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The Power of Small Conversations

  • May 23, 2026
  • Matt Dickerson

Leadership is often associated with moments where the leader is highly visible. These could be when they are leading team meetings, giving presentations, or when making and sharing major decisions. While those moments matter and often carry weight, they are not where most leadership is experienced by others on a day-to-day basis.

“I Feel Like I’m Missing Something”

I was working with a client I will call Carlos, who led a team of project managers in a fast-paced technology environment. In one of our sessions he said, “I feel like I am constantly in meetings, and yet I do not feel connected to what is really happening with my team.” His frustration was clear. “I get the sense I am missing something about this whole ‘manager’ thing.”

He paused.

“I guess…well, I guess I am getting the impression that I am doing all of the big things right. When we are in team meetings, for example, I think I am showing up well as a leader. We have productive meetings. I am in command of the room, and I think my team feels free to share, debate, and challenge each other and me. But I can’t shake the feeling that there is a part of leading a team that I am missing.”

Carlos was experiencing a challenge to his confidence.

He continued, getting a little more specific about the potential disconnect. “I think I only really talk to people when something is off track, and so most of my conversations outside of meetings are about problems.”

Moving Beyond Status Updates

I nodded and let that sit for a moment before asking, “What do you think could be missing?”

He leaned back slightly and said, “It probably means I am not seeing what is working, and I am definitely not hearing how people are thinking unless something is wrong.”

There was a shift in his tone at that point.

“I do not think I have created many opportunities for just conversation,” he said. “Everything feels tied to an outcome.”

I asked, “How could it be different?”

“I think I want to understand how they are approaching their work, not just whether they are getting it done.”

That distinction became a useful starting point.

“I could probably start by asking a different question,” he said. “Something that is not just about a status update. Maybe something like, what is going well right now?”

I nodded and left space, and he added, “That feels simple enough that I would actually use it.”

He brainstormed a few more questions that he might lean on to encourage members of his team to share more freely.

What Happened When He Stayed Curious

The following week, he came back and said, “I tried that question more than I expected. I actually had a chance to incorporate several of the ones I jotted down during our last time together!”

I asked, “What did you notice?”

He smiled slightly and said, “At first, people gave short answers, and I almost moved on, but then I stayed with it and asked a follow-up.”

I asked, “What did you ask?”

He said, “I asked what was contributing to that, and then they kept going.”

He paused, then added, “Some of those conversations went further than I expected. One of my team members started describing how she had adjusted her approach to a project, and I realized I had no idea that she was thinking that way,” he said. “It was not something I would have asked about in a normal update.”

Creating Space for Perspective

I asked, “What stands out to you about that?”

He leaned forward slightly and said, “I think what I was missing in this new leadership position was perspective, their perspective. Ironically, that is one thing that I appreciate about our time together. I feel like I have space to work through my own thoughts. It occurs to me now that I can do something similar with my team members.”

I nodded affirmatively.

“And I also noticed something else,” he said. “When I asked those questions and did not jump in right away, people started building on their own answers, and in one case, two team members started talking through an idea together without me doing anything.”

That realization shifted something for him, and over the next few weeks, he continued to use small questions in small moments, and he began to see patterns in how his team approached their work, how they solved problems, and how they supported each other.

The Subtle Pull of Credibility Hunger™

What Carlos began to experience is something many leaders encounter, which is the tendency toward Credibility Hunger™, the subtle and ongoing pull to prove value through visible contribution, often by stepping into conversations quickly and directing outcomes, and while that instinct can be useful in certain moments, it can also limit what emerges from others.

As he stepped back, even slightly, he began to see that his value was not only in what he contributed directly, but in what he made possible through the way he engaged, and those small conversations became a place where that shift could take shape.

One Small Question Can Change a Conversation

If you are looking to strengthen your connection with your team, you do not need to redesign your communication approach all at once, and you do not need to introduce a new system or process to begin. You might start by noticing the conversations that are already happening and asking yourself what one small question could shift those interactions in a useful direction.

Ask the question, stay with the response, and see what happens.

Looking to Strengthen Connection and Communication With Your Team?

If you are realizing that leadership is about more than driving outcomes, navigating the tension between directing and listening, or looking for ways to create more meaningful conversations with your team, I’d welcome the opportunity to continue the conversation.

  • Schedule a Call with Matt via Calendly
  • Email us at  matt@mattdickersonvalued.com
  • Connect on LinkedIn and start a conversation

No pressure—just an opportunity to explore how small shifts in questions, presence, and communication can help you better understand your team and create space for stronger engagement, collaboration, and growth.

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