Several weeks ago, I was listening to Dave Perell’s How I Write podcast, and I was inspired by his conversation with David Whyte, who happens to be one of my favorite poets.
For those of you who don’t know David Whyte’s work, it is extraordinary. He is such a deep thinker and explainer of life, and I highly recommend reading his poetry if you want to grow as a person or as a leader. David’s writing is a masterclass in using words to unpack life’s intricacies, and I feel like his poetry so eloquently guides us toward subtle shifts.
During the podcast, David Whyte shared a powerful idea that stopped me in my tracks:
A conversation isn’t just two overlapping monologues.
It’s an exchange where you hear yourself say things you didn’t know you knew.
The moment he said that, I felt something inside me shift.
Because he’s right.
We think of conversations as the back-and-forth of ideas, words, questions, and replies. But the most meaningful conversations – the ones that truly change us – reveal parts of ourselves we didn’t know were waiting to be spoken.
That’s the power of a real conversation.
It opens a door.
It moves something inside of us.
It invites us to speak truths we haven’t yet fully realized.
And if you think back, you’ve likely had moments like that too. Times when you said something aloud and surprised yourself. Times when clarity arrived mid-sentence. Times when the person sitting across from you asked a question that unlocked an insight that had been sitting quietly inside of you – hidden beneath the surface.
This is why conversations matter so much in leadership.
Leadership isn’t just about direction, decisions, or delivering outcomes. It’s about creating the conditions for people to think more deeply, speak more honestly, and participate in the direction, decisions, and outcomes.
When a leader truly engages in a conversation, they help others hear their own wisdom by articulating ideas they didn’t know they had. They also allow teams to uncover clarity that no plan or strategy alone could surface.
A great conversation is an act of leadership because, at its essence, it is an act of generosity. When you create space for someone to hear themselves, you offer them something rare: a moment of genuine self-discovery.
So here’s a subtle shift to try this week:
Enter your next conversation with the intention of discovering rather than proving.
Slow down.
Ask questions that invite reflection.
Sit with the silence instead of filling it.
And listen closely to the moment when the other person says something that surprises even them.
That’s where insight lives, and growth happens.
You’ve got this.
— Matt
P.S. If you want to deepen this idea, read David Whyte’s poem “Sometimes.” It’s a beautiful example of how a few lines can shift how you see your own life.
