Why walk alone?
There's a call from 2019 I still think about.
I was running a startup. An adviser had been assigned to me and on one of our calls he said: "you'll be a good soldier. You'll do what they say."
I'm almost positive he meant it as a compliment. But it had the effect of erasing me.
I got off the call and went back to my desk. Then to my car. I drove around for about fifteen minutes and ended up at a small nature preserve that I knew had a short walking path. Maybe fifteen, twenty minutes of walking. Then I drove back.
Forty-five minutes, total.
What I came back with: I remembered why I was there. Who I was serving. What actually mattered to me about the work and the people in it. The noise from that call and the inner turmoil it stirred hadn't disappeared, but it had found its place — for one, in a Google doc where I jotted down my thoughts during the walk.
I've thought a lot about what happened in those forty-five minutes. And I've watched similar things happen with the leaders I work with. The pause makes something available that simply cannot be accessed in the motion of the work. It's like a return to something you already knew but had temporarily lost access to.
Most high-performing people I know are good at everything except this. I mean it as an observation, and actually not even entirely about them. It's also about the conditions they operate in. Their conditions reward motion. They punish stillness. And so stillness becomes something you do on vacation, or when you're sick, or when you've finally run out of runway, or a job or a relationship. Not something you choose or build into the way you work.
But the walk alone has a ceiling.
What I really needed in that moment was someone to think with. Not a sounding board. Not someone to validate whatever I'd already decided. Someone who could hold my values and my vision with me, and at the same time challenge what I was making of the situation. Ask the harder question. Offer the perspective I couldn't generate from inside my own head.
The pause opens the door. But most leaders are walking through it alone. And there's a version of clarity that only becomes possible when someone who genuinely understands what you're trying to do is in the room with you, or on the other end of a call, asking the question you haven't been able to ask yourself yet.
That's what I do with the people I work with. I call it Critical Thought Partnership and if you've never heard that term, that's fine. What it means in practice is something closer to what that walk was reaching for, but with another mind in it.
If you've been pausing but doing it alone, I'd be curious what you think you might be missing.
About Dave
Dave O'Connor is an executive coach based in Market Square, Lake Forest, Illinois, who works with senior leaders in person and virtually. He holds the ICF PCC credential and is a former president of a private equity-owned company. He coaches founders, CEOs and owners on personnel, product, partner and positioning decisions.
Dave O'Connor, Executive Coach · 253 Market Sq Ste C, Lake Forest, IL 60045 · 518-727-6531 · Mon-Fri 9am-5pm