A Practical Lesson I Learned During My Hedge Fund Days

Almost eight years ago, I worked as a chief of staff to a management committee at one of the world’s largest hedge funds. While the experience overall was both memorable and formative, there is one particular day that continues to stand out to me.

Instead of huddling together inside the walls of the firm’s Connecticut headquarters, my boss asked me to meet him at a restaurant in NYC. What a treat! Having never actually spent a day working in the Big City, let alone at a hip West Village restaurant, I felt grateful for a reprieve from our traditional routine.

But, what I remember more about that day than anything else was what we did. We spent hours working on how to structure his calendar.

Synthesizing the different types of work he would regularly engage with into high-level buckets, thinking through how his brain was more or less capable of solving different types of problems at different times of the day. We came up with what we called a “hard structure for the week”. We defined when it was OK to block meetings, when he should engage in heads-down work, and when he should handle tactical must-dos. I was surprised that someone in his position was keen to spend so much time figuring out how to do something as basic as manage his calendar.

It wasn’t long before I realized that time is a senior executive’s most precious commodity. And, how effectively you spend your time can make all the difference. 

When Scouted first transitioned into a remote work environment, I made some changes to my team’s overall hard structure, but I also kept a lot of it the same. For instance, every Tuesday morning we run weekly OKR meetings and after the meetings we kept our tradition of doing a team lunch. Four months into shelter-in-place, I’d been following the same routine and week after week I had this guilty feeling of dread. Instead of looking forward to those team lunches, which used to be a reward, they felt like a chore. And I realized that, after two hours of sitting in front of the Zoom screen, the last thing anyone wanted was to spend more time in front of their screen. I needed a break.

And, after asking my team, it turns out we all needed a break. 

And so, just last week I made a small change to my team’s hard structure. I moved our team lunches to Monday. It’s a way for all of us to be together at the beginning of the week, remind ourselves that we are part of a broader community, and to catch up on the weekend. And, perhaps most meaningfully, I instituted “No Meeting Wednesday”. Not only does this give everyone the opportunity to make real progress on their goals, but it also makes the week feel much less intense and tiring.

It took me a while to realize this, but when all our meetings are in front of a screen, it creates fatigue that is different from when we are all together in person. I can’t tell you how these simple changes to our weekly hard structure have made all the difference. My team is more excited to be on a Zoom call when we are all together; they are more energized and they feel like they have more time to accomplish their goals. Interestingly, they have the same literal amount of time available to them in the week, but the small changes we made as to how our time is structured, have made a substantial difference to our overall work environment. 

And now, that exercise of integrating understanding and empathy for what we, as individuals, need to do our best work into how we structure our time has proved to be a key driver of my employees happiness and productivity. 

As business leaders, we are all learning in real-time about how previous best practices might need to be adjusted. Now that many of us are going to be working remotely for the foreseeable future, I encourage us all to evaluate the structures we have in place to see what needs to change.

Because, as much as things might feel the same, they really are materially different.