Remote Work Interviews

Conversations with leaders and innovators about how industries and organizations think about the future of remote work.
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Katie Burke: Chief People Officer at HubSpot
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Claire Lew: CEO of Know Your Team
February 20, 2019
Interview by Sophia Bernazzani
Photography by Justin Barbin & Northwestern University
Claire Lew is the CEO of Know Your Team, a software that helps managers become better leaders and avoid becoming bad bosses.

Claire Lew is the CEO of Know Your Team, a software that helps managers become better leaders and avoid becoming bad bosses. Previously, she founded two other companies, taught at Northwestern University, and served on nonprofit boards in Chicago, IL. In this interview, Claire talks to us about how she changed the company's entire product and strategy, what she's learned from partnering closely with Basecamp, and her advice for remote leaders, now and in the future.

Owl Labs (OL): Tell us a little bit about your team and about the transition your company, Know Your Team, made recently.

Claire Lew (CL): I'm the CEO of Know Your Team, and we used to be called Know Your Company. Today, as Know Your Team, we make software that helps managers become better leaders. We provide educational guides, software tools to save you time as a leader, and an online community of other managers to learn from.

The whole idea is, if you're a new manager or a seasoned manager who's feeling stuck, how do you actually learn how to get better? You can read books, but books can be one-sided and difficult to apply to your unique situation. You could hire an executive coach or attend a conference or join a CEO group, but those can all be expensive. I've been studying leadership and working with leaders over the past 10 years, but this was still a question I felt was unanswered.

That's what our company and our product are all about. About four years ago when we first started out, we were purely focused on helping business owners running small companies between 25-75 people. We primarily helped them with getting honest feedback, which is very crucial for any leader.

But what we've realized over the course of the past two years is that our audience had changed. Our audience were people who were reading our blog, and we saw our organic traffic to our site increase by 20x in only six months. So we started doing some digging into our blog audience and realized that they weren't actually business owners, but they're managers and they're people who love to learn about leadership. Additionally, we had launched an online leadership community that was quickly growing in members to more than 1,000 people.

We found that our biggest audience were people who were really interested in the topic of leadership, and learning how to become better leaders. We had a big audience of managers, but our product was for business owners, so we decided to actually build something to help the people that were telling us what they wanted. We launched Know Your Team for managers in December of this past year, and we changed everything. We changed the company name, the product, the pricing model, the website, everything.

OL: What was that decision-making process like for you, and what was required for you to actually make that change?

CL: First and foremost, the data was so clear in terms of the difference between our audience growth and our community growth. That, and the fact that our product sales were staying flat at the time with our product's first iteration. They were fine, but when you're growing your brand and the attention and the number of visits coming to your site is growing, but sales aren't growing proportionally, that really makes you reflect and ask some tough questions.

We also realized that the problem of manager training was one that no one had really nailed yet. If I asked you, "What's the software accountants use?" You think of Xero or QuickBooks. You ask, "What do HR managers use?" You think of Workday or Gusto. "What do project managers use?" Basecamp, Asana, or Trello. Well, there wasn't a clear answer to the question, "What do managers use?"

There's was no clear answer to the question of what software managers use, so we decided we should build that. There were a lot of ways to get there, and we took possibly the most radical approach. We took Know Your Company, changed the software while people were still using it, and tested different features. Then, we changed the entire product and company.

It was kind of a controversial strategy, and it made me realize that, as a founder and as a person who is in the business, the things you understand better than anyone else are the real levers you have to pay attention to that other people aren't paying as close attention to.

Data and passion for the problem we wanted to solve drove the change, and it was worth it.

If I asked you, "What's the software accountants use?" You think of Xero or QuickBooks. You ask, "What do HR managers use?" You think of Workday or Gusto. "What do project managers use?" Basecamp, Asana, or Trello. Well, there wasn't a clear answer to the question, "What do managers use?" There's was no clear answer to the question of what software managers use, so we decided we should build that.

OL: Can you tell us a little bit about your relationship with Basecamp?

CL: We definitely have a unique origin story when it comes to the startup world. We were originally a prototype of a software product for the company Basecamp, built and for folks who don't know about Basecamp. Basecamp is the world's most popular product management software, and they have almost 15 million customers after being around for 20 years. And the Basecamp team originally built our first tool, Know Your Company, for their own use. In 2014, Basecamp decided that, as a prototype and as a product, they didn't know much about what to do with it. It was working well, but they realized it should be its own business, so they spun it off and asked me to run it as the CEO.

OL: Do you have any insight into Basecamp from your experience with them as a company? They've really paved the way for remote work and structuring teams differently in tech.

CL: The co-founders of Basecamp sit on our board, and they're part-minority owners in the company. As a remote leader myself, I have the luxury of being able to ask for their advice on running the company, but I also get to watch and observe in real-time how they run their company. The thing that struck me when I first was exposed to how they run Basecamp was how rigorous they are about writing everything down. It's writing first and talking second.

What I've learned from the Basecamp leadership team that's been reaffirmed by so many other CEOs that I've talked to is that the best remote companies understand that you have to be a good writer as a leader in order to run your remote company well. Writing is a superpower for leaders of a remote company in particular. It's what is going to help you to be successful for those times when you can pick up the phone or tap someone on the shoulder to communicate something to them. Having to write everything down makes you more deliberate, more focused, and more clear in how you're communicating your ideas. I've learned so much from Basecamp, but the importance of writing is probably the biggest thing.

OL: How has working so closely with Basecamp impacted the way that you think about and have grown your team?

CL: We're a 100% remote team as well, so that's a big way Basecamp has influenced us. We're also a writing-first team. That's a best practice that I've taken and inherited from Basecamp. If I have a new idea and want to pitch something to the team, I write it up first. If I disagree with an approach that we're taking, instead of calling someone up or you or pinging them on Slack, I write up my thoughts first. The result is a more methodical and rigorous thought process, and I think we achieve better results because of it.

The second biggest way that I think Jason Fried and David Heinemeier Hansson, the founders of Basecamp, have influenced me as a leader is the importance of talking the talk and then walking the walk. Their advice has encouraged me to take action in a way as a leader that I'm very proud of. About 3.5 years ago, we made a huge mistake  probably the biggest mistake we've ever made to date. Our software had a bug that revealed a bunch of private information about 80 different companies. We didn't know about it until months later because one of our customers pointed it out to us, and we quickly realized what a big deal it was.

We were faced with a dilemma as a company: If no one else noticed the mistake, do we need to say anything about it? It was a huge mistake, so I decided to talk to Jason about it. I called him up at the time, and after telling him about the situation, he said, "Claire, I love moments like this. Moments like this help you decide what kind of company you want to be." And that's all I needed to hear.

I took that grain of advice and ended up writing a personal note to all 80 companies, explaining exactly what went wrong, why it happened, and saying we were sorry. I offered free credits to use Know Your Company and my personal cell phone number if they had any questions, and I braced myself for the reaction. I ended up getting a ton of replies, and not a single person was angry. Every single person said, "Thank you." I had CEOs telling me not to worry, and to buy myself a drink, and that they expect mistakes to happen from time to time. Another customer emailed me and said, "I forwarded your note to my entire company because I thought it was the perfect example of how to handle a situation like this."

Everything I've learned from Jason and David at Basecamp has served as a greater reminder to lead by example and with action when it comes to treating customers fairly and being honest. These aren't just platitudes, but things you can and should act on.

There's a cheesy quote about how values don't mean anything until they're difficult to act on, and that has proven itself to be true to me time and time again as a leader. When asking myself the question of what kind of leader do I want to be, I want to be the leader that follows through on what I promise to my team and my customers.

Photography by Northwestern University
There's a cheesy quote about how values don't mean anything until they're difficult to act on, and that has proven itself to be true to me time and time again as a leader. When asking myself the question of what kind of leader do I want to be, I want to be the leader that follows through on what I promise to my team and my customers.

OL: When you think about the landscape of remote work and remote leaders, what are some of the big things that you think are critically important for a remote-friendly or remote-only company to implement?

CL: One recurring thread in all of the conversations I have with other CEOs of remote companies is the importance of being discerning in who you hire. It's a little bit different who you hire in a remote company versus who you hire in an in-person company. There's probably some overlap, but there are two things in particular that always come up when you're hiring remotely.

One is highly self-directed people which, of course, is ideal to hire for in any company. But in a remote company, it becomes even more crucial because this person is in a different office or they're working from home or they're working in a coworking space. You don't have the visual reassurance that there is a butt in the chair and typing going on, and that can cause a lot of insecurity for first-time remote leaders or leaders of remote companies who haven't had exposure to that yet. What I've found in the best remote leaders is they know that they have to start with who they bring in and who they choose to bring on board.

It's also insanely important for remote leaders to hire people who have a high degree of empathy  and the ability to not get personally offended by things in writing. A lot of times what happens at remote companies is important, tough conversations can happen via Slack or email, where it can be uncomfortable for some people to read tough feedback in writing. Other times, written instructions can be perceived as more abrupt or rude than if they were delivered in-person. So it's important for remote leaders to hire people with a generous ability to empathize.

Remote leaders also need to trust their employees. As a successful remote leader, you can't be pinging people in Slack all day or trying to do a daily check-in over the phone. You have to trust your people, and Paul Farnell, the founder of Litmus, has a great quote about this. He simply says, "Trust your team. Work only gets done when you allow people to make mistakes."

Remote CEOs also need to understand the importance of respecting the quiet. They need to understand that people can't get work done if they're incessantly making requests, asking questions, and checking in. Protecting people's time and understanding that is a key function of remote leadership.

Finally, something that's important for all leaders to do – but in a remote company it becomes almost do or die  is to communicate extremely often, and to communicate well.

There's a very tired maxim of saying that you can never over-communicate enough at a company, but at a remote company, nothing could be truer. So many remote CEOs that we work with will talk about how important it is to write up and talk about the mission, new initiatives, and progress – constantly. Because you don't physically see people in-person, information doesn't spread in the same way, and leaders need to do the heavy lifting for evangelizing the message.

It's also important that remote leaders find ways for people to interact with each other in-person  physically, or virtually. A lot of companies think and structure meaningful ways for people to interact with each other both online and offline  whether that's work-related or not. Help Scout, a customer of ours that's a 100% remote team, holds weekly Fika meetings. "Fika" is the Swedish word for coffee, and they'll randomly assign two people to have coffee via Skype or Zoom to chat and get to know one another outside of day-to-day tasks.

Finally, every single remote company I've ever talked to hold some sort of annual or biannual in-person meetup or retreat for all employees to come together, learn, and bond.

Photography by Northwestern University

OL: Do you have any thoughts on remote-only versus remote-friendly companies?

CL: It's very difficult to dip a toe into remote work. David Cancel, the CEO of Drift, has talked about how, when you have some team members with remote privileges and some team members who don't, you create second-class citizens in your workplace. The same goes for if you have in-person meetings, but you haven't created the ability for people to call in and listen or Zoom in.

What the best remote companies do is embrace the idea that you have to commit, one way or the other. Even if you do have an in-person office, this means that when you have a conference call in the office, every single person who's in the office still gets on that conference call as if they were remote, too. If you're just a remote-friendly company, you need to embrace the idea of being remote-first and remote-centric — otherwise, you'll create a real cultural and functional division within the company.

OL: What do you think is the biggest misconception about those who think that remote teams are at a disadvantage?

CL: I completely disagree that remote companies are at a disadvantage. I actually think they're at an advantage because physical proximity is no longer a crutch for communication and for interaction and for idea generation. It means that every single action within your team just has to be so much more intentional, so much more clear, and purposeful. Remote companies have to write better, be more purposeful about who you hire, and be more purposeful about your onboarding process.

These are things that you might do well within an in-person company, but because you're remote, you have to think harder about them. As a result, you're more rigorous about them and as a result, those results tend to be better.

I think the other advantage that comes with remote work is the fact that you can hire whomever you want, wherever they are. You can hire the best person for the job, and they don't even have to move, so you have a huge advantage in terms of the talent pool you're able to bring on board.

I also think there's an advantage for remote companies to carve out dedicated, productive, creative thinking time for their employees. I know that in order for me to do my best work, I need uninterrupted four-hour periods of time to get stuff done, and that's more difficult to get when the company is all working in the same space, versus when you're remote.

OL: What do you envision will be the biggest or some of the biggest shifts to remote work over the next 15-20 years?

CL: I hope that technology will get to a point where it's so good that it's crazy to not work remotely, and I think that will be the biggest shift. The technology today is great, but sometimes it's just not the same as being in the same room as someone and whiteboarding out an idea. There's sometimes really something special and magic about having someone in-person to bounce ideas off of, and, trust me, there's a reason again why so many remote companies make sure to get together in-person from time to time. There's nothing that truly replaces face-to-face communication, but I think that 25-30 years from now, people will laugh at that comment.

OL: How do you think that that will change the way people think about work?

CL: I think the growth of remote work will allow people to live their life on their own terms. When you can work from wherever and you're given the trust to get the work done — instead of always needing to be somewhere at a certain time — more people will be able to eat breakfast with your kids and take them to school. Even if people are working earlier in the morning or later at night, the same amount of work is able to be done.

Maybe people will be able to become more creative and produce better work because they have bigger blocks of time to work on what they want, without being interrupted by other people. So I look forward to seeing more people be able to work on their own terms.

OL: What would be in your playbook for things remote leaders should tackle in 2019?

CL: One is to focus on building trust. Trust something that all the remote leaders who are successful have in common, and it's something that can be very difficult to establish when you aren't able to see someone face-to-face, five days a week.

So, how do you build trust? We ran a survey of 600 managers and employees asking about trust, and the number one way people said that they felt helped build trust was to show vulnerability as a leader. If there's one thing I would suggest to CEOs to try to do to build more trust in their remote teams is to admit what you're struggling with, where you've fallen short, and what you want to improve. Building trust is a great way to start 2019.

Another is to over-communicate and to make what's implicit explicit. As a remote company, it's very difficult to always know what's going on and why decisions are being made. It's hard enough to keep a pulse on these things in-person, so the fact that you're not seeing people face-to-face means you have fewer touchpoints to make sure everyone on your team is on the same page. Make what is so implicit to you as a leader more explicit to your team, so you're communicating your intentions and reasons for the decisions you make.

Upping the frequency at which you're communicating is something any leader can stand to do. If you're repeating things more than you feel like is comfortable, it's probably the right frequency, and you can even do it more. Building trust and making what's explicit implicit are important things to keep in mind for leading a high-performing remote team.

You can never over-communicate enough as a leader at a company, but at a remote company, nothing could be truer. So many remote CEOs that we work with will talk about how important it is to write up and talk about the mission, new initiatives, and progress — constantly. Because you don't physically see people in-person, information doesn't spread in the same way, so leaders need to do the heavy lifting for evangelizing the message.

Key Takeaways

1. Pay attention to the messages your audience is telling you to improve your product and content offerings.

One of Claire's biggest lessons was from changing everything about the company and the product. By paying close attention to blog traffic and their online community, Know Your Company was able to better meet a need for a highly engaged audience that was looking for a solution. The signals from secondary audiences led Claire to change the product and rebrand the company to what it's now known as: Know Your Team.

2. You need to be a good writer to be an effective remote leader.

Claire stresses the importance of writing when it comes to leadership, but particularly remote leadership. Because so much remote communication is asynchronous, it's important to write clearly and effectively so remote team members are able to understand decisions made and priorities chosen.

3. Successful remote leaders make the implicit explicit for their teams.

Along those same lines, Claire believes it's critically important for remote team leaders to communicate until they're over-communicating with their team. Without face-to-face meetings and opportunities for in-person communication, it becomes important for leaders to repeat the mission, the challenges, and the decisions over and over again to make sure everyone is on the same page.

To learn more, read our state of remote work report next.

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