The Loneliness of the Flawless Leader
How to Build a Connected Team in a Virtual World
I’ve been lucky to be able to work in a variety of environments and configurations. Sometimes, I was a member of a working group. I always thought of this as driving on the highway - we were all in different cars, but headed in the same direction. Sometimes, there would be too many of us trying to use the same resource at the same time and it would create a traffic jam, but for the most part, we were all able to make progress at our own pace. Other times, I was part of a team, where we moved together, on a bus or subway car.
At one organization, we all had our own partners to manage. In this mission-driven non-profit, we all were aiming at a goal of high social impact, and we were all high-performers. But because each of us was responsible for our own specific area, we lived in parallel silos. We could troubleshoot or brainstorm with one another, but we couldn’t really share the load.
The result? Even in a room full of people, it could end up feeling incredibly lonely.
The Loneliness Epidemic at Work
We are currently living through what researchers call a Loneliness Epidemic, and virtual work has, in many ways, thinned the threads that connect us. It’s easy to feel like your silo is your entire world. But when we expect our workplace to solve 100% of our need for connection, we put an immense burden on our professional relationships.
One way to alleviate this is by looking at our social responsibility (our willingness to contribute to the welfare of others) both within our working roles and beyond the office walls. Whether it’s volunteering or joining a community group, contributing to life outside of your job makes you a more well-rounded person. It helps you see yourself as a single, important piece of a puzzle rather than the whole puzzle itself. By zooming out, you begin to build your empathy muscle as you are exposed to different perspectives, which you then bring back to your team.
From Silos to Shared Margin
Most of us want to move away from these silos. We long to be in places where each person brings their best and can trust the others to do the same. But relying on others is a hard bridge to build, especially in virtual environments.
In my experience, the bridge isn’t built by a bigger budget or a better project management tool. It’s built by intentionality and empathy. I saw this modeled extremely well by a Director that I worked under. He set up a weekly team call where the primary focus was hearing about each other’s weeks and what was going on with each person personally. People were free to share with whatever amount of vulnerability felt right to them. While we chatted about little things and big things, we were building our ability to empathize with one another and gaining trust. That empathy and trust created margin. Once we knew what someone was actually up against, we were able to stop giving simple advice and start stepping in to help carry the weight.
The Four Sentences That Build the Bridge
The biggest barrier to this kind of team is the pressure we feel as leaders to be flawless. We think we have to have every answer. But empathy requires a catalyst: vulnerability.
I’m reminded of Louise Penny’s character, Chief Inspector Gamache,1 who says there are four sentences that lead to wisdom:
I don’t know.
I need help.
I’m sorry.
I was wrong.
In your silo, “I need help” might feel okay, but “I don’t know” feels like a risk. Yet, when you say “I don’t know,” you aren’t showing weakness; you are creating an opening for someone else to bring their strength to the table. You are moving from the mentality that you have to do it all alone to prove your worth to doing it together.
Reflect and Act On It
Reflect: Think about your current team. Are you a group of people working in parallel, or are you creating margin for one another? Which of the Four Sentences feels the scariest for you to say out loud?
Act: This week, instead of jumping straight into the agenda of your next meeting, take 30 seconds to observe the room. Try to name the dominant emotion you sense from one or two people. Then, try one of the Four Sentences. If a project is confusing, say “I don’t know the best path here, what do you think?”. Watch how quickly that “silo” starts to open up.
The Inspector Gamache series is amazing. If you haven’t read it, do yourself a favor, go to the library and check out the first book - Still Life. But be prepared, the series is sitting at 20 books today!




I enjoy reading your content God Bless You.