The Power of 100 Small Conversations
How Shoulder-to-Shoulder Leadership Builds Trust
By Tyler Head
If you lead people, you’ve probably felt this. The moment presents itself—a quick follow-up, a check-in, a question you could ask—and instead, you move on. Not because you don’t care, but because you’re busy, unsure, or it feels a little awkward. I’ve done it too.
But those moments aren’t small. They’re where trust is built—or slowly lost.
In leadership, we often find ourselves bracing for the “big” conversations—performance reviews, compensation discussions, conflict resolution, or misalignment that’s gone unaddressed for too long. To be clear, those conversations matter. They help teams align, define expectations, and measure progress.
But they were never designed to carry the weight of trust on their own.
Trust may be the single most important factor regarding relationships within your organization….But don’t take it from me.
Research continues to point to the same reality: trust isn’t a “soft” leadership trait—it’s a performance driver. A study from Harvard Business Review found that high-trust organizations experience significantly higher engagement, productivity, and retention. Google’s Project Aristotle identified psychological safety—built on trust—as the single most important factor in team effectiveness. Brené Brown’s work on leadership and vulnerability continues to show that trust is built in small moments—through consistency, reliability, and presence over time.
Here’s what I’m learning: the “big conversations” most leaders brace for is often the result of a year of missed smaller ones. It’s also why those conversations so often fall flat. Often times we wait for the moment when something can’t be ignored. When what’s needed and wanted is consistent engagement.
Last fall, I had the opportunity to crew one of my good friends through his first 100-mile trail race. We had a crew of five. I was slotted to join him around mile 35 and run with him through the evening, pacing him to mile 62.
When I met him, he was in rough shape, not physically but mentally. He had gone out fast. At that point in the race, he and two other runners were leading a field of more than 75 racers. By mile 35, it was catching up to him.
We refilled water, grabbed food, changed socks, packed gear for the night, and headed out. Almost immediately, we hit a long climb—over 1,500 feet in six miles. We just kept chugging. One step at a time.
As we moved, he kept saying: “I’m exhausted. I don’t know if I can do this.” I listened, sometimes responding, and sometimes redirecting – to things around us, his training, and other things that came up. I encouraged him to take another bite of food, another sip of water. At one point, I said, “Sheesh, look at that bald cypress to our right—that thing is massive. I wonder what stories that tree could tell.” Then it was back to the basics: take a sip of water, eat something, let’s take a few more steps.
Over the course of 26 miles together, we climbed more than 4,000 feet of elevation, consumed over 5,000 calories, and had dozens of small conversations—moments where I listened, redirected, encouraged, and challenged the narrative running through his head.
Then, somewhere around mile 55, he broke. He sat down, unsure if he could take another step. And we had a meaningful conversation in that moment. The kind that feels big. Really big.
But here’s what struck me later: that conversation only worked because of the dozens that came before it. The steady reminders, the small redirects, the quiet encouragement—it was indeed a big conversation paved by a series of small ones.
This is what I mean by shoulder-to-shoulder leadership. It looks less like delivering answers and more like walking alongside someone as they keep taking steps. It’s stepping into the moment with them—helping them see clearly, wrestle honestly, decide what’s next, and take that step knowing you have their back.
In the workplace, this doesn’t require more meetings. It requires more awareness. Leadership isn’t just about the conversations we schedule—it’s also about the ones we choose in the moment.
It shows up in small, practical ways:
A three-minute follow-up after a meeting when something felt off,
A quick call to check in, or
Naming something someone did well right when you see it.
Small, consistent, present.
Most of the time, you’ll feel it—that moment of hesitation. The thought that this might be awkward, or that you’re not quite sure what to say. It’s subtle, but it’s there, and more often than not, we take it as a signal to move on.
But it’s not a signal to move on. It’s a moment to lean in.
Because over time, the cost of avoiding those moments is real. It shows up as mental energy spent replaying conversations, emotional stress that lingers longer than it should, and a slow drift in relationships that’s hard to notice until it’s already created distance. Eventually, it leads to a “big conversation” that feels heavier than it needed to be.
The conversations we schedule—goal setting, reviews, check-ins—create clarity. They matter. They give direction and help define what winning looks like. But the conversations we choose in the moment—the quick follow-ups, the honest check-ins, the small redirects—are what build the trust that make those conversations actually work.
The posture of leadership happens in both lanes: the conversations we plan and the hundreds of little ones we step into.
As you think about your leadership this week, consider where you might be relying on the big scheduled conversations to do work that really presence, curiosity, and consistency could make much more impactful. And challenge yourself to seize a small moment a simple encouragement, a redirect, and a reminder that you have their back.
Trust isn’t just built in big moments. It’s built in small, consistent conversations over time—the kind that happen when you choose to stay present, step in, and move forward shoulder-to-shoulder, one conversation at a time.
