The Importance of Versatility
When we caught up with John Cowan for our latest in the Lieutenant series, we should’ve known we would walk away feeling a little less…lost. John is currently the vice president of finance at Tile, a company whose mission it is to find everything that matters. In our chat, we discussed how his quiet curiosity and varied interests (wait until you see what he studied in college) have led to a versatility that has served him well over the years, allowing him to step into diverse roles professionally. We also talked about how, while mistakes are inevitable in any organization, operating from a place of empathy, with a "healthy sense of paranoia" and a growth mindset can create a path for success.
Can you tell us about your role at Tile?
When I joined Tile two years ago as the head of strategy and business operations, I spent a good chunk of that time on fundraising, eventually raising $45 million in our Series C. After that I took on a completely new role in product, which is an area that was completely new to me. After successfully launching a new tier to our subscription product, called Premium Protect, which has really good traction, I'm now taking the reins of our finance team.
I started my career in finance and investment banking so it's a natural move, but having the opportunity to step into different roles, to solve different problems and learn new areas along the way has been inspiring. I take pride in being versatile, and having both a depth and breadth of experience that I’m constantly looking to grow in both directions. I think versatility is really important, especially in growth companies. Being able to step into different roles and fill gaps where needed is essential, especially in a company that is always evolving and must operate with an “all hands on deck” mentality.
I think versatility is really important, especially in growth companies. Being able to step into different roles and fill gaps where they’re needed is essential, especially in a company that is always evolving.
Have you always had that Swiss Army knife-like versatility in your career? Or is that something that's evolved more recently?
I think it's always been there. I've had varied interests throughout my life. I majored in economics and minored in evolutionary biology, which are completely different from one another but equally fascinating. A significant personal mantra is to listen and learn. I go into every situation looking to learn as much as I can no matter my I going knowledge base, never assuming that I know it all.
What are 2-3 characteristics of great lieutenants?
I look for people who choose to "know, rather than assume." As a lieutenant, you have to dive deep into the details, and are filtering a ton of information. It's easy to take shortcuts and make assumptions, but it's those details that ladder up to execution, which ladders up to the long-term strategy, so it’s important to get the baseline right. Don’t assume; know.
I look for people who choose to "know, rather than assume."
The second area is the ability to align and communicate well with people across the organization. As a lieutenant, you're on the front lines, which means you're doing both the high level strategy as well as some of the detailed execution. Having that alignment with your executive team, with the board, and with the people you work with cross-functionally is really important.
Lastly, professionally and personally, is empathy. At Tile, one of our values is “better together.” To me this has to do with empathy. There's always stress associated with work, but that’s been compounded in today’s environment. Empathy has never been more important.
Do you have tips and tricks that make you, personally, an effective lieutenant?
One is that I don't let things slip, even the seemingly “little” things. I remember my first job out of college, I was so green and very dependent on my checklist and trying to be organized. I remember to this day, there was this one action item I needed to do and I just didn't do it, to the point where it made me late on a project. It seemed like such a little thing to me at the time, but the lesson I took away from that is that even the small things can be really important.
It's going to sound a little bit funny, but I also think having a sense of healthy paranoia helps. “Healthy paranoia” is about looking at problems from different angles and questioning your assumptions over time. A lot of times we make assumptions based on what we knew at the time, but then we don't go back and revisit them. Going back to review data, to question, to look at the corner cases and understand how things play out is really important. It'll give you and others confidence that you're on top of things. It can be paralyzing to question everything, all the time, so there is certainly a middle ground here. But for me, it’s about wanting to make sure that things get done right.
Healthy paranoia is about looking at problems from different angles and questioning your assumptions over time. A lot of times we make assumptions based on what we knew at the time, but then we don't go back and revisit them.
What do you look for when you hire and build your own team?
I love people with untapped potential, which is a difficult thing to assess in interviews. However, I look for people with curiosity and a desire to learn. That can be even more beneficial than being able to regurgitate a bunch of facts. I also look for people who are passionate, empathetic, and concerned about what the user experience is within the company. Finance, for instance, is a service function and I look for people who think of it in that way. In short, it's a combination of growth potential, desire to learn, and a service mindset.
A lot of the things that I've done, I've learned through apprenticeship models. Certainly on the finance and investment banking side. You learn through repetition, experience, and from making mistakes. You try to prevent them, learn from them, and not let them define you. It's ultimately what gives you pattern recognition.
You learn through repetition, experience, and from making mistakes. You try to prevent them, learn from them, and not let them define you. It's ultimately what gives you pattern recognition.
How do you foster that learning mindset in an organization?
The most critical thing is to allow people to make mistakes. If you have an organization that doesn't allow for mistakes, or if people are hesitant to come forward with problems because they're afraid of what the consequences might be, it's a bad thing. It doesn't enable versatility or growth. Allowing for mistakes is critical, but it's even more important that you learn and grow from those mistakes. That's what makes the real difference. We do retrospectives a lot at Tile because we want to learn what didn't go well and get better over time. From an organizational perspective, that's important, but it's also important for individuals to have those frank conversations across teams. For big projects at Tile, we might have three, four or five retrospective sessions.
The most critical thing is to allow people to make mistakes. If you have an organization that doesn't allow for mistakes, or if people are hesitant to come forward with problems because they're afraid of what the consequences might be, it's a bad thing.
What is something you're most proud of over the last year?
I’m really proud of the product role I took on. I was nervous at first to move out of my comfort zone. I think a lot of people refer to Carol Dweck's book about having a growth mindset, but it's really difficult when you're proficient at something to move into an area where you might fail. It certainly was for me. It was a new challenge to go from a finance and transactional partnership background to step into something that I've never done before. But being a part of this new product release from soup to nuts -- defining it, securing a partner, releasing it, all these sorts of things -- was really rewarding. It also gave me the opportunity to build personal relationships and trust with people across the organization who are experts in what they do.
It's really difficult when you're proficient at something to move into an area where you might fail.
What do you love about working for your CEO, CJ Prober?
I've worked for and with CJ for five years, and he's an incredible leader. He's not only whip-smart, but also practical, passionate, motivating, empathetic, and just incredibly hard working. I want to work for a leader who leads by example and CJ does that. He sets the tone for the organization, and is willing to empower Tilers to achieve their full potential. We talk about the importance of allowing for mistakes and he enables that. It's a tough balance to challenge others to grow while maintaining focus and executing, but CJ does that in a really fantastic way.
Do you serve a role as a contrarian to CJ?
I would say we serve as contrarians to each other. CJ, like I said, facilitates an environment where you're able to bring problems, admit mistakes, and voice opinions. I think if you have a group of employees and colleagues who are always agreeing with you, then you're likely not getting to the best answers.
I think if you have a group of employees and colleagues who are always agreeing with you, then you know you're doing something wrong.
How do you want people to describe your professional legacy in the future?
For me, it would be, "That guy was always learning." If I get to the end of my career and someone says that about me, I'll be happy. I'm more of a quiet learner by nature, and like to approach every interaction as an opportunity to be curious and listen. If you fall into the trap of thinking you don't need to continue to learn, it's going to be a bad outcome.
