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Episode 49: Interview with Matt Westgate, CEO and Co-Founder of Lullabot

The Heartbeat Podcast - Leaders share their biggest, hardest lessons learned. | Product Hunt Embed

As CEO and Co-Founder of Lullabot , Matt Westgate talks about starting a company from scratch, teaching himself what he needed to know about business, leading with authenticity, and encouraging his company to talk openly about mental health.

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 Matt Westgate, CEO and Co-Founder of Lullabot.

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CLAIRE: Hi everyone. I’m Claire Lew and I’m the CEO of Know Your Team: software that helps leaders avoid becoming a bad boss. I am completely thrilled to have someone on The Heartbeat today who I’ve known for awhile, I’ve really admired for a while. And it’s a real honor to welcome Matt Westgate on the show.

Matt is the CEO and Co-Founder of Lullabot. They are a completely remote company that has been doing amazing Drupal design, development, and strategy for the past, I want to say more than 10 years. And they’re an extremely established firm that has clients, everyone from Martha Stewart to Georgia.gov to MSNBC to IBM. And I’ve respected Matt a lot because admits the really difficult, I think, industry of building a sustainable digital agency, he’s managed to do it with an entirely remote company and the ethos, Matt, that you really have around thinking intentionally about how you treat your employees, creating the best work environment. I always learn a lot when I talk to you. And so, I’m really excited to have you on here today. There’s a ton of questions I’ve got around everything from remote work to building a company that you likely didn’t know was going to turn into what it is today. But before we even get into all of that, I do want to start with this one question that I ask every single person who I have on the podcast. And Matt does not know this question, everyone. So, coming to you completely live. The question is, what is one thing, or it could be several things, that you wish you would have learned earlier as a leader?

MATT: Oh, man. Yeah, I can see why you would ask that question. Just one thing. One thing that I wish I would have learned earlier.

CLAIRE: It can be several too. We got time. We can get into it.

MATT: When you start a company, you may not necessarily intend to start a company. Sometimes, it just happens through the opportunities. My story is I was participating in the Drupal community. There were maybe 30 developers, not the 3000 or 30,000 developers that there are today. And I was just doing what I love to do, which was to write code with really cool group of people. And the phone kept ringing, people wanting to do paid work and stuff. And so, I sort of begrudgingly started a company and I did that because I wanted to hire my friends and build software together. And when I first started out, there’s that transition of like, I’m doing the thing that I love right now, but then the business needs a voice, the business needs structure. And so, there’s that reluctance of like, “Okay, now I got to go kind of be the company.” And when I became the company, I felt like my job was to protect people. And I feel like, in hindsight, I may have done that to a fault. And what I mean by that is someone came in, “Oh, you’re a developer now.” Now my job as the company is to take care of everything else for you. And I went through this transition of realizing that and taking care of everything for everyone. I may have limited their ability to do their best work because it’s kind of like working without context. If you don’t know what the business needs, if you don’t know if the business is healthy or not healthy, if you’re trying to shield all of your employees from all of that, all they can do is just that small part of their job, which is good and sort of like a good little soldier kind of way, but bad in sort of knowledge work and allowing people to do their best and allowing them to make decisions by knowing how does the company make money? What is defined as success? What are the company’s KPIs? I sort of wanted to shield them from all of that. I could go on and on, but there was a point where that wasn’t working anymore and our company was in jeopardy, and we made a huge pivot at that point.

CLAIRE: Wow. I’m over here nodding my head because that instinct is so real. It’s so real. I don’t know if it’s the sort of founder psychology. I don’t know if it’s fueled by a fear of what will happen if people have this information. I don’t know if it’s fueled, I’m speaking for myself here, ego and thinking, only I can handle this information. Yeah, it’s such a pervasive, tangible thing that exists. I’m so curious to hear, Matt, about this time that you described where you kind of had the wake up call. What happened? Take us back there. What was going on?

MATT: You know what? What came up for me when you were talking was the idea of feeling like a fraud or the realization that like, “Wow, they really knew what was going on. They would see that the business is more fragile than what it is.” Because when you’re starting off, sometimes you have to talk about lines of credit and building up the reserve and all of that sort of stuff. And you’re like, “I want to shield the company from that,” or, “I want to shield the employees from that.” And yet, they’re also the ones that are out there on the frontlines doing all the work that can help make or break things for the entire organization. So for us, we reached a point where we were running into some cash flow issues and we had to ask the team to take a pay cut. This was early on. That’s never the place you want to be.

CLAIRE: It’s the worst.

MATT: So we did that and people didn’t think we were ever going to reinstate those. They thought it was going to be a permanent thing, and we went through that. We had a team retreat coming up at the time. And I had watched Oprah Winfrey back when she had her television show. And I just happened to catch this show where it was about people that were in bankruptcy and people that were stopping smoking. And the first thing that she had them do when they wanted to make a change was invite all their friends over, invite their family over to their house and tell them like, “I smoke. I’ve smoked for 10 years. I never told you. I’m telling you now because I need your help and I can’t do this without you.” And the first thing we need to do is admit where we’re at. And I thought, “Oh my God, there’s something there.” And so, I read this book called The Great Game of Business. It was by Jack Stack. And that guy, his story is really interesting if you’ve never read it. But he’s sort of one of the pioneers of the open-books management philosophy where you share your income statement, profit and loss statement, balance sheet. You share that with your team because we’re all in it together. And the more they know, the better they can do their job. So I thought, “All right, let’s do this at the retreat.” My CTO had an accounting background, she was an accountant. And so she led an Accounting 101 class at the retreat. We did things where we took a stack of pennies of 100 pennies and each penny was a percent. And we played a guessing game of like, where do you think the costs go in the company? Put 20 pennies over here for admin and general expenses. How many pennies do you think for salary and stuff? And what it did is it started a dialogue. Employees generally think that companies make more money than they do. That for every dollar that a company takes in, 80 cents of it goes to the profits of the company. And so, some of it is just an education of where things are. But what it did is it opened up a really brutal conversation for us which was, “I don’t want to keep living this way of running a company paycheck to paycheck. I don’t like this idea of uneven cash flows and doing a line of credit with the bank and then the bank owns the business. I want to live differently. I don’t know everything to do, but I’ve got some ideas and I need you to help. I need everybody’s voices and brains in this because this is better for all of us.” Nobody left. Like that was the biggest fear. It’s like, I’m putting it all out there. I don’t even know if they’ll just get up and leave or what. But they didn’t. And we set a goal. I like to say intentions over goals, but we set an intention of building up a cash reserve, 10% of our revenue for a year in the bank. And we did it. It took a year, but we did it together. And that opens this whole new world for me of like, “Wow!” I don’t know the diplomatic way to say it other than like, “It’s okay to treat people like adults.” Give them everything, everything that they need to do a kick ass job.


MATT: But there’s a lot of fear. There’s a lot of threat. What if somebody can do a job better than me? Or what if somebody sees a mistake on the profit and loss statement? There’s just all of that stuff to go through. And yet in a distributed company, you can’t micromanage. You can’t drive to everybody’s house and see how they’re doing.

CLAIRE: Yeah, there’s so much I want to ask you about here, Matt, and so much I want to unpack. The first is just the sort of thrust behind your approach in this to begin with, your inspiration from good old Oprah.


CLAIRE: And I say that tongue in cheek. But what she’s modeling or what you described was it’s essentially like the science of organizational change management, which is in order to make a big shift in any company, you have to establish trust. And the number one best way to establish trust is actually to show vulnerability. I may have shared this with you. We ran this big survey last year where we asked people what they thought the most effective ways for building trust was. And the typical things that you would think, like team retreats or even thanking people for a job well done didn’t necessarily build trust. And the number one thing people said was showing vulnerability. That was it. It was admitting your mistakes, showing vulnerability and then following through on the things that you say you’re going to do. So those three things. So what you intuitively felt like would be effective, just sort of by the data is effective when you’re trying to announce a big change, when you’re about to make a big shift. And it’s really counterintuitive for us as leaders and I applaud you for this because that’s terrifying. It is terrifying to, like you said, open yourself up and be like the business might be a lot more fragile than we’re willing to admit it. “Oh, my God. Does that mean people are going to leave or does that mean they’re going to think I’m a bad CEO?” And then you use the word fraud. Like I think there’s such an interesting conflation of like identity that we have with our business and who we are as leaders that sometimes gets in the way of us trying to make the most sound decisions. And I love what you shared, how you moved past that.

One of the things I wanted to ask you. I mean literally there’s like 10 things that I could just dive into here of what you shared. But one of the things that I found very remarkable was, the sharing of we’re going to make this shift, we’re going to become more of an open book transparent company and not just doing that but pairing it with the education piece. And for you, the intention being that the context for which people are operating and how they are doing their jobs is what is going to make us successful. Share a little bit more about your philosophy on that and how you thought about that education piece, and how did you balance sort of that fear of like, are people going to get freaked out? What was the thinking behind them?

MATT: Yeah, there’s any number of ways to go with that. And this is a really fun conversation. This is a stuff that I live and breathe so I really enjoy sharing this too.

CLAIRE: Excellent.

MATT: I mean, teaching is just a part of our DNA. When I learned how to build websites, I ran to the libraries and offered if I could teach free classes because I didn’t have computers to share, if I thought I had found like the golden cup. I wanted to liberate everyone through HTML. But yeah, I mean, the sharing component, it’s interesting. Being a distributed company, sharing actually is easier. I don’t know if people buy into that.

CLAIRE: Tell me more about that.

MATT: It truly is because asynchronous communication is easier. So like if I have a conversation, oftentimes there’ll be meeting notes. I can write, every conversation that I have can have a URL. An audio conversation gets recorded. I write up something, I distribute it broadly. It’s there for when people want to consume it. It’s actually easier for me because everybody is using the same communication tools. I’m not just having a conversation with one person that then I have to go broadcast in a bunch of different places. I can invite everybody to the call. And so, that part I don’t find difficult, the sharing and education part.

CLAIRE: What did you find most challenging about that situation? If the education part, I mean, because that’s the part that quite frankly, I found most novel is that you weren’t just like, “Okay, here are the books. Great.” It’s that you literally, it sounds like people through really thoughtful exercises and practices of like, “Can you guess?” And I found that incredible. So, if that was the easy part, curious what the hard part was.

MATT: I mean, look, I didn’t grow up with a business degree. I went to university, I got a degree, but it wasn’t in that. So when I realized that we needed to know our numbers, it had to start with me and my leadership team. We took a Coursera class for, what was it? Three months. A three-month class that we did, where we had to learn the ins and outs. And so we took a lot of the things that we used from that and shared it with the team and did the same exercises with the team. Because we had hired a CFO, an external CFO at the time and they were telling us about KPIs and all of these things and net present value and all that. I was like, “I give up.” Like I’m tapping out, I can’t do this. Before I hire you, I need to go get smart and I need to go learn all this stuff so that I can be at the, not at the same level, but I need to understand what you’re sharing. And so we all did that and then could engage the team. It does make for better employees. I mean, they are making the decisions. They are trying to choose, like do I spend my time here? Do I spend my time here? How is this project structured? How much value does it have to the organization? And the more that you can include them in those conversations and actually give them a voice, shift that transparency to collaboration in some way, the more it’s like you hired the people that you hired for a reason: to be the professionals that they are at the work that they do, not just to give marching orders. And so the more that you can engage them to do that, engage their brains, the better that they can be.

CLAIRE: Absolutely.

MATT: The big realization that I had is that as leaders, we’re making all of these decisions and have all of these data points in our heads and then all we’re doing is sharing the end result or the conclusions with our team. And that sucks, man. That sucks to be like, stand on high and say, “I have decreed that we will do this and not this and this.” And they’re just like, “Uh, I got a question.” “Yeah.” “Why? Why are you doing this?” And like, “Why didn’t you bring us into the conversation earlier?” And so around that time that we were running into problems, I also had this thing of like, I want to value my job not just on how profitable the company is or not just on how well the employees are doing or the clients we have. I really want to try and do this thing. I want to see if I can align the goals of the company with that of the team. In other words, what if we all were going in the same direction? Why does it have to be this curtain here where the company has all these things going on and the team doesn’t. What if we’re all going the same place in the same way for all the things? God, that just seems clean and a lot less stress on my head in needing to keep everything separate and the answer to different voices and all that.

CLAIRE: I’m smiling over here Matt, because what you have described is sort of the seminal management scholars of our time have proven out to be true in terms of effective and high performing teams. If you even look at, there’s this wonderful scholar whose name is Edward Nietzsche, and he spent 20 plus years studying human motivation. And he talks about how the way for people to actually do their best work is not for it to be an extrinsic motivation. So someone telling them to do, or a fear or a threat or a reward, but it’s for them to be intrinsically motivated. And the only way to do that is to really align with what it is that they want. And it’s the big challenge that so many companies and organizations have. So I love that. Like you have this, I mean, you’ve spent over a decade doing this, trying to figure out how do you align that team up, how do you get to that place?

MATT: And that intrinsic motivation, that’s cool. I hadn’t heard of that, but that’s awesome. That intrinsic motivation, the reason to tap into that is because then people start to share gifts with you that otherwise aren’t accessible. I’m talking about passion, like that’s the way to passion. You can’t ask somebody to be passionate, like they have to want it. That’s the source, that intrinsic motivation. I want to do this because it feels good to me. I want to share my passion with this team, with these people.

CLAIRE: And what’s fascinating is that people all have it. They don’t always show it, but they all have it. And we as leaders and the structures we’ve created in our company, sometimes or oftentimes drown that out. So it’s within every single person. And there are so many studies that have been done that when people are actually, it’s fascinating, whether it’s kids or adults, school, classrooms or in companies, when people are doing things because they truly believe that it’s something that they want to do versus someone else or out of fear or for a reward, they perform better. So the outcome is actually better. They learn more and they actually enjoy the process more too. And that’s always intrinsic motivation to your point. I think the hard thing is because I think a lot of folks who’d be listening to this will go, “Yeah, totally. I’m with you, Matt. I’m with you, Claire.” How? There’s stuff in the company that has to get done that someone has to do. There’s things that are hard. There are things that, “Hell, I have to do, as the leader,” or that, “They don’t fall into my passion.” How do you do this? How do you tap into people’s intrinsic motivation? Or how do you try to create that alignment between self and team, and team and organization?

MATT: Whenever I get uncomfortable, I’ve learned to lead with authenticity. And it’s hard. It’s like, “Well, be vulnerable.” It’s real easy. But in my experience, if you’re vulnerable, by sharing your vulnerability, by being authentic about it, you sort of take the vulnerability away. There’s a moment where you become human and you trade that vulnerability for hopefully earning trust.


MATT: And so, what it does is it’s the start of a dialogue. The other thing that comes to mind is just like, it’s just getting out of the way sometimes. Leaders are often doers of like, “Okay, there’s a problem. I’ve got to fix the problem.” And so having that, taking that step, it’s a little bit cliche, but taking that step back and say, “How do you think we should solve it? What do you think we should do?” And allowing people to put their brains and voices and passion into the problem rather than solving it for them. Reminding yourself, “I hired this person for a reason.” They are at the forefront of this. They are our marketing person. If anybody knows the answer, it’s going to be them. And then my job is to give them the tools and the resources and the guidance that they need.

CLAIRE: Absolutely. Yeah, you were saying, if anyone knows the answer, they’re going to be the ones who know. It’s so sort of reinforcing to so many other conversations that I’ve had with other executives and CEOs. You might know Wade Foster who runs Zapier. We’ve had him and we’ve had Michael Lopp who’s the VP of Engineering over at Slack on the show too. And they both have talked about something really similarly about, one, the best managers don’t solve problems themselves. They let their team solve the problems that they hired them to do. And then Michael Lopp has talked a lot about how the best leaders aren’t busy. And it’s about, to your point, holding space, creating space for people to figure things out on their own. Someone can’t be intrinsically motivated to figure something out if you don’t give them the space to do that. And so, I so appreciate that reinforcement. And to your point, it also requires authenticity and some vulnerability to give that up and say, “Alright, I’m going to back off. I don’t have all the answers. I’m not the decision maker here.”

I’m wondering, Matt, you talked a lot about vulnerability, about building trust. In a remote team in particular, there are so many executives, CEOs, and managers that I’ve talked with who’ve shared and admitted that building trust in a remote team is particularly challenging in their opinion. You’re not face to face, you maybe have folks coming in from a lot of different countries, different even geographies within the United States. Like that always adds to a feeling even of distance in a company. I’m curious what your experience with building trust within a remote company has been throughout the years, how it’s changed, how you think about it at Lullabot, and what you feel like you’ve done really well on this, and maybe some of the mistakes you’ve made along the way too.

MATT: That’s a great question. Maybe a place to sort of start is by an admission that you have physical companies that have their ways of doing things in person. All hands on deck meetings and stuff like that. You have remote companies that grew up with processes and systems. Any of those companies in the middle that have some remote and some physical, those are the hardest companies because everybody’s using different communication systems. Those are the companies that are going to struggle the most with this kind of a general question because it’s Sally’s birthday and there’s birthday cake in the kitchen office. The mass email goes out to all the employees, 50% aren’t there. They’re remote employees. And so, they don’t get the birthday cake. And so, like that is a really tough problem to solve. As a remote company though, it’s sort of the same as a physical company. You get to pick the same tools that everybody uses. You do have time zone differences which you need to take into account. And one of the ways that — we’ve tried to hire 12-hour time zone differences and things like that. And candidly, it hasn’t worked for us. We’ve found that a nine-hour time difference at the most is the most that we can do. Six hours for us from a US Eastern time is as far as we’ll go in the hiring process because we’ve got to have some overlap.

CLAIRE: Super interesting. Is that because frequency of touch point is you think so integral to that sense of connection?

MATT: Yeah. Because like, say you’re in Spain. You can work a noon to eight over there and get sort of that nine to five overlap more or less in the US Eastern time. And so there’s enough touchpoints in there. And because we do client services work and most of our clients are in the US, we’ve got to have some overlap there. But we have town halls once a month where everybody comes on and they type their questions in Slack. Any question is fine for the leadership team. And then we answer those questions. We have silly, fun things that we do that are really, really important because it’s the equivalent of going and catching a football game on the weekend or things like that.

CLAIRE: What’s an example?

MATT: One is we have a serendipity call that’s half an hour every Friday morning. Just sort of like, “Hey, it’s Friday.” We’ve got this long document that the whole team has contributed to about silly questions. First book that you read, first type of car, one thing that you’re scared of that nobody knows, or awkward haircut photo, whatever it is. And we have a script that puts people into groups, random groups of five and they just talk for half an hour. And the question is sort of like an ice breaker question. But otherwise it’s, “Hey, how was your week? What are you planning to do this weekend?” And it’s really important. It’s just sort of like, “Ah…” I never get to talk to this person and get to hear them. It’s not about work. That kind of thing. And so we do it. We do a team call, too, every Monday morning, the whole company. Almost 60 of us jump on the phone and we have a little script that keeps track of who’s talked and who hasn’t talked. And so each person gets two minutes and then the leadership team gives an update at the end. Just bringing those people together, the Slack channels you have are important too, a mental health Slack channel, a dog Slack channel, a cat Slack channel. all of that kind of stuff too is really, really important. Have fun. You got to remember to have fun. And with a distributed company, you need to be more intentional about it.

CLAIRE: Yes, absolutely. That is definitely the consistent feedback. I mean, even for us as a remote company ourselves, we think a lot — I mean, even for being so small. But we have to think intentionally. I always think, if we were co-located, I would have sort of defaulted to being a lot less intentional about social interaction or about connection. But being remote, we really have to sort of systematize it and really think about it a lot more thoroughly, even being so small. One thing caught my attention with what you said, you talked about a mental health Slack channel. Actually, I was reading a blog, the Lullabot blog the other day and you wrote a post about how you’re doing what sounded like a mental health initiative and it was something that you talked about during the last retreat. I would love to hear more about where this came from and why this is of any importance to you as a CEO and as a leader.

MATT: Yeah. I got a little emotional about this one. There’s the light and there’s a shadow is about being the remote company. Everybody likes to talk about like, there’s that whole, I don’t know, like sort of like influencer. Like, “Look, I’m in a Mongolian ger.

CLAIRE: Digital nomad.

MATT: Yeah, that stuff. You can do those things, but that comes with its own fear and anxieties as well of like not knowing where you’re going to work the next day.

The shadows of remote work is isolation, depression. Somebody may be going through something really difficult and you don’t even know because you’re just getting this text every now and then from them. And so, our jobs is not to pretend that everything’s okay all the time. It’s to sort of be a little bit anxious about what are the places that could sort of seep into our organization that could hurt us. I was just really feeling that one day. And so, I wrote up this thing on my internal company blog and I just said, “Hey, we’ve been fortunate that we haven’t had to deal with this. But I fear that this is an area that we need to improve on.” And there’s this one guy in particular, JD Flynn, who’s an awesome human being. I saw him give a talk about mental health and open source software and all of that. And I was just totally moved by what he said. And so I said, “Well, what do you do with anything else?” You start talking about it and you just start putting it out. And so I put a message out to my team and I said, “Does anybody want to talk about this with me and figure out what we could do, what’s lacking, how we could improve? And so we just started a dialogue. And we sent a survey out to the team and said like, Where are we dropping the ball on this?” People got back like, “I’ve tried to hire a therapist, but I can’t figure out our insurance. The insurance costs are too expensive. I feel like I can’t talk to my manager about this because I’m going to get judged.” And so we’re still having these meetings and figuring out things to do. But yeah, we call it submarining is the name that we use when somebody goes dark for a while and we haven’t heard from them. And so we want to make sure that our managers are empowered to know what to do and how to reach out and how to give support and all of those things. But yeah, you got to stay present in a distributed company and have ways on how to do that.

CLAIRE: I think that’s incredible. And it’s interesting sort of when you look at the numbers of actual depression and loneliness in the workplace, it actually isn’t any more prevalent [inaudible] numbers in remote workplaces as it is in physical spaces.

MATT: One in five, right? One in five, one in four.

CLAIRE: Yeah, exactly. It’s like oddly similar. I think sort of the assumption would be like, “Oh, definitely if you’re in a remote company, the tendency to experience that might be higher.” But what I find fascinating is we live in this new work environment where you may be a co-located company but you’re just talking to all your teammates in Slack all day and maybe they never see your face. And there’s something about the sensitivity that we have to have as leaders to this because, I mean, how many studies are there about just how loneliness and lack of social interaction affect just lifespan? Thinking about work performance. Forget about work performance but lifespan, right? And so, the approach that you’re taking to this I think is so refreshing and so in-line with your whole philosophy for how you think about pretty much everything as a leader of being open, talking about it and having the conversation. I also find so remarkable that you’ve created this environment where you actually have team members admitting to you that they don’t feel comfortable talking to their manager about it and are willing to be so open. I think some leaders who might be listening to this, their fear is radio silence.

MATT: Yeah. Can we lean into that for a moment?


MATT: The closing thought on the mental health thing is I’ve also found that people that work by themselves at home are people that, you need to empower them to be proactive about the energy that they need to recharge. I had one person, for instance, she never bought coffee because her way of staying sort of vibrant and engaged was leaving her house, having a reason to leave her house to go get coffee. That was her way of making sure that she got out at least once a day, interacted with her friends at the cafe or whatever and did that. So oftentimes people that live with other people or have families and stuff, they’ve got enough social interaction generally speaking, but that’s just been my experience on that. Two principles have been really important to me. One is aligning the company goals with the team goals. That’s been one thing. The other thing you just talked about, which was psychological safety, which is kind of a wild concept. There was a woman, I don’t remember her name right now, but she really advocated for this. She gave a TED talk.

CLAIRE: Amy Edmondson?

MATT: Thank you, yeah. And she said, “You will not be punished or humiliated for speaking up with questions, thoughts or concerns.” I said, “Oh man, that’s wow.” On the surface, it sounds so easy. So I started to put it into practice. It’s hard. No, it’s not easy.

CLAIRE: It’s so hard. [Laughs]

MATT: No, I want to take everything personally. I’d be offended by everything that comes up and just say, “You know what, Claire, I’m going to make a safe space for you. Tell me, how do you really feel about things?” And my obligation to you is to keep that space safe. It’s not easy to do.

CLAIRE: It’s so challenging. It’s so funny because we run workshops on this stuff. I do this stuff for a living and even in my day to day practice as a CEO, I find the line of setting a tone of psychological safety and yet at the same time, wanting to maintain a standard of here’s how things in the company should run and here’s kind of what I want an opinion of myself and of the team to be. They’re not always like in conflict with each other, but sometimes it’s hard to have them in concert with one another. It’s hard for them to co-exist. And so it’s to your point, it’s such a hard thing to do in practice.

MATT: Right. And yet it starts with us. If we’re not modeling the behavior, nobody else is going to. And in those critical moments, everybody is looking to us to see how we respond.

CLAIRE: Exactly.

MATT: But it’s also been great. You ask how do you get people to surface things about mental health and how the company’s really doing? You got to make it a safe space. It’s a process. It’s a journey to get there.

CLAIRE: Matt, I know so many people who are listening to this podcast are going to be looking to you in terms of how they’re thinking about leadership. This has been absolutely incredible. I have one last sort of burning question before we get off here, and I truly could talk to you for hours and so I’m just trying to cut myself off here preemptively. You’ve been running a remote company for a good, it’s been what?

MATT: Thirteen years.

CLAIRE: Yeah, exactly. I mean before sort of the idea in many ways of running a remote company has been in vogue and hot, et cetera, and I’m sure you’ve sort of seen the sentiment of it being something of, “Oh, what do you mean you’re remote?’ To now being popular. Really interesting. What’s your biggest pet peeve when people ask you about a remote company or you hear someone who’s trying to become a remote company or just like a thing that you hear a lot from other CEOs and managers when talking about remote companies where you’re like, “You know what, I want to set the record straight.” Or, “You know what, that’s not true.” For us, we actually have found this to work. Curious if there’s been anything of that nature.

MATT: That’s really interesting. I think that probably the biggest stereotype to bust on that one is that remote companies don’t communicate. And I would argue that they communicate, they have the potential to communicate better than physical companies. I think I said earlier that you can give every piece of kind of communication that you have – a URL, a link, it can be recorded, it can be written. Oftentimes for remote companies to be their best, I’m going to go on record to say rely on written communication. And in order to write, you have to kind of know yourself. You have to find that quiet to search for your words. You’re not just spewing spontaneous things in a meeting. There is a place for that, the strategy brainstorming conversations, but not when it comes to policy and purpose and all those other things that we need to do as leaders. So to actually sit down with thought, with intention to write, it becomes like carving stones like tablets that are like canonical resources for your team to know where things are. And you can have great communication where everybody feels aligned and tapped in. And part of that is just you get to use all those fancy digital tools at your disposal to broadcast your messages.

CLAIRE: Oh, completely. I will go on record to say, Matt, that I completely agree with you. I’ve found it so interesting how the lack of sort of reflexive communication, in person communication becomes a forcing function for much more intentional and thoughtful communication. It’s like you have to put more energy into it because it’s not as easy just by default. And as a result, it gets better because of that. So thank you so much for sharing that wisdom and for all the wisdom that you’ve shared. My goodness, there’s so many things that I took away and I know for everyone who’s listening as well. And so, thank you to everyone who’s listening. If you enjoyed this interview with Matt and I, definitely be sure to rate our podcast on iTunes. And Matt, thank you so much again for your time.

MATT: Thank you, Claire. I had a great time.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.