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We interview Shane Emmons, CTO of TeamSnap, about his decade of remote management experience and how he builds trust in his team.
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When we think of empathetic leaders, Shane Emmons comes first to mind. He’s the Chief Technology Officer at TeamSnap, where he leads a fully distributed engineering team for the world’s top sports team management software. Shane has been managing teams remotely for almost the decade and stresses the importance of high EQ.
Many remote managers are struggling to build relationships and company culture without in-person interactions. We thought we’d sit down with Shane to ask about his CTO journey and how he builds trust at TeamSnap.
I wake up and do some combination of coffee, biking, walking, and showering before sitting down and doing my morning email triage. Once that is done, I usually have two hours for deep work. This is where I spend time writing articles, memos, recommendations, etc. Our distributed structure at TeamSnap sets aside the core hours of 12-4 ET for meetings so I usually settle in. They range from company-wide status updates to direct report 1:1s to initiative strategy meetings to technology and product roundtables––I have a cornucopia of appointments each day. I spend the last hour of my day doing my evening email triage. Given my hectic schedule, I rely heavily on offloading my memory to various software tools: Todoist for managing all my work, obligations, and commitments; Superhuman for email triage; Ulysses for writing; and Tot for note-taking.
When I’m not working? I’m probably cooking or doing something with my kids. I try to get outdoors. I’m reading a couple of books right now: Amy Poehler’s autobiography and Team of Rivals.
I reject the word “balance,” I prefer the phrase “work-life harmony.” It’s been more acute during COVID, especially when you’re working remotely. The idea of balance is challenging. The lines of work and not-work are blurry. This blurriness drives work freedom, and the goal is to harmonize the two.
I knew I was going to be a computer programmer since kindergarten. My dad performed data analytics for the Navy and taught me about computers before I started school. I went to the University of Michigan and started the Comp Sci program, with a brief flirtation with philosophy. When I graduated, the university began offering a Comp Sci masters degree, and I thought, why not?
At TeamSnap, I skipped a few traditional levels of management. I went from Engineer to CTO without ever managing people. I missed much of the experience I would’ve gotten from a typical trajectory. When I hit CTO, I thought it was more of a technical job than a people manager job. That’s not the case.
When I hit CTO, I thought it was more of a technical job than a people manager job. That’s not the case.
I started my MBA shortly after becoming CTO. There was a point where I felt inadequate compared to other senior leadership on the team. Standard imposter syndrome you get in a new role. I started looking into my peer’s backgrounds and saw many had MBAs. I figured an MBA could get me up-to-speed as an executive. Around this time, I also started working with an executive coach. My coach was the person who first taught me about full-spectrum EQ.
Now I manage a growing team and moonlight as a lecturer at the University of Michigan.
A quarter of my MBA was about operations. Half covered how to be a strategic executive. The last quarter was on organizational leadership. I learned how to organize teams and motivate people, and that’s when you start to learn about yourself. You have to know about yourself first before you can lead others.
EQ is what some would call the platinum rule. It’s about meeting others where they are.
We grow up with the idea of the golden rule: “Do unto others as you want to be done unto yourself.” EQ is what some would call the platinum rule. It’s about meeting others where they are. In the MBA program, there was an entire course about understanding yourself on a deep level and how you use that personal reflection to understand and connect with others. If you’re going to be an effective executive, you need to have a highly nuanced EQ.
I think some of my first struggles were about learning to connect with people authentically. I’d like to think I do that naturally, but I don’t. I have to communicate with anybody and actively cultivate relationships with everyone to get beyond the surface level and coach. You genuinely have to care about everyone to be effective.
You genuinely have to care about everyone to be effective.
Nowadays, the hardest thing I deal with is guiding people to become comfortable with change. It’s hard from two aspects: 1) you can only push people so hard, and 2) people resist change, but you can’t let the organization stagnate. That’s the biggest struggle, getting an organization to get past its institutional muscle memory.
First off, it’s essential to distinguish remote and distributed. Remote is where you work. Distributed is how you work. Distributed work requires trust; remote requires an internet connection. TeamSnap is a distributed team that happens to work remotely.
Part of our distributed nature means that we trust people.
A guiding principle for TeamSnap is that we assume teammates are always acting in good faith. In a remote setting, you’re often by yourself, and human bias tends to presume bad intent. We think of worst-case situations. Part of our distributed nature means that we trust people. Any time we come into conflict, we have to assume they were acting for the right reasons. Anyone can say they trust each other, but you have to practice this skill.
For the first few months of COVID, there was much imbalance. All companies were in crisis mode and needed to make sure everything was stable. I remember explicitly using the analogy of balance and scales, and saying, “We need to put our collective thumb on work.” So we did.
We failed to remind ourselves to slow down. We forgot to take a step back and breathe a little bit. Honestly, it took me recognizing that I needed a vacation to reconnect with family before I thought about my direct reports. I realized what a powerful reset vacation was for me and encouraged the same break for my team. Even with my encouragement and leading by example, it took me taking a second vacation for people to trust that it was okay to take a break. As a team, we learned that we have to look after each other because we do not always notice our mental health.
About a year ago, we introduced the concept of passing the ball.
There was also a misconception that TeamSnap’s value of ownership meant we don’t drop balls when it came to burnout. Many teammates felt this pressure, thinking they couldn’t ask for help. About a year ago, we introduced the concept of passing the ball. We don’t drop balls because we know when to pass it. We are now pretty good at noticing burnout and saying, “I need to pass this ball.”
The first step is to sit down and listen to your people. Actively listen right away and figure out what makes them a person. Learn how your direct reports best receive information. It’s unlikely someone will be completely candid with you right away. You have to build a relationship. You can’t skip that process either, so don’t immediately set up performance metrics. Take the time to build a relationship.
