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Episode 41: Interview with Nick Francis, CEO and Co-Founder of Help Scout

As the CEO and Co-Founder of Help Scout, Nick Francis talks about being self-aware of all the things that you don’t know as a leader, hiring people in a remote culture, having and recognizing your own flaws, and that the real measure of a good leader is what happens when you’re not around.

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 Nick Francis, the CEO and Co-Founder of Help Scout.

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CLAIRE: Hi, everyone. I’m Claire Lew. I’m the CEO of Know Your Team: software that helps managers avoid becoming a bad boss.

And I have someone who is possibly the most opposite person of a bad boss who I’ve admired and respected for a very long time. I’ve got with me today Nick Francis who is the CEO and Co-founder of Help Scout, an amazing customer support platform that we actually, at Know Your Team, use and we’ve been customers for years – very, very happy customers. I originally got to know Nick, obviously, in him being a wonderful customer. But their company is pretty incredible, entirely remote, has over 90 employees, serving close to 10000, if not more than 10000 customers. By the hour, by the end of this call, it’ll be more than that. And I’m so excited to chat with you today, Nick, because I followed your writing. I had like a million questions from some blog posts that you’ve written. So, we have no shortage of things to talk about. But the first question I did want to ask you is around leadership.

Actually, before I ask you that, there was actually one other thing I did want to ask you about, which is, you were sort of hinting to me that there was something really fun that you guys were doing with the company. And so, I want to ask you about that. And then we’ll get to the meat of things.

NICK: OK, no problem. You may know this, you may not, but in February, Help Scout became a Certified B corporation. It’s something that we worked on for more than a year, and we’re really proud of the certification, really proud to be part of that community. And as a result of that, we started a program that’s in the process. In the next month or so, we’ll launch it and talk about it but it’s called Help Scout for Good. There’s a number of things that we’re going to do under the umbrella of Help Scout for Good. But one of those is that we’re doubling our discount for nonprofits to 20%. We’re also offering a 20% discount to all Certified B corps. And then finally, we’re offering up to a 100% discount to certain organizations that support some issues that we care deeply about – human rights, the environment, and online security and privacy. So yeah, we’re excited about that program and I’m trying to tell as many people as possible about it. So, Help Scout for Good.

CLAIRE: Help Scout for Good, you heard it here first, really nice. Incredible.

NICK: Really first, I haven’t talked about it.


CLAIRE: I’m actually really honored. Actually, truly first, everyone who’s listening to this. That’s amazing and so in line with your mission and not to give everything away, I feel like it is just from knowing you, it’s so in line with your own personal leadership philosophy. So, let’s start around there. Here’s the one question around leadership that I’ve been asking folks, Nick, which is what’s something, or there could be several things, it doesn’t have to be one thing, that you wish you would’ve learned earlier as a leader?

NICK: I have to constantly remind myself of all the things that I don’t know. As an entrepreneur, you have this sort of built-in ego and self-confidence, and that can be a really positive thing. It’s almost necessary for an entrepreneur. But at the same time, it’s really important to be really self-aware of all the things that you don’t know. Even if you feel like an expert, there’s a lot of things that you don’t know about the work, about other people, about interacting with other people. And so most definitely, the number one thing that I strive for, as a CEO, is greater self-awareness on a daily basis. I think that’s the most important thing for me to just sort of keep my ego in check and to really focus on leveraging it for a lot of the good things that it can do for our company. That’s certainly something that I think about a lot.

CLAIRE: I love that just because it’s so interesting. You ask academic scholars about leadership to define what makes a good leader and there’s this wonderful quote about how. There are about as many definitions of leadership and of good leadership as there are people who have tried to define it. So point being, it’s kind of all over the place. However, I will say the most consistent thread that I’ve heard around the definition of good leadership is actually what you described. This ability to see things for what they are instead of what you would like them to be, the ability to not put your own self-interest first but this group of individuals who you’re sort of representing. I’m wondering, when in your journey, whether it was as CEO of Help Scout or maybe it was earlier, did you realize this? Because I don’t think it is an obvious insight until you are in the role. Do you remember if there was a specific time or was there a series of events?

NICK: There’s probably a series of events. I can talk about a few of them. We’ve brought on some — well, before I get to the good one. In the first two years of the company, most people don’t know this, but in the first two years of the company, we fired 40% of the people we hired. It was a complete circus. We made a lot of mistakes. And the three founders, myself included, had never hired anybody before. When we started this company, we knew how to build stuff. We knew how to make stuff but we didn’t really know how to build a team, much less a remote team, with a specific culture and ethos that we had in mind. And so, we made a bunch of mistakes along those lines. And there’s nothing like failure to bring about self-awareness.


CLAIRE: Oh, my gosh! Yeah.

NICK: So that’s what I mean. But we did finally figure out how to hire great people that aligned with our ethos and made our company even better. And there’s particular people in my sphere, one that comes to mind is Becca. She runs people ops for our team and she has been a constant source of not only compassion and friendship but of accountability with regard to interpersonal relationships on the team, how I’m conducting myself, facing my demons which she’s made me well aware of, alongside other people.

CLAIRE: She calls you out, huh?

NICK: Yeah. So, you really need a source of accountability within the company. I’m not talking about a board level accountability. I’m not talking about customer level accountability. I’m talking about people in the company that can really call you out and challenge you to be the best version of yourself.

CLAIRE: That’s invaluable, I think, and so rare.

NICK: Don’t tell Becca she’s invaluable, though. Be careful.


NICK: Just joking. She totally is.

CLAIRE: We won’t make that public. I want to go back to this. In the beginning years of the company, firing 40% of the company. I’m like, “Oh man, that is hard.” I’m wondering what things you now think about in terms of hiring. And then also it’s sort of a two part question. To this point about accountability within the company, is that something you actually actively look for and hire for or was that sort of unintentional and then you realized, “Oh, this is now really important. We should hire for this.” So, kind of both things: like lessons learned around hiring, best practices, especially as a remote company. I know you’ve written about this. You have a wonderful post, I think it was back in 2016 where you wrote about the differences of hiring between remote and in-person. That’s phenomenal and I highly recommend folks to check that out on the Help Scout blog, I believe. But yeah, I just want to sort of pick your brain around hiring in particular.

NICK: One of the important things about building a remote culture is that you do have to be able to do the work with a certain level of autonomy and skill. One of the big mistakes that we sort of made early on is hiring people that weren’t — I hate saying junior or senior level, but they hadn’t been doing the craft for a very long time. They were maybe right out of school or they were just figuring out what they wanted to do in their career. They were just in a different place. And I found that in remote, you really want to, first of all, hire and recruit people that are in love with the work. Culture is a piece of it, but they really need to love the work and they need to be able to accomplish a lot.

If they’re sitting in a room by themselves for an eight-hour day, they still need to be able to get a lot done. And I’m not saying that’s how it is at Help Scout. I spent a lot of my time, most of my time talking with people as you and I are talking now, but still, you want people to be capable of doing great things in a self-sufficient way. I think a lot of companies would say that they want that, but you have to dial that up in a remote culture. It’s a requirement. It’s not something that you hope for. A culture of mentorship is really difficult to execute against in a remote culture. We sort of wave the white flag on that one and decided that’s not our culture. Our culture is one. And if we want to hire the highest performers, people that are better than us, to make the company better. That’s a different thing to look for. And so, I can talk about some of the tactics and the ways that we look for that in the hiring process and we fix some of the mistakes. But generally, you just want to look for a different profile based on the remote nature of our culture.

CLAIRE: Absolutely. You are definitely not the only person and CEO to say that. You have quite a large remote team. I interviewed Wade Foster from Zapier and Joel Gascoigne from Buffer, and they very similarly, actually very honestly described — and actually for us, we’re a very, very small remote company and we have the double challenge of being really small and remote. So, we can’t, unfortunately, afford to hire one who’s “junior”, whatever that means. But what it really means to your point is just someone who’s just had some time and experience working on their own and actually working on the work itself. And what they both admitted to me, I actually remember Wade in particular, that he hasn’t quite figured out yet. And I wonder if you would agree with this, is that unfortunately it means that it’s actually really higher to hire for potential which sometimes can be a wonderful surprise. It also means you can’t grow people maybe as naturally or as organically as in an in-person company. Would you argue with that? Would you say you sort of put some things in place at Help Scout to try to account for that? Just curious to get your opinion on that side of things.

NICK: Wade’s totally right. Joel’s totally right. We talk about these things. The three of us all the time. [Chuckles]

CLAIRE: [Laughs] I’m sure.

NICK: I really admire what both of those CEOs are doing. Yeah, Wade’s totally right. It’s really difficult to hire for potential especially in a remote culture because to some extent, eventually no matter how much on-boarding you go through, you’re going to get kind of thrown into the deep end and we’re going to ask you to swim. And that’s really hard to avoid as a remote culture. And so, I’ve just found that one way to test for that in the hiring process is using projects. One thing that’s just different about hiring — so, I spent six years in Boston before I moved to Boulder. In those six years in Boston, I saw most of the companies, they’re co-located, and I saw how different their hiring process is. You go from beginning to end, offer letter, 10 days.


NICK: Sometimes, even shorter.

I mean, people move really fast to hire people in co-located culture. Whereas in a remote culture, our average time to hire is between 30 and 40 days. We really get to know the person. And I think that actually helps both sides. We talk with a lot of people that we interview, whether it worked out or not, about the hiring process just to get feedback. And they really like the fact that they’re able to get to know some folks, they’re able to work remotely a little bit by way of doing a project.

And so, we do give everybody a project. It takes anywhere from four to eight hours, depending on the role that we’re hiring for and some other variables. And we actually just work with them. We give them feedback. We may do a couple of rounds, going back and forth, but it’s really important that they not only be able to talk well about themselves but they be able to execute on work that we give them. And so, that’s one way you can solve that potential challenge that Wade talks about. And by way of having 30 to 40 days to work through that process with a candidate, it just kind of frees you up to really go deep and determine whether it’s a fit on both sides.

CLAIRE: Absolutely. And I don’t think that that advice is actually unique to remote companies. What you learn, I mean, even in working with someone for first four to eight hours, it’s incredible. A lot of the times, when we actually — and we’re in the process right now of hiring and one of the candidates we’ve worked with actually for the past few months. And it’s like that in itself, it’s kind of the best reference call/resume you’ll ever need. Like that’s just the proof in itself. So, I think for folks who are watching this and listening to this, whether or not you run a remote team, to take that to heart.

Speaking of a remote team, and you’ve written extensively on this topic, Nick. I know it’s so sort of, I don’t want to say it’s clichÈ, but it’s popular right now to talk about best practices in a remote team, obviously very important, and we can talk about that except the first thing I want to talk about is actually something a little bit counterintuitive that you published, I think, earlier this year about working in a remote team. I believe the phrase — I wrote it down — you said, “Overdoing asynchronous communication.” I want to dig into this because I was like, “Oh! This is so interesting.” For those of you who are remote leaders who are watching this or you work in a remote company, that sort of the tendency is you have two forms of communication – communicating sort of in person, rapid fire in Slack or Basecamp or whatever, all the time chat back and forth, or there’s asynchronous long form, you do it on your own time. And most companies tend to default towards synchronous. And so, it was interesting, your post talked about going too far on the asynchronous side and actually how that was harmful. So, tell me a little bit about that. What was going on?

NICK: The difference between co-located cultures and remote cultures is, the way I like to describe it is it’s just a series of tradeoffs, both of which can be really successful but there’s a series of tradeoffs. For instance, co-located culture, synchronous communication is the default. Whereas asynchronous communication is more of the default in a remote company. It’s not intuitive to be like, “Oh, let me call up my teammate and have a video chat with him about something.” You actually have to think about it, whereas it may be more intuitive to shoot them a chat, a message, email, or whatever. And so, it’s really important to understand a number of those tradeoffs just eyes wide open, going in, knowing what you’re going to have to optimize for.

And so, when the default is asynchronous communication and your team intuitively works that way, you can most definitely go too far with that. I had noticed a trend over the last year or so is when I started to understand. But it took us longer to solve hard problems because we were back and forth doing common threads and a doc or something like that. I actually picked up on one of our retreats, I saw a few engineers around the table and they had solved an issue in a matter of two or three hours that had really been plaguing them for a number of weeks. I just found that, “Wow! That’s just really magic.” And look, video gives you 98% of fidelity that you get sitting around a table. And so, that’s one example. But I could give you a number of examples where if as a team, we can just coach everybody to lean into face-to-face communication, that high fidelity synchronous communication. I know it’s a little counterintuitive on a remote culture but you can just move faster. You can, I almost said the word ‘synergize’, but you can really build a relationship face-to-face in a way that is not possible in Slack or email or anything like that. And so, relationship building is such an important thing that you have to over optimize for in a remote culture. So, leaning into to a lot of the face-to-face synchronous stuff is just important. And I don’t think enough remote companies talk about that aspect of it. They just assume the entire business runs asynchronously. At least in our case, we found that maybe 20% of the time, conducting your self in actual meetings and face-to-face video chats and stuff is a really productive way of working.

CLAIRE: I so appreciate the nuance. I think that’s what I found so refreshing about the piece is that it wasn’t — I mean, I just think it’s so easy to — and you sort of see it in kind of the blog posts and tweets and things that come out around a remote work. It’s so easy to be dogmatic about like, “Oh, we play for remote teams,” or, “We play on the co-located.” And it’s just like you said, it’s a series of tradeoffs. One is not right or another, and you have to sort of operate across a sliding scale instead of saying, “Oh, we have to go 100% on asynchronous,” or, “We can go 100% on synchronous.” So, I think that’s such a good important insight.

NICK: It feels like sacrilege to be like, “Oh, face-to-face communication is actually pretty awesome and getting around the table to work through a problem can be really helpful.” It almost feels like we’re breaking some unwritten rule of remote culture that we’re not supposed to talk about. I just think it’s great and we’ve got great tools these days that we can leverage to have face-to-face communication all over the planet. So, why don’t we talk about it more? That’s all.

CLAIRE: Right, and I agree that there’s some sort of mix. So, in terms of sort of Help Scout’s culture as a whole, I know it’s something that you think a lot intentionally, you write a lot intentionally about. What do you think has been the real cornerstone in helping the culture be what it is today. As you reflect on Help Scout’s journey and go, “Gosh, I’m so glad we did A. We could have done a lot of other things wrong or done a lot of things different. But as long as we did A or B or whatever that few things are that you feel like helped solidify Help Scout’s culture or continues to. What that might be?

NICK: There’s a shift early on in a company when you go from founders working in a room together to founders also working alongside people that you hire to then the people that you hire hiring people to be part of your team. And at some point, you have to codify what your values are because the founders aren’t hiring everybody.

There was a point maybe two or three years into the company where, I think it was Becca who we’ve already talked about, she did this research project where she asked everybody on the team. She interviewed everybody on the team about what makes Help Scout really great, what’s important to them about the culture and just did this big values exercise where we actually wanted to codify our values. She didn’t interview the founders. She interviewed all the team members we had at the time and picked up on a bunch of phrases and keywords that seemed to be sort of a trend, and then kind of sent us a document. And we decided on what our core values would be, very thoughtfully and very intentionally. It’s important to note that they were informed by not us but our team, the team that we had crafted up to that point. And by way of writing down the values and talking about them in a way where it became part of our vocabulary and part of our ongoing — we didn’t put up posters in the office or anything. We just started to talk about them more often. And by way of doing that, I think it really manifested the ethos that we wanted to see the company have and it was way beyond what the founders were capable of building themselves. I mean, I talk a lot about hiring people that are better than us. Sometimes, that can rub people the wrong way. But I think the three of us, founders, most definitely agree that we’ve hired a bunch of people that are much better than us at various things and that certainly applies to the values and the ethos. I would love to say that I’m as pure and as sort of untainted as the Help Scout values but I’m not.

CLAIRE: You’re fallible, Nick? What? You make mistakes?

NICK: I have flaws. I make mistakes but the way that we talked about Help Scout and the way that we, to some extent, really set ourselves up for a much higher level of critique publicly, it’s those values then that form that brand. And we’re happy to hold ourselves to a super high standard in that regard and that’s way beyond what we could have initially kind of done or manifested in the company as founders. And so, just finding a way to codify those values was a really important turning point for us.

CLAIRE: Absolutely. That’s such an interesting response because I think maybe for people who are listening to this, Nick, they might be like, “Oh, yeah.” Somewhat obvious, maybe. But I think your approach is actually quite unique in that it wasn’t you sort of leading a brainstorm session. It wasn’t like a piece of paper that was sort of put forward saying, “Here is the list of the 10 words. Choose six.” You weren’t even involved in the process. And talk about actually maybe being a little nerve-racking, I can only imagine as someone starting the company and then being like, “OK, now I’m having all these other people,” sort of defines the heart and soul of it.

NICK: Didn’t seem really necessary to me. I was like, “Do we really need to write? Are we going to be that company that writes down their core values and sings Kumbaya and gets in a circle?” But it was totally led by Becca and she was right on with her instincts in wanting to write them down at that point. You’re totally right. The fact that it wasn’t really led by us. The fact that it was somewhat of a nuisance initially made the process that much more organic and productive.

CLAIRE: Totally. And I think also for a lot of leaders, you’re like, “When do we have the time to do that?” Or like, on the list of priority, where does this fit in with sort of product strategy and hiring and recruiting. And it’s like, “Oh, we’re going to do a values exercise? Really?” What would you say to a leader right now who’s, let’s say, sitting across from you, and he’s like, “I don’t know, Nick,” like a little skeptical, “Is that really it?”

NICK: Something popped into my head which was a really big remote running that nobody’s talked about which is that early on in the company, we really over-invested in what we call people ops, formerly known as HR, I guess. We really invested heavily into the people ops function. And we have that to thank for codifying our values. But a bunch of other things, as well. I believe when we were 17, 18 people, we had three in people ops that were…

CLAIRE: That is a lot.

NICK: Yeah, cultivating this culture and this ethos. And not only that, but setting us up to do proactive recruiting of candidates that would help us even out the hiring pool with underrepresented groups. And so, by over-investing, on paper, that would never make any sense.

There’s not a CEO on the planet that would see three people, ops people of 18 and think that’s a good idea. But in a remote culture — and it just sort of turned out that way, we hired a couple of people that ended up just gravitating towards that field. But that became such a critical thing for us in order to sustain these values and build this culture that everybody’s pretty proud of now.

Early on, especially if your team is remote, I think when you’re remote, you have to solve a lot of scaling challenges way before co-located companies have to solve them. And that was one of them, just getting the culture in hiring process and all of these things dial because they’re all a reflection of the brand. And that’s our most valuable asset. And so, when it comes to codifying values or figuring out your hiring process, figuring out how to make remote work, all of that revolves around the people ops function which if you overinvest in early on, I think you would look back in hindsight and never ever regret it.

CLAIRE: Counterintuitive, really.

NICK: Well, everybody wants to invest in the product, right? Like build sales, marketing product.

CLAIRE: Totally.

NICK: But it’s not just about that. It depends on the kind of business you’re building. But we want to build a business that is still going to be able to sustain itself for the long term. And so, you have to get the fundamentals right. Product comes and goes.

CLAIRE: Right. And what influences product? It’s people.

NICK: Right.

CLAIRE: It’s the environment they’re working on. It’s on how well people are communicating. It’s on if they feel valued. I’m thinking to myself, “Oh, that’s something I’m definitely taking away from this conversation,” because I think somehow I would have heard those numbers when we were that size and I would’ve been like, “Really? Really? Interesting.” It’s amazing. It explains a lot, to be frank, about now knowing and seeing the success of your company and firsthand, knowing the kind of culture that you have.

NICK: The reason we decided to build a remote culture was all about talent. Selfishly, it wasn’t that I wanted to live all over the world and be a journeyman. It wasn’t anything about my own quality of life because frankly, I felt like we needed to have a better team, a more talented group of individuals as part of our company in order to survive in a really crowded market. We’re in the world’s largest software market – CRM.

CLAIRE: Yes, you are.

NICK: It’s not going away, lots of competitors. And in order to gain some sort of advantage, I felt like talent was going to be critical for us. If you want to hire great people that really do make the company better, it does start with the company and the culture that they’re working for. And so, again, with overinvesting in people ops, I just feel like we were setting a foundation upon which we could build a remote sort of brand. My goal was always to be in the top five companies that somebody thought of when they’re ready to get a remote job. And if we were there, I felt like we would be exposed to a level of talent that would help us stand out in the market.

CLAIRE: Absolutely. Thank you for sharing that.

NICK: Yeah. Just to tie it all back to revenue… I’m not all Kumbaya if you want to build a great business.

CLAIRE: I mean, I don’t know. The Kumbaya is good too because I think we — I will speak for myself. I got into this world to build a business, yes, to make a ton of money, yes, to help a lot of people. And then obviously, to, as well, build a place like you said, that people want to work at. And there’s a feeling of definitely satisfaction and reward that comes with it. If you kind of scoop it all and cover it all, that is the goal. Nick, you took a sabbatical recently?

NICK: I did. Yeah. I took a month off for the first time in eight years.


NICK: It was really great.

CLAIRE: I loved the piece that you wrote about it. It was so interesting. I would love for you to share with folks who are tuning in, going into this, sort of, why did you take it? How were you feeling? Were you sort of nervous? Was this like a reluctant sabbatical? Or are you just sort of like running into it like, “Yes! I need this after eight years.”

NICK: Yeah. I take vacations and stuff but I always typically work a couple of hours a day on vacation just to kind of keep up with things. I’ve been a dependency for a really long time in a number of areas of the business, so I felt like even when I go on vacation, I’m going to have to — I can count on my one hand the number of days I’ve spent completely off grid at Help Scout, at least pre-sabbatical.

I got to the point where I felt like that was no longer healthy for the business, for me to be glue in so many areas for the company to sort of struggle without my input or without me adding some sort of value to the equation. And so, I also sensed that — I’ve rewritten my job description a couple of times at Help Scout and I sensed that in order for me to continue in the role and continue to justify myself being in the role, it was important for me to write a new job description. So, this is actually Nick 4.0. I’m not sure if you can tell, but it is Nick 4.0, at least in the Help Scout context.

CLAIRE: [Laughs] Noted.

NICK: And so, there were a bunch of reasons why I just felt like I was a bit burned. I love the work. I got to the point where I was really looking forward to taking a little bit of time off. But I felt like it was going to be even better for the company in some way and I wasn’t quite sure how. One, I knew going in, like three or four months in advance. So, I was able to make a big list of things that felt like dependencies that I wanted to get off my plate before I left. So, that exercise in itself was extraordinarily productive in a number of ways. But then I took a month off and not only was it great personally, I got to — I’ve been married for 13 years — I got to really reconnect with my wife. Now, she really loves Sabbatical Nick way more than Working Nick.

CLAIRE: [Laughs]

NICK: And asks for him to come back on a regular basis.

CLAIRE: That’s awesome.

NICK: We had a great time. But also, the company was able to — over the course of a month, your company is going to make some really big decisions and solve some really complex problems if you’re doing it right. And it was really great to see the company and the people in the company just kind of step into those roles and make stuff happen, make some really great decisions along the way. And as I came back, it was so much easier to instead of kind of go right back into the old glue role that I had, it was so much easier to say, “OK, the company is able to function without me in all of these areas.” Maybe one area where, “OK, I want to improve that area. I don’t feel like the company was optimal in this one area maybe because I was gone.” So, I want to fix that hole. But otherwise, I just felt the freedom to sort of redefine my role and determine where I felt like I could add value and where the company needed me to add value in the next several years. It’s just such a great way to come back and look at the company from a 60,000-foot view. Now, it’s great to see my friend, Joel, and all the folks at Buffer just did a sabbatical program.


NICK: Hopefully, it’s catching on. It’s great.

CLAIRE: I know Basecamp…

NICK: Yeah, Basecamp was doing it before us.

CLAIRE: Right. The founders are on our board. I know that they have employees. I want to say it’s every three year anniversary that they have an employee they take a month off or something like that. For every three years you work, something like that. But I think the thing that I found interesting was you’re the CEO.

NICK: Yeah.

CLAIRE: It’s different. I’m not going to lie. It’s different.

NICK: I’m semi-ashamed to say, but aren’t all ideas originally Basecamp ideas? Most of them.


NICK: Jason and DHH do a great job with all things remote and culture. I’m pretty sure we probably did borrow that idea from them and it wasn’t the first.

CLAIRE: Oh, no, no, no. I guess what I’m astounded by is it’s not just anyone taking it. I actually don’t know if Jason — I actually should ask them. I don’t know if Jason and David had ever taken a sabbatical.

NICK: Yeah, it would be a good question.

CLAIRE: David, maybe. I don’t about Jason. I don’t know. Maybe? Maybe when he had his kid. I’m not sure. I just think that it’s different, I think. I’m not saying that employees are more replaceable or anything. I just mean that when you founded a company and you’re the CEO, like a month off?

NICK: Yeah.

CLAIRE: It’s unconventional.

NICK: The real measure of a good leader is what happens when you’re not around. Any manager, you’re not supposed to be in the weeds with people. You’re supposed to free up your people to do their best work. While it may be harder for somebody that’s an individual contributor, somebody that has their hands around the work all the time, for a manager, your job is to make yourself useless. If you’re super busy as a manager and you’re in the weeds as a manager, you’re probably not doing it right.

To some extent, you need to leave those challenges you have to fix. And so, I thought it was really important for me, not only to set an example. Because we started the sabbatical program — it was every five years. We’ve already moved it down to every four. I just felt like it was important for at least one of the founders to go ahead and take the time off, to reinforce the fact that, “Hey, we’re serious about this and you should totally take the time once you’ve been at Helps Scout for a while.”

CLAIRE: Absolutely. I think it’s something as CEOs and as founders and managers that we don’t realize. Whatever policy or idea that you suggest and you want other people to do doesn’t really mean anything unless you’re doing it yourself. It really does. It just never really gets the traction you want until you’re like, “OK, I will do it.”

NICK: Yeah, totally true.

CLAIRE: What an incredible example. Nick, thank you so much for your time. I literally could talk to you, we could just chat for hours. So, to respect your time, we won’t be doing that. But I do want to ask you one last question here. Circling back to the very first thing you talked about, around what you felt like you learned the most being a leader which is increasing self-awareness and putting ego aside. How does one do this, is my question. How do you try to actively or maybe just surprisingly find ways to increase your self-awareness?

NICK: These days I’m really lucky, I have a coach that I work with. I used to hang out with her twice a month. Now, it’s just once a month. But I’ve gotten to the point where I do know my demons really well and I know some of my character flaws really well. She’s a source of ongoing accountability with me. So, discovering those things, it’s shocking to me how many people aren’t interested in discovering their demons or character flaws, depending on how you want to refer to them. I refer to them as demons because I like to really…

But I’ve gotten to the point where I do know my demons really well and I know some of my character flaws really well. She’s a source of ongoing accountability with me. So, discovering those things, it’s shocking to me how many people aren’t interested in discovering their demons or character flaws, depending on how you want to refer to them. I refer to them as demons because I like to really…

CLAIRE: It personifies it a bit more.

NICK: Yeah. I like the negative connotation because understanding those means that you can have a better grasp of them.

CLAIRE: And by the way, I’m actually not shocked that people don’t want to know about them. I think it’s just because you have really good intentions. But I think for most people, the default is actually like, “Ahhh, it’s the last thing I want to think about.”

NICK: I think that it’s important for people to know that everyone has them, everyone that breathes air. The way I look at it is that everybody has a character that’s made up of several different traits. And those traits can have really positive sides to them and the same trait can also have a negative side to it. I look at ego as one of those where like it gives me the confidence to be an entrepreneur and still be able to sleep at night. But at the same time, it can take up all the oxygen in the room and prevent others from adding value if I’m not careful. I always just think of the negative side of a character trait as the demon side.

I’m a passionate guy. I love to talk in a certain way and I love to have an opinion but that also manifests itself as anger sometimes, and I have to be really careful about that. So, once you realize, “I don’t have demons because I’m a bad person,” it’s actually something that everyone has, and so, by way of discovering them, I can have better control of who I am and the person that I want to be.

I don’t know, that gives me a bit of comfort. It’s not that I’m messed up. It’s not that I have to feel bad about it. It’s just that understanding my character is a really key part of being the person that my wife wants me to be, my co-founders want me to be, the people that I work with want me to be. And it just feels like it’s my responsibility to understand that a little bit better.

CLAIRE: I think you do something really wonderful in your explanation of that which is one, you’re calling them demons, yes, because it kind of personifies it, makes it negative, like it gives you something to look at. But what I think that actually does is it removes the sense of, like you’re saying, sense of self-worth and identification with what that sort of ill aspect of yourself is. I think a lot of times, you don’t want to look at that reflection in the mirror because we go, “Oh, this means that I’m not a good entrepreneur. This means I’m a terrible human. This means I’m not worthy of love,” whatever those things are. And I remember I interviewed this wonderful entrepreneur whose name is Desiree Vargas Wrigley. She runs this great company called Pearachute and she talked about her biggest lesson that she learned was removing that sense of identity from the ups and downs in the business and from those personal characteristics. But I think what you’re talking about even more specifically is weakness and flaw and really just saying, “Well, that doesn’t make me a bad person. It just makes me a person.”

NICK: Totally. I don’t see how I would sleep at night if I really thought I was a bad person. [Chuckles]


NICK: It’s just important to know that — and by the way, if you know some of your negative character traits, then think about what’s on the opposite side of those. How can I leverage that for good in other people’s lives and in the world at large. Because every character trait, in my opinion, has a really positive aspect and a negative aspect. It all depends on how you use it.

CLAIRE: Absolutely. Completely agree. Nick, thank you so much for all the insights you shared, and for joining us today. So appreciate it.

NICK: My pleasure. Always good to hang out with you.

CLAIRE: Awesome.

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.