” And that’s a different conversation than speed. But the results that you get out of as a leader is actually speed.
So I think thinking through some of that as you give feedback is really important. And anyway, yeah. Like you said, we could have a hours long conversation on how to give feedback. It’s a hard one.
Claire: Absolutely. But I think this amazing take-away that I really hope that folks who are tuning in hone in on, is this idea of zooming in on the desired outcome instead of just describing the symptoms of what you think is wrong, and giving feedback about the symptoms. Oh, I think you’re fast, or I think we’re … I even think sometimes saying feedback like, oh, we’re focusing on the wrong things. Then it’s like, oh, I have to re-prioritize everything. It’s like no. It’s like just spend more … It’s like even more specific about the desired outcome, right. It’s just actually just spend more time on these things. And maybe the desired outcome, right, like you were saying, is you are quicker and don’t care about making as many mistakes, and you can cut corners here, that’s totally fine. Or, to your point, it’s just very much about cutting things out, which is a very different discussion.
Wade: Yeah. It could be as simple as pop open the calendar and say, “This meeting, you’re going to this 90 minute meeting every week. Are you getting value out of it?” “Oh, I’m not.” “Okay, great. Now you have 90 minutes freed up to do something else.” It could be as small as something like that that actually gives you a lot of time back to go try and do a thing. 90 minutes is plenty of time to do many tasks. And so all of a sudden, you might give the perception of being faster, because you’ve freed up 90 minutes in your day to focus on a task.
Claire: Yes. And that action is very different depending on the message that you are delivering. You might not get that same outcome if you were to just say, “Go faster.”
Wade: “Be faster.” Yeah.
Claire: No, this is an amazing reflection actually for myself and my own work. And I know for all the other managers and leaders who are tuning in, they appreciate it as well. So, Wade, thank you so much for joining us. It’s been awesome.
Wade: Yeah. It was a pleasure, Claire. Thanks for having me.
Claire: Cool.
