The Remote Show

Show Notes:

This week we're excited to share our conversation with Claire Lew, the CEO of Know Your Team. We learned an incredible amount from Claire about management, remote work, entrepreneurship and much more. Claire is one of the leading voices on how to improve your management skills and become happier at work. You're going to want to take some notes for this one! We certainly did.

Equally as interesting as the software itself, Claire's journey to where she is today is an inspiring one. From her early success to finding and developing a product that helps people, Claire has extensive experience yet remains incredibly humble. We think this is one of our better conversations, and we hope you do to.

Know Your Team
is a management software tool that offers best practices, guidance and a community of peers to help you become a more effective manager. It is particularly popular in remote teams, and we highly recommend that you check it out if you'd like to improve as a manager!

Visit: https://knowyourteam.com/ and sign up for a free trial!

Please check out Claire's blog, found here: https://knowyourteam.com/blog/

And follow her on Twitter: @clairejlew


[00:00:00] Matt H: Hello, everyone. My name is Matt Hollingsworth, and welcome to another episode of The Remote Show, where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community for remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire.

[00:00:24] My guest on today's show is Claire Lew. Claire is the CEO of Know Your Team, a profitable software company built to help people become better managers, leaders, and coworkers, and ultimately, run more successful companies. Claire is also a great writer, communicator, and leader in her own right and is focused on helping people become happier at work. I encourage everyone to read Claire's blog as it is one of the most valuable management resources available, especially for those of you managing remote teams. So, Claire, thanks so much for coming on the podcast. We really appreciate it.

[00:00:53] Claire Lew: Yeah. You bet, Matt. Happy to be here.

[00:00:56] Matt H: So, I like to start with people's background because I always think it's interesting where people got their start. So, can you go into a little bit about where you started and how you got involved with Know Your Team?

[00:01:07] Claire Lew: Yeah, sure thing. Yeah. I guess to really sort of clear the air for folks who might not know Know Your Teams, we're a piece of software that helps managers avoid becoming a bad boss, and the story really start with those last two words of "bad boss." So, I had a really bad boss about seven or eight years ago. It was the first real job that I had had working for someone else coming out of college. Prior to that, I had started my own company while I was still in school, and while I was graduating in the first year out, had started this company and then decided, "You know what?" I don't know if that's really what I want to do.

[00:01:44] The company had end up doing really, really well, got acquired and ... Yeah, did really well, but went to go ... Yeah ... work for someone else and was really young, like 22, 23, and actually really loved my coworkers and the work itself, but I hated my job because of my boss at the time. You may be listening to this, folks, on the other end or you, Matt, can relate, like, "Wow. It is crazy how much having a bad boss affects your life happiness."

[00:02:12] Matt H: Yeah.

[00:02:12] Claire Lew: It just sort of seeps into everything. The craziest thing was it was a really small company, only six people, and my boss, he was a really good person, really good intentions, he just, though, had no idea how bad he was. He had no idea that he was playing favorites, that he wasn't churning a good vision, that there was no sense of trust and transparency in the organization. Again, this is a tiny, tiny company, and I'm flabbergast, just like, "Oh, my gosh. How can you have so many blind spots as a leader?" Right?

[00:02:45] When I was in college, I'd actually studied learning an organizational change, so the study of how leaders think about problems and different frameworks of, really, the greatest organizational challenges that we face, and this is obviously one that was covered, but it was crazy to watch it unfold in real life. Then, like I was saying, just blew me away how much it impacted me on a personal level, and so I started doing all this research trying to figure out, "Well, what out there exists?" I was like, "Maybe I can use a piece of software or hire a consultant to come and help the company," and nothing existed that I thought would be helpful for helping this CEO become a better leader and get to know their company better.

[00:03:24] So, I decided to create a solution. I decided to quit my job and start a company. At the time, was like, "No idea what the company is going to be," truly, but wanted to really commit my life's work to solving this problem. Didn't really care how long it took. Like I said, had no clue what the form it would take, just set aside, like, 10 months worth of savings and was like, "All right. Here I go."

[00:03:45] Matt H: Wow. That's super interesting. Did you find that it came to you, the idea as it exists right now for Know Your Team ... Obviously, this is a process, I'm sure, that took quite a few iterations, but where did the idea start in terms of the Know Your Team concept?

[00:04:00] Claire Lew: Yeah. Well, so, the underlying thrust of Know Your Team is trying to answer the question, "How do I become a better leader?" Unfortunately, today, we don't feel like there's a very good answer. When you ask someone, "Yeah, I just got promoted. I'm a new manager. How do I learn how to become good at this?" people will say, "Here's some books. Maybe an executive coach," or, "Here's some mentors to talk to," or, "Watch some of these TED talks," or, "Maybe you can go on Coursera and take a few courses," but it sort of hit or miss or it's a lot of theory, but with books, you can't put it into practice, and with mentors, they're not always available. Then, some people are just like, "Oh. You just have to do it and then you're going to learn trial by fire," and so you do that and you're like, "Whoa. I'm making a lot of mistakes, quite expensive mistakes, painful mistakes. There has to be a better way."

[00:04:47] So, that question, honestly, I've been asking since 2012, 2010, when I was quitting my job to come up with solutions. So, it's always been at the core of what we've done. It's just come through a lot of iterations. So, yeah, when I decided to start my company, I actually, originally, started a consulting practice, working in-person with CEOs, working one-on-one with them to help them get to know their team and get to know their company better and uncover their blind spots, and my first client was actually a company called Basecamp, which you may be familiar with, obviously running-

[00:05:20] Matt H: Oh, wow.

[00:05:20] Claire Lew: ... We Work Remotely. Then, for folks who are listening, they used to be called 37signals. They make project management software of over 15 million customers, I want to say, and their CEO, Jason Freed at the time, said, "Claire, oh, my gosh. This is my biggest problem right now. I really feel, especially as a remote company, I really feel like I don't know my team as well as I would like." So, they were my first consulting client, and the project I did for them went extremely well. They learned a lot, made some changes. But I knew, ultimately, I didn't want to be a consultant for forever. I wanted to help more people and have it be an accessible solution. I don't always think consulting offers that.

[00:05:58] So, I was working on my own software product at the time, but coincidentally enough, Basecamp was also building their own software product at the time, and so this was ... Yeah ... maybe about five years ago. That product was actually Know Your Company. So, they had originally built this prototype to help themselves get feedback within the company. It ended up doing really well, so they started to sell the product. It really took off, but they wanted to really focus on Basecamp as their flagship product, so Jason approached me and said, "Claire, I have this crazy idea. We've never done this before, but what if we spun out ... " what was called Know Your Company at the time ... "What if we spun out Know Your Company to be its own separate company, not just separate product, like totally separate, you run the whole thing, we'll split equity 50/50, we'll just be on the board, and then you build the thing from the ground up? What do you think?" I was like, "Yes. That is my dream. That's what I've been trying to build."

[00:06:55] Matt H: Yeah.

[00:06:56] Claire Lew: Granted, they didn't give us any team members, Basecamp team members, designers, or engineers. I was going to build my own team. We didn't get any funding from then. We just, literally, got the product and the customers, which, obviously, is a nice leg up, but started at zero and (crosstalk) company and became profitable, though, in month one and have been profitable since. I've run the company since then for the past five years. Yeah, supporting over 15,000 people over the world using the product.

[00:07:24] Then, most recently, we changed the name of the company from Know Your Company, which was focused very much on CEOs and getting feedback ... Just in the past five months or four months ago, we relaunched the company as Know Your Team to be focused, exclusively, on helping managers and new managers on becoming better leaders. So, that's sort of the overview. We can dive in wherever you want, Matt, but that's the evolution of answer this question of, "How do you become a better leader?" and all its different forms.

[00:07:54] Matt H: Yeah. One of the things that would interest me to know about would be for somebody that comes to your product and are searching for an answer to the question of, "How do I become a better leader," do you find that those people are already in the mindset of wanting to learn and, therefore, are more approachable in that sense, and maybe the people that really need your product aren't the people that are going to be going and approaching you from the start? Do you have a way of having people referring, I guess, people to your product? For example, when you started, could you have referred your boss to your product and said, "Maybe you should ..." Honestly, you'd have to pick the language, but, "Hey, have you checked this out?" kind of thing?

[00:08:36] Claire Lew: Yeah.

[00:08:37] Matt H: Because I would be curious to know how that comes about and how you attract people to your product.

[00:08:42] Claire Lew: Yeah. I think that's a great question. It's a question I think a lot about because, to your point, the folks who really need our help the most are the leaders who don't know that they actually have the problem. That's when any problem is the most dangerous. It's when you have no idea that you even have one. So, unfortunately, we can't help people who haven't yet recognized the problem. To try to convince someone that they have a problem is not a sure path to improvement, right? The only way you can really improve is, as they always say, "Step one is you have to admit that there is any improvement to be made."

[00:09:14] So, the way to do that ... In a lot of ways, it's why I do so much writing. So, if you go to KnowYourTeam.com/Blog, you'll see that I write a ton about all the learnings that I'm finding, that our customers are finding, that folks I interview are finding, that the thousands of folks that we help with Know Your Team are finding around, "Oh, wow. I didn't know I was making this mistake," or, "This was a lot harder than I thought," or, "Wow. Doing this one thing that I thought was going to be good was actually bad," and with the intention that if a leader who doesn't yet know they have a problem will read it and be interested in learning more and then perhaps realize, "Oh, wow. I actually make those mistakes myself.

[00:09:53] So, that's the way that we try to draw awareness to that issue. It's a really tricky thing, though, because, to be completely honest with you, Matt, the only way you ever really know and are ready to take action on that problem is when it really burns you. So, the folks that we have coming to you as Know Your Team are people who have had a key hire leave, they've had employees tell them, "You're really screwing up," or, "You're ruining my life right now," or they realize that the team is underperforming and it's their fault because of how they're running things or not running things well as a manager, and so unfortunately, yes, you can read blog posts and take assessments and have mentors and executive coaches nudge you in the ribs, like, "Hey, maybe you should pay attention to this," but really, I think the folks who need that awareness the most only gain it when something really bad happens, which is human nature, right?

[00:10:58] Matt H: Certainly. I also think that the writing itself is ... One of the reasons I wanted to have you on the podcast was to discuss your writing. I'm a big fan, and that's one of the ways-

[00:11:07] Claire Lew: Oh, thank you.

[00:11:07] Matt H: ... I came across you, actually, by your blog posts and just the value that I think that creates for people. So, that's really fantastic. I also think, too, that for those of you out there who might have the problems that Know Your Team can help address when it comes to your boss, it might be a good way to approach the subject and say, "Hey, this is a super interesting article. You should take a look. I got a lot out of it," for example.

[00:11:33] Claire Lew: Yes. To your point, Matt, it's actually the reason why Know Your Team is effective is also a proxy, is to be like, "Oh, you know what? I've came across this tool." I was on a panel recently and someone came up to me afterwards and they're like, "I don't know how to let my leaders know that they have a problem and that they should be using something like Know Your Team," and that's what I suggested. I was like, "Use the blog posts as a scapegoat or use the tools as scapegoat and say, 'Hey, I happened to read this or find this, and it was interesting,'"

[00:12:00] Matt H: Yeah. I'd be curious to know a little bit, too, about ... Correct me if I'm wrong if this is relevant or not, but one of the things that I think about sometimes when I hear about people that might need the products that you offer is people that are maybe founders, maybe have started the company, and have grown to the point where they become managers of larger teams and then don't realize that they have those things missing from their toolbox. Do you find that most of the people that come to Know Your Team are founders themselves or is that a bit of a mix?

[00:12:30] Claire Lew: Yeah. Another good question. Total mix. So, for the first, I would say, three years of running what was previously called Know Your Company, we actually exclusively focused on helping CEOs and founders because the growing pains were so easily identifiable, like a doctor and the way they hear symptoms, and you're like, "Oh, yeah. No. That's the common cold," or, "That's an ear infection." There's very specific patterns that happen for founders and CEOs, and so in the beginning, it was very much them. As we started to write more and share more of our knowledge, we realized that our audience was actually much wider and that folks who were really feeling the pain were new managers. So, today, I would say that the majority of folks who come and use our tool are first-time managers, newly promoted managers, and of companies of all sizes. So, everything from 8-person startups to 800-person corporations.then, of course, as well, CEOs and founders of growing companies who find themselves in this situation of, "Ah, I wish I knew my team more."

[00:13:30] Matt H: Right. So, I wanted to take a step back a little bit to talk about your team and growing your team. Obviously, you're well within the goal posts of what Know Your Team is all about, so for you as a CEO, how much of your product has come out of just your own experience or is it mostly data taken across the board for people that are your clients?

[00:13:49] Claire Lew: Totally. So, I would say that the majority of our philosophy and methodology is based off the data and the insights that we collect over thousands of people that use our product, with the thousand plus people in our community, and the hundreds of folks who I talk to, whether it's through our podcast or conferences, et cetera. The reason for that is because I think the problem with most "thought leadership," around leadership and most of the content around leadership is that it's based on an individualized experience that's then projected as being the truth, and I think that the way to be successful as a leader is actually to understand the set of possible actions and results, to understand what a handful of people consider best practices, and not to just be isolated by your own personal proclivities or what you would like to be true. It's a huge problem.

[00:14:52] There's nothing wrong, obviously, with speaking from your own experience, especially when it's worked really well for you. I'm all about sharing what's personally true for you because it's likely personally true for at least one other person. My hope, though, or what I think is the greatest value that we can offer with Know Your Team is not to be dogmatic about, "This is how Claire feels about leadership. This is what's worked for her." Here's the thing, I carry my own personal experiences, inclinations, preferences, biases, and that's completely different, absolutely, from about every other single person on the planet, so how could I ever impose that what I personally have experienced is the only way to think about it?

[00:15:35] What I would prefer to do, and I think this is, hopefully, in service to most people is to go, "Here's what several people, minimum, have been saying," or, "Here's what thousands of people have been saying. Here are the nuances and differences," and then based off things that I've observed or read or researched, "Here's my take on how you can cut through the noise." So, if you're leading a team of this many people or if you happen to working with a person who's of this temperament, "These are a set of things that you could do." If we don't do that, we just will guide people poorly. Again, it's the reason why so much of the content currently out there around leadership is just so bad.

[00:16:14] Matt H: Yeah. I had a question about remote work specifically. So, something I hear quite often about remote work and especially people who are managing remote teams is that everybody's just trying to figure it out. Obviously, that comes with companies in general, but especially with remote teams because of the phenomenon of remote work and as these bigger companies decide to go remote or stay remote gets larger and the pool of companies that are doing that is bigger and bigger, managers often will tell me and people just generally will tell me, "There's no playbook. I have no reference point to know whether this is the right thing to do or not," and that's a struggle I hear quite often. Do you, at Know Your Team, focus on remote work and those specific problems that come up as a result of working in a distributed team or is that all part of what you're trying to do at Know Your Team?

[00:17:01] Claire Lew: Yeah, sure. So, it, no doubt, colors the work that we do in a sense. First and foremost, we are a remote team ourselves, the company that we originally spun out from was a remote team, and wrote a book on remote working, so there's, no doubt, influenced by that. I've noticed, though, in the research that we've done, anywhere between 40 to 60% of our customers are remote in some capacity, right?

[00:17:24] Matt H: Wow.

[00:17:25] Claire Lew: Yeah. What we've noticed in working with folks who use Know Your Team or folks in our online community, The Watercooler ... I'm actually writing right now a guide on managing remote teams. But what we've noticed is the reason why we have so many folks who want to use Know Your Team, who are remote, is that the difficulties and dysfunctions and obstacles that happen in running a team are only magnified when you are remote, and so it's not that there's necessarily a different playbook, it's just that you have to just be a lot better at running a team than you would have to be in person because you can't rely on a lot of the in-person crutches or reading someone's body language or getting to go out to lunch with them Monday through Friday. So, you have to compensate in different ways and pay extra attention in different things. It's not that it's a different playbook to run a remote company, it's that it's different points of emphasis and closer moments of paying attention, and that's true of ... I've interviewed dozens and dozens of remote leaders who've really echoed that.

[00:18:26] Matt H: Yeah, that makes total sense. I think, obviously, you are the expert here, but for us and for myself, I find it's easier to not be a good manager or it's easier to not be the good teammate as a remote team because you're not constantly seeing somebody on a regular basis, you're not forced to, necessarily, check-in or have that one-on-one or whatever, so you have to be very deliberate about what you do on a daily basis to make sure that you are achieving your goal and being a good teammate.

[00:18:52] Claire Lew: I think you're spot on, Matt. What we've noticed, and I wrote a big piece on this on our blog, actually, about the eight things that remote companies do differently. Essentially, what they do is they take the most crucial parts of building a successful team, you have to actually focus on them a lot more. So, for example, in running a team, communicating is, obviously, granted, important. People know leaders need to communicate. Typically, conventional wisdom is that you have to overcommunicate as a leader or repeat the same message. In a remote team, the remote leaders that we talked to said, "Oh, my gosh. That's even more true." If you think you need to repeat yourself in person, you need to repeat yourself in writing, you need to repeat yourself on Zoom calls, in Slack, in Basecamp, whatever it is. It is overcommunication almost to an extreme in a remote company. So, that was one element.

[00:19:38] Another piece was the importance of onboarding. Again, conventional wisdom in building a successful team that the way you incorporate new members on the team is important. Well, for remote teams, that's even more important. So, I remember talking with Wade Foster, who's the CEO of Zapier, and he's like, "Oh, yeah. We actually fly folks in and do something called Airbnb onboarding, where we have folks working together in the same location for the first few weeks because that onboarding process is so critical to us." He's not the only CEO who does this, but you can imagine in an in-person company that that emphasis might not be as strong.

[00:20:14] Another thing is around the empathy that comes in the workplace and hiring folks for empathy. So, one of the things that happens, and you might be able to relate to this, Matt, that happens in a remote setting is, because you can't see people's facial expressions or hear their tone of voice, when you receive a Slack message and it's very direct and to the point and it's like, "Do X," there's a lot of room for interpretation of like, "Oh. Is this person mad at me? Did I make a mistake?"

[00:20:40] There's a lot you can read into very easily, and so as a result, you, again, really clear the air, you overcommunicate, you assume best intentions, and you can really focus on ... you're forced to focus, rather, on being a lot more empathetic in working with your teammates because you can't always see them, so you just have to assume, "Okay. This person probably is just trying to communicate something, and so that's why they just wrote this one-liner really quickly in Slack," versus, in-person, that stuff bubbles, right? That empathy isn't something that you really attune to as closely because you'd be like, "Oh. I can just pull that person in the hallway and maybe we can talk it out," or, "I'm going to see them in a little bit. I don't want to bring it up," right? In a remote ... There's all these forcing functions of good team practices, and those are just a few examples.

[00:21:30] Matt H: Yeah. To your point there ... That's super interesting. I hadn't really thought about that before, but you can definitely tell, even when you're not talking to somebody in person in an office setting, you can just tell when something is off or when you may have rubbed somebody the wrong way. You can usually tell something's going on whereas in a remote team, if you're not on a call, if you're not seeing the person face-to-face, you might have no idea that you affected somebody in a way that you didn't intend to, and that might be good to know for people out there who are wondering, "Hey, am I alone in thinking this or feeling this?" and the answer to that is, "No, you're not."

[00:22:05] Claire Lew: Right. Everyone's struggling with it. What's interesting is ... So, that means that when you are hiring for a remote team, you pay attention to that, right? What is this person's emotional IQ or what is this person's desire to assume positive intent instead of assuming the worst in people? You actually actively seek folks out who scale really well in that dimension versus when you're in-person, and so as a result, you have a more empathetic team, higher empathy and higher emotional intelligence, obviously a lot less friction, versus, again, in an in-person company, maybe that's not something you're going to screen for as much because you feel like, "Oh. Well, we just talk it out kind of when it feels right," which isn't always the case.

[00:22:44] Matt H: It will come eventually on a daily basis in an office setting, but it won't necessarily come up on a daily basis if it's a remote team. Yeah. I think, just to overemphasis or emphasis future, that you're not alone out there for people who are wondering if somebody sent them a Slack message and stewing on that for the day. At least in my experience, I would say either clear the air right away or jump on a call and see them face-to-face, and so you can clarify that way because that's helped me at least in getting through that.

[00:23:13] Claire Lew: Totally. Here's the thing, if you want to be a successful remote leader, you know that that's something you have to correct for or compensate for immediately, and when you are a leader in a in-person company, you might not learn that lesson for months if not years. So, it's really interesting how being in a remote environment really focuses and emphasizes things that, to your point, Matt, you have to be more deliberate about. Trust is another big one of them. Again, conventional wisdom says, "Oh, yeah. You need to build trust in your team. You need to trust people to do the work." In a remote team, as a leader, you have to or else the work doesn't get done. You can't see people come into the office. Maybe you don't even know if they're online. You truly only have the results to go off of, and that forces a leader in a remote setting to really give and be generous with that trust, typically a lot more than if you're in-person.

[00:24:08] Matt H: Right. So, I wanted to touch on a little bit about what you were talking about there with the hiring process, and obviously, you can speak to Know Your Team, but also, generally speaking, for the clients that you work with, how do you measure for those emotional intelligence aspects that you mentioned that are so important? What do you look for specifically in somebody you're bringing on?

[00:24:28] Claire Lew: Yeah. So, I don't know if I believe in measuring emotional intelligence. I know whether it's Daniel Goleman's foundational work on this or ... There are a lot of assessments that you can truly Google on it, but I don't know if I really believe on resting my hat on that and saying, "Oh, that's how you really know if someone can send or receive the Slack message without getting overly emotional." So, what I really look for in hiring, and especially in trying to understand how empathetic is this person going to be is, first and foremost, the level of humility that they have in how they talk about themselves, things they've accomplished, honestly, almost every aspect of what I might ask them.

[00:25:18] The reason for that is when you are just committed to saying what the truth is instead of trying to fluff it up a bit or posture a bit, that shows an extreme amount of self-awareness in how you want to be seen and how you want the other person to feel on the other side. To me, the other thing that it communicates is that you put the team, first and foremost, their preferences, their goals before your own. Really, that's at the heart of what empathy really is and what emotional intelligence is. It's the ability to put yourself, yes, in someone else's shoes, but really, also, not just to put yourself in someone else's shoes, but actually to put their own interests even before your own and to consider their interests before your own. So, that's, first and foremost, what I look for.

[00:26:12] The other thing that I also tune an ear towards is if the person actually will answer the question that I ask in the sense that it obviously reflects how well someone listens, and the ability to listen, to really take something in is, again, a sign of the awareness and intelligence that this person has in thinking about others and wanting to really hear what's being shared instead of just thinking about putting forth their own point of view.

[00:26:40] But in terms of measuring it, Matt, I think humans are just a little bit too complex to put a number on that sort of thing. What I will say most broadly, though, that my goals are personally ... Again, this is all a person opinion around hiring and just the mentors that I've had who've taught me this is that, I think, the whole purpose of the interview process is to understand what truly motivates a person because, at the end of the day, that's your role as a leader, right? It's to create this environment where you can get the results that everybody, hopefully, wants and that you yourself want to happen, but the only way you can do that is to line every single person's motivation towards what you're trying to get towards.

[00:27:26] So, understanding what actually motivates a person is the single most important thing. And it's because you can't really change what motivates a person. That is for them to rightfully decide and stick true to. So, if you don't know what motivates people or you realize it's the wrong thing or doesn't fit and align with where you're trying to go, it's a huge, huge problem. So, for me, it's less about skills and less about traits than it is understanding what really motivates a person. That's how I think of the hiring process.

[00:28:03] Matt H: That's interesting. That's why I love that question because I get so many different answers to, "What is your hiring process?" This, again, lends itself to the point that everybody has different ways of doing things and maybe there's not one way, one answer for every company. Obviously, there isn't.

[00:28:20] Claire Lew: Gosh, no. Yeah. The other thing, too, I'll add that ... This is what a mentor of mine taught me. Something that I'll do is I'll ask really consistently about what people have done, ask about their past, ask about when is a time when ... Et cetera. This is broadly done, but the reason why I do it isn't so much to listen to the exact examples, et cetera, but it's two things. One is to identify consistency and patterns and also to figure out is this person BS-ing you. The only thing that you know actually to be true is what people have done, and so to understand in every choice ... And I'm not speaking even specifically about, "Oh. It means they need to have 12X years of experience." It's not that. It's understanding consistencies and patterns and actually decisions and thought processes and examining that past channel instead of just asking, hypothetically, how might someone decide or how might someone be or how might they act. Again, if it comes down to motivation, that's all revealed in past decisions and thoughts and actions.

[00:29:28] Matt H: Right. So, you kind of already answered my next question in that last one, which I think is fantastic, of how people are motivated or what motivates them. Do you find that a lot of your job as a CEO is, in fact, motivating people or is it kind of that they've already come on and been motivated just by working in your company? How much of your job is spent trying to find a way to motivate people to do great work or to extend the mission of the company?

[00:29:52] Claire Lew: I'm so glad you asked this question, Matt, because it is my biggest ... I don't know if it's pet peeve, but thing that irks me, which is ... I actually strongly believe that leaders do not motivate. They do not motivate people because people are already motivated. People already inherently have motivation, so motivation is not a thing that leaders do nor is it a thing that leaders give because people already have it. Rather what leaders do is they create an environment for people's own motivations to be pursued in their own ways. People might say, "Oh, that's such a semantic difference, Claire." No, but it's a truly big difference because if you are focused on doing motivation or giving motivation or trying to motivate others, it's a mechanism for control, it's a mechanism for trying to get something out of someone.

[00:30:50] Matt H: Right.

[00:30:50] Claire Lew: When you really think about it, what you want is results, right? There's so many studies that have been done on ... Edward Deci's the seminal thinker on and researcher on this topic. He researched human motivation for 20 plus years. In all the studies that he did and so many of his comrades who studied the field of human motivation have found is that people don't perform as well if they have any inkling of control around them, whether it's controlling language, controlling habits, or any slight form of manipulation and control is completely counterproductive towards someone's learning ability and to the actual quality of the results. Things take longer, they're not as good, people don't enjoy the process as much. It's just all bad the minute you have control.

[00:31:40] So, the idea of, again, giving motivation, trying to motivate others, it is a form of control. So, the reframe it as this creating environment, what that means is it forces you as a leader to think, "Well, how do I, one, understand first what motivates a person because I'm not giving them motivation? They have it. I have to understand what it is. Second thing is then I have to understand how does that fit towards where the team needs to go? Is there alignment? Can I create alignment?"

[00:32:15] Then, once you figure out what that path is, you say, third, "Okay. Well, how do I create an environment for that motivation to go in this direction and help us move forward to where we want to be in the best way possible? Does that mean I need to help this person work under certain ... They work best in the mornings, so I need to leave them alone in the mornings," or, "Does this person need extremely high-detailed context in order to execute a project well," or, "Is this person really motivated by creative projects? Okay. I need to be giving them more autonomy," or, "I need to have them in a more creative role," right? So, now, you're not thinking, "Oh. I need to have a pep talk with this person," or, "I need to promise them a promotion or give them a reward." No, you're actually thinking a lot deeper about, again, focus on creating this environment instead of trying to impose a sense of motivation onto people who already inherently have motivation.

[00:33:05] Matt H: Yeah. So, everybody, I'm sure, is motivated by something. I'm so happy that, again, I asked that question because it's such a different way of looking at it, at least from what I've found, and it makes so much sense because if you're trying to motivate somebody ... Now that I look back on myself, the way that I was motivated wasn't about people forcing that on me because that wouldn't last. If you have to motivate somebody to do something, it's not going to last very long.

[00:33:29] Claire Lew: It's already failed.

[00:33:29] Matt H: Yeah. Yeah. You might get a little bit of a spike because it's going to be like, "Oh, I got to do this now because my boss just said that," but it's not going to last very long because that motivation wasn't there in the first place. That's super interesting. What would you say, then, is the most important aspect of your job as a CEO, and as a caveat to that, what do you think most CEOs miss when it comes to leading a team?

[00:33:51] Claire Lew: Yeah. Oh, boy. Yeah. How many hours-

[00:33:55] Matt H: Hard question.

[00:33:55] Claire Lew: ... we got here, Matt? Yeah. No. I say that tongue in cheek just in the sense of ... We've gathered so much research and insight into what successful leaders are doing. Most broadly, there are three categories that we've found that leaders who are successful tend to focus on. So, the first is they build trust in a team, and trust doesn't necessarily mean people liking you because people can like you and still not trust you. Trust is actually about intention matching your behavior. That's when someone actually trusts you. It's when you say very clearly why you're doing something and what you promise to do and then you actually follow through on it.

[00:34:35] So, leaders who are very effective at admitting their mistakes, communicating what needs to happen, and then actually following through on that are the ones that tend to be the most successful. It's interesting because we spend a lot of money and time as leaders in thinking about trust on things like all-company retreats and team-building activities and making information transparent. Not to say that those things aren't helpful in a company, they absolutely are, but in terms of if they actually contribute to building trust, not really. We ran the survey with over 1,000 people around trust and they said, "Yeah. The top three most effective ways to build trust is, one, admit your weaknesses as a leader and what you're struggling with, two, say why you're doing something, and then three is to follow through on what you do." So, again, it's intention matching behavior, and that's really what trust is about. So, that's the first biggest thing that we've noticed that leaders who are successful tend to focus on.

[00:35:29] The second thing is creating context. So, are you able to really, clearly ... This comes back to creating environment for people to do their best work. Are you able to create an environment where people actually know, one, what's going on and, two, where they're headed? Back to motivation, actually. This is really interesting. This is related to context. Harvard Business Review published a study ... I believe it was done back in 2010 ... where they found that the number one thing that they were motivated by, what employees said, number one thing, they said was making meaningful progress every day at work.

[00:36:08] Matt H: Wow.

[00:36:09] Claire Lew: So, if you as a leader can share context and say, "Here's how we're making progress, here's where we're going, and how far we're gone and how far we need to go, what's in our way, here's the map," so to speak, if you can provide that cartography of the landscape as much as possible, whether that's weekly meetings, write-ups, sharing key metrics, whether it's talking about the vision constantly, asking questions like, "Have I given you enough information about X?" or, "Is it clear who the stakeholders on this project?" Right? So, the more context that you can give as a leader, the better. The folks that don't really, really suffer and struggle when they're managing a team. So, that's the second thing, context.

[00:36:51] Then, the third thing that leaders who tend to be the most success focus on is honesty. So, being able to communicate in an honest way. The reason this is so key is ... This is how the work gets done, right? So, if you cannot give and receive honest feedback, then you can't make that progress, right? There's no way you can even start to build trust if you're not able to communicate honestly. Actually, it's interesting. In our tool, Know Your Team, we focus exclusively on these three buckets and have guides and tools all corresponding to each, but honesty is a tricky one because it's not just about you as a CEO being honest all the time and you delivering on giving good feedback and getting honest feedback, although that's important, it's about, also, creating an environment where people are going to feel comfortable, safe, psychological safety. There's been a ton of research that's been done and promoted around that, but it's how do you actually create an environment for people to feel comfortable being honest. That's the real hard part. We have a ton of resources in our tool to help do this, but it's those three things that leaders who tend to me most successful focus on. So, trust, context, and honesty.

[00:38:11] Now, to the second part of your question of, "Okay. Well, what do leaders tend to overlook?" there's a lot. I would say the biggest, the big six, and I'll run through them really quickly, I would say the big six, in no particular order, first I would say is their conception around trust. A lot of leaders think that trust is likeability, trust is charisma, it's team-building, right? But in fact, it's not. It's about your intention matching your behavior. It's about you being vulnerable. It's about you saying why you're doing something and following through. So, that's the first thing.

[00:38:43] The second, I would say, is actually around one-on-one meetings. We ran a survey with over 3,000 folks who shared their best practices around one-on-one meetings, and we found that most managers do run one-on-one meetings, and fascinatingly, I believe almost 90% of managers said that one-on-one meetings positively effected team performance. This isn't true just from the survey, but tons of CEOs and managers that I've talked to have said, "Oh. One-on-one meetings are so high-leverage, and yet employees, they do think that they're helpful, but not to the same degree." So, in the same survey, I believe it was, like, 70% of employees said that one-on-one meetings had a positive impact on team performance. So, an almost 20% difference in perceived effectiveness of the same meeting, which is fine, right? Yeah. But it's a pretty big gap. So, as a manager ... You think about how much time these meetings take, whether you're remote or in-person, how can we be improving them?

[00:39:38] So, the second biggest thing that leaders often overlook is preparing for these meetings well, asking good questions, and making sure that they're not using these meetings as a status report. It's such a waste of valuable time to really uncover important insights. So, one-on-one meetings, I would say, is the second thing that a lot of CEOs and managers overlook and not really utilizing them to their highest potential.

[00:40:03] The third, I would say, is how CEOs and managers spend their time. So, it's so interesting. A lot of managers, they think it's very easy to feel like when you're really busy that that means things are good, like, "Oh, yeah. I'm knocking things out," when, in fact ... I remember interviewing Michael Lopp, who's the VP of Engineering at Slack, and he told me, "Claire, being busy is a sign that you're messing up as a manager. The best managers choose not to be busy," and it's because when you're too busy, you don't have the space and the time to pick up on sensitive team issues, you don't have the time to focus on giving context, you don't have the time to build trust in the team. You're too busy putting out fires, adjusting code, in the weeds of the work too much. So, this misconception around how you should be spending your time is the third biggest thing.

[00:40:55] Fourth is vision. A lot of managers and CEOs don't focus enough on, again, providing that context, but vision in particular. Vision is a ... Oh, man, Matt. It's such a fluffy word. My goodness. It's up there with innovation and culture in terms of completely just cliched words in ... Yeah ... in our lexicon. Vision is purely a picture of a better place, so it's where you want to go, it's the destination, and so sharing what that is often isn't articulated enough, and it's powerful. It's not just, "Oh, here are our values," or, "Here's our mission statement." It's, "Here how the world will be better because we exist." So, that's something that's highly overlooked.

[00:41:40] Fifth is ... Managers and CEOs, we tend to be really nice, most of us, or we like being nice. I remember interviewing Hiten Shah, who founded Kissmetrics and is a wonderful entrepreneur who talked about how the biggest thing he wished he would've learned when he was a leader was around being nice. He was like, "When I optimize for being nice, it meant that I sacrificed actually doing things in the best interest of my team. I was paying attention to my ego of what's going to make me feel good and look good to my team instead of what decisions are actually going to be most helpful." So, when you're too nice, you postpone firing, you don't tell people when you think something's actually bad until it's too late. It's a lot of unintentional consequences that happen ... Yeah ... when you focus purely on being nice.

[00:42:34] Then, the last one, probably the most important, likely, is we have a tendency as leaders to, when we are approached with a problem, to solve it ourselves. Someone comes to us and they're like, "Ah, I need help with this," and you go, "Of course. Let me help. I'm going to get in there. I'll fix it. So, I'm going to pick up the phone, call the client myself or I'll get into Photoshop. I'll fix the design, whatever it is." Actually, someone who I mentioned already earlier in the show ... Yeah. I remember interviewing on our podcast Wade Foster, CEO of Zapier, and he was like, "If you are solving the problems yourself, it's actually a sign you've hired the wrong person because, in fact, as a manager, your goal is not to solve the problems yourself, it's to actually help other people solve the problems themselves. When you as a manager or the CEO are the one solving the problem all the time, your team, all of a sudden, they become reliant on you. All of a sudden, they start sending you all their problems."

[00:43:26] Now, two things happen. One, your team never learns how to solve the problem themselves because they know they have the quick out, and then, two, you actually become the bottleneck in the company. You slow everything down because you're like, "Oh. Whoa." Now, anything that's that level of difficult gets rerouted towards you and now it starts to pile up and things start to slow down, and there's so many CEOs and leaders who I've talked to where this is the case. So, making sure that you're not acting on that reflex just to jump in, clean everything up, but instead, to ask questions, to ...

[00:43:58] It's a more Socratic approach, saying things like, "Well, what have you considered?" or, "What would happen if we didn't do anything?" or, "How would you define success?" or, "What is making this decision tricky for you?" What you'll find is that most people, when they come to you with a problem as a manager, most of your employees actually already have an answer, they actually already know what to do, but they're scared of messing up or they don't have the confidence perhaps quite yet. So, really, what you're doing as a manager is you're helping your team learn to think for themselves more than anything. You're not solving the problem yourself. You're helping them learn to think for themselves.

[00:44:35] Matt H: That's great. I'm sure there are people out there scrambling with a pen and a piece of paper trying to get those down. Luckily, for them, we'll link to everything in the show notes as well. My next question is actually one that the listener might recognize. I've stolen it from your show. So, to turn the tables to you, what's the thing about leadership that you wish you had learned earlier?

[00:44:53] Claire Lew: You know what's so funny about this, Matt, is I have asked this question to tens and tens of leaders and I have such a hard time answering this myself because there's a lot. Oh, my gosh. There is so much I wish I would've learned. I think the biggest thing that I wish I would've learned ... Okay. There's two. Sorry. Just because there's so many, right? I'm just like, "Okay. I'm going to just pick one." No, I'm going to pick two.

[00:45:17] The first one is ... It's actually probably the best advice that I've ever gotten, which is to trust yourself, and I'm sure that's printed on, no doubt, thousands of motivational posters across the world that you can order off Amazon, but the truth of that statement I have learned the hard way. I remember the first company that I started, before I started it, I wasn't sure, "Oh, should I start a company or should I go ..." I had offers to work at multiple different types of companies coming out of college, and all the advice that I got, it was so interesting. My parents, who both went to get their master's degree and PhD, told me, "Claire, you should go to graduate school," and I was like, "Interesting. That's what they did, so that's the advice they're giving me. Very interesting."

[00:46:04] Matt H: Right.

[00:46:04] Claire Lew: Then, I would ask my professors, "Oh, what do you think I should do?" and then would say, "Oh, Claire, you should go work for a big company, and I thought, "That's so interesting. That's what they did," right? Then, I would talk to entrepreneurs, friends of mine who were founders, and I'd say, "Oh, what do you think I should do?" and they go, "Oh, you should totally start a company," and I'm like, "Oh ..." Everyone is biased by their own perspective, and whatever magic answer that you are seeking that somehow saves you does not exist. It is all within yourself. No one has lived your exact life. No one is you, and it's so obvious, right? But I learned that lesson, I think, and continued to learn that lesson so many times on.

[00:46:41] Even most recently when we made this big change going from Know Your Company focused on helping CEOs get feedback to now today Know Your Team, helping managers become better, making that decision, it's like, "I can't Google that somewhere." I can ask, also, as many of my mentors and friends and talk to my business partners as much as I want, but at the end of the day, I really have to trust myself with the decision. By the way, it's not a note of encouragement for just blindly listening to your own craziness and it's not, also, a blank permission slip to just go off gut alone, but what it means is to abandon that desperate grasping we have to believe that there is a right answer to anything in life. There is no cheat code, there is no answer sheet in the back of the book. It doesn't exist. You have to find the answer for yourself. So, that's the first biggest thing I think I learned.

[00:47:43] The second is ... It's to remember ... then, speaking very personally here, just for myself, is that I perform the best not in the high moments of tension or stress or rapid movement, but truly, when I'm most relaxed and at peace and this nice spot of confidence and control, but also feeling loose. It's interesting. Whether you are an athlete and ... I played tennis in high school and I remember the same thing. It's know that you run the fastest, not when you're all tight and you've been training really hard, like every single day and the before, it's like, no, when you've rested and relaxed and you're loose. That's true for athletes as much as it is for musicians, you don't play well in a piano recital if your fingers are really tense and tight, et cetera, and as much as it is for writing. I'm not a great writer when I mentally am just really tense and tight and I'm forcing it. You have to be really loose.

[00:48:52] So, as a leader, as a CEO, I found the same to be true. So, that means giving space to step away, that means saying, "No," to commitments that distract you from being in that relaxed state. It means having the self-awareness to know when you're not feeling loose, so to speak, and what it also means is getting in that loose, relaxed, confident, yet calm mindset also extremely when you are in moments of stress and tension. So, that's a huge thing I've learned is, when you're running a company, there's all sorts of interesting shit that gets thrown your way.

[00:49:36] It's like, "Oh, someone wants to leave the company," or, "Oh ..." your biggest client is leaving or, "Oh, this new competitor came out, hard decisions of, "Oh, should we partner with this ..." There's a lot of big decisions or moments of tension and stress and conflict, and I've had to learn that, "Okay, I actually perform the best in these moments, not when I'm brow furrowed, feel like I have to spit out an answer right at that moment, but when I'm loose relaxed." Again, I think back to, okay, tennis, piano, painting, writing, whatever it is, it's like, that's when I'm performing the best personally, and so just to remember that as a leader. Stay loose.

[00:50:13] Matt H: Yeah. That also comes from, I'm sure, lots of self-reflection, knowing yourself well enough to know what that looks like and what that feels like, and how to get yourself to that point. It's definitely, I think, an ongoing project for everybody is to try to find the frame of mind where you're most effective and the best that you can be. It's definitely an ongoing project for myself as well. So, Claire, I really appreciate how much time you've been able to give us today. I have a couple of more questions for you just in closing. The first is to do specifically, obviously, with the podcast being more remote-specific than anything else. What is your favorite tool for working remotely and without the option of Know Your Team and, also, I'm going to throw in the without the option of Slack?

[00:50:53] Claire Lew: Oh, really? That's interesting. We actually don't use Slack. Yeah. So, we run our entire business naturally, actually, on Basecamp, like everything. Basecamp has a feature called Campfire and that replaces our Slack. They have this great pings feature. But I almost feel like I shouldn't even count them, too, because their founders are on our board and we spun out from them. So, actually, my favorite tool for remote team is actually 1Password, who are clients of ours, long-time clients. I actually can't imagine ... Oh, my gosh. The volume of information we keep in there and the amount of security, and they do it really, really well. Has made our life easier, so big fan of them.

[00:51:29] Matt H: Yeah. We are, too. Same thing. So, one of those products where you just can't imagine your day going by without the ease of using 1Password, or at least I can't.

[00:51:38] Claire Lew: Yes, with you.

[00:51:39] Matt H: So, my next question is what is your favorite unplugged activity? So, what do you do outside of work and your team that you do to unwind and what do you enjoy the most?

[00:51:48] Claire Lew: Yeah, I have several. So, yoga is like therapy to me. So, getting out and just getting a good stretch in. Love yoga actually for the emotional benefits, too, strangely enough for anyone else who does a lot of yoga. It's as much as it is exercise and for my health reason as it is to feel centered. Then, I do a ton of painting when I can to, I guess, kind of flex the creative muscles that I feel like I don't always get to when I'm running Know Your Team. I feel like when you're literally in front of a computer just moving two fingers the entire day ... I do a lot of talks, I do a lot of writing, I do a lot of thinking about the product, a lot of reading and researching, interviewing, and there's this other part of me around making something with my hands that gets very, very itchy, and painting's the way I scratch that itch.

[00:52:43] Matt H: Nice. That's something that a lot of people feel the same way in the creative process of definitely being able to shut off everything else. It's not on a computer and it doesn't allow you to be distracted in a different way, so that makes a lot of sense. I wish I could paint myself, but not there.

[00:52:57] Claire Lew: Hey, you can, right? You can. It probably isn't very good maybe in the beginning. Trust me. I don't even know how good I would call myself now, but ... It's also a humbling reminder when I do any kind of art. I always try to pick up something new. I did ceramics a few months ago and done everything from print-making to knitting, you name it. But it's this nice reminder to suck at something, also, in the beginning.

[00:53:21] Matt H: Yeah. Yeah, definitely humbling. I have the same thing. I play the guitar, and I'm not at all, by any means, an expert at all, and it is nice when I started to learn how to play a song or whatever and realizing, "Hey, I have no idea what I'm doing," and, "This is hard."

[00:53:36] Claire Lew: I think it's a breadth of fresh air.

[00:53:39] Matt H: Yeah, totally. So, my last question here before I let you go is what is the best advice you've ever been given, and this can be in work or just in life, and you can go any direction you want to.

[00:53:52] Claire Lew: Yeah. So, Jason Fried, the CEO of Basecamp, he gave me a wonderful piece of advice I remember. About four years ago, we'd made a really, really big mistake in our code base with Know Your Team at the time. It was so bad. Oh, my gosh. I cringe thinking about it. What had happened is we'd had a bug in the system that revealed private answers that were only supposed to be seen to the CEO and they were revealed to about 80 companies for some reason. Yeah.

[00:54:19] Matt H: Wow.

[00:54:19] Claire Lew: The worst part about it is we had no idea about it because no one reported the bug for six months. So, it just was there. It wasn't until a really kind customer was like, "Hey. So, I don't think everyone's supposed to see these." I was like, "Oh, my God." So, I remember being faced with this situation, and we obviously fixed the bug immediately, but then the question becomes, "Well, what do you do?" Do you reach out to all 80 customers that it affected and let them know that this happened? If they didn't notice it already, why would you need to tell them that the mistake happened, right? Are you going to get some angry customers here? What should you do?

[00:55:01] So, I remember debating it back and forth with my team because there was some differing opinions, and so I remember calling up Jason to ask his advice on the situation, and when he says, Matt, is ... This is all he needed to say for me to make the decision, which is he said, "Claire, I love moments like this because they show what kind of company you want to be," and that just really hit home for me. It was just like, "Oh. Well, what kind of company do we want to be?" Well, we want to be one that acts with honesty and integrity and admits mistakes, even if someone doesn't point it out.

[00:55:38] So, I hung up the call with Jason and knowing what kind of company we wanted to be, personally emailed every single one of the 80 CEOs, told them exactly what happened, gave them a small credit as kind of a token of apologizing saying, "We're so sorry. Thank you for putting your trust in us. This will never happen again. Here's my personal cell phone," and sent the email and then brace myself for the angry reactions. What was interesting is I got a ton of email responses, but, Matt, none of them were negative, truly.

[00:56:13] Matt H: Wow.

[00:56:14] Claire Lew: Every single one said, "Thank you, Claire. Mistakes happen," or, "We appreciate the heads up," or ... We had a client in the Netherlands who said, "We have a saying in Dutch. It's 'Mistakes are made while doing work.'" He said, "You were just doing work. Mistakes happen." So, yeah, I've taken that piece of advice of, "What kind of company do you want to be?" with me to heart as well.

[00:56:35] Matt H: Right. That's probably one of my favorite answers I think I've got. This speaks to your point of before where you were saying that the CEO is there to reveal what your employee or your colleague already seems to know. It sounds like that was almost the case, is that you sort of already knew the answer already. It was maybe Jason's role to let you reveal that to yourself.

[00:56:52] Claire Lew: Yep. Exactly. He helped me think for myself. Exactly.

[00:56:54] Matt H: That's great. Well, Claire, I can't say "Thank you," enough for coming on the show. You've been so generous with your time. I think everybody should get a lot out of this, and we'll maybe make time for a part two because I have so many other questions I want to ask you, but I want to be aware of your time. Is there anywhere that you want to be sending our listeners so that they can read more about you or see what Know Your Team's up to?

[00:57:16] Claire Lew: Yeah, sure. So, yeah, if you found any of the resources or statistics, studies, insights that I shared interesting, definitely check out our blog. I write pretty regularly there, sharing all the things I'm learning and best practices around leadership, and that's at KnowYourTeam.com/Blog. Obviously, would also love for folks to try the product themselves and really put those concepts that I mentioned of trust, context, and honesty into practice. You can sign up, check out the product at KnowYourTeam.com. Then, if you were curious just for following what insights I'm learning on a day-to-day basis, I try to tweet as regularly as possible, too, and so my Twitter handle is clairejlew. Yeah, would love to see you over there, too.

[00:57:57] Matt H: That's great. Again, I can attest to both of those things. I follow you on Twitter and I read your blog regularly, even before I was planning on having you come on the podcast.

[00:58:04] Claire Lew: Oh, amazing. Thank you. So appreciate that.

[00:58:07] Matt H: That's great. So, thanks again, Claire. Hopefully, we'll have a part two coming soon.

[00:58:11] Claire Lew: Sounds great, Matt. Thanks so much again.

[00:58:13] Matt H: All right. Bye now.

[00:58:15] Thanks so much, again, for listening to the show. Be sure to check out WeWorkRemotely.com for the latest remote jobs, and if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone that we should talk to, advice you have, please feel free to reach out to us at [email protected]. That's [email protected]. If you'd like to sponsor the show, please go to WeWorkRemotely.com/Advertise for all of our available opportunities. Thanks so much for listening and we'll talk to you next time.

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