In early July, I lost one of my closest friends from college, Louisa, in a bike crash. She was killed by a truck while riding to work, where she fought tirelessly as a city planner and transportation advocate to make Boston's streets safer for cyclists, pedestrians, and drivers alike. She was a light in the lives of so many and leaves an enormous void behind.
Of the many things I admired about Louisa, her curiosity made me marvel the most. I loved looking at what caught her attention, what she took pictures of, and what she said to people she disagreed with.
We moved through the world differently. I rarely take pictures and am often thinking about my to-do list instead of what's right in front of me. I also tend to go inward when conflict shows up unless I am completely comfortable, but Louisa was the opposite. She photographed what most people walked past: a tree, my preschooler's Santa swim trunks hanging to dry, the way light hit a building, a drooping plant. When someone disagreed with her, she didn't become defensive, she became interested. She asked another question, not to convince them they were wrong, but because she genuinely wanted to understand.
When I first began my coaching course work, I loved telling Louisa what I was learning. My mentors talked about the importance of curiosity and said “We can never be in someone else’s shoes unless we ask more about their experience.” I remember telling Louisa about this at a picnic we planned at Cambridge Common. After listening intently she smiled and said “I have so many questions.” We both laughed and continued talking.
As I practiced coaching, I found myself borrowing Louisa's way of seeing people. Before assuming I understood someone's experience, I'd ask another question. Over time, I noticed something surprising. The leaders who came to coaching rarely lacked answers. More often, they had become trapped inside the first explanation they had given themselves. I'm burned out. I'm not ready. I need to leave. I'm failing.
Curiosity slows that sense of certainty down. Instead of asking, "What's the solution?" it asks, "What's really happening here?" Instead of assuming we already know the story, it reminds us there may be another one waiting underneath.
Questions like:
What am I so busy trying to solve that I haven't stopped to understand?
What assumptions am I making that might not actually be true?
What would I notice if I approached this moment with curiosity instead of judgment?
Louisa lived this way instinctively. She noticed my son’s silly Santa swim trunks and the drooping plant. She kept and displayed the postcards she’d collected over the years. She genuinely wanted to understand the person she disagreed with. She paid attention. I’ve come to realize that’s what the best leaders do too. Not because they have the quickest answers, but because they stay curious long enough to realize they might be asking the wrong question.
I don't think I'll ever see the world quite the way Louisa did. I still catch myself rushing through my day, thinking about my to-do list while playing with my kids, and likely missing things Louisa would have stopped to admire. But now I notice when I'm doing it. She taught me that curiosity isn't passive, and that there will always be more to understand. I've watched this perspective change my conversations, open up the eyes of the leaders around me, and slowly I’ve watched it change me. Maybe before we can lead anyone or anything else, we have to be willing to look a little longer, to ask another question, and to resist believing we've already understood.
Because the moment we think we've seen everything is often the moment we stop noticing what matters most, silly Santa swim trunks and drooping plants included.
