Trust Doesn't Break in Big Moments—It Leaks in Small Ones

I worked with a founder after they lost a multi-year deal. It wasn't a dramatic failure—no botched demo, no pricing mishap, nothing that would make for a cautionary tale at a conference. They lost it because they took too long to answer a superintendent's question.

Five days. That's all it took for trust to quietly walk out the door.

After four decades in this business, I've watched hundreds of deals succeed and fail. I've seen products win that probably shouldn't have, and brilliant solutions lose to inferior competitors. And here's what I've learned: Trust doesn't blow up in the big moments. It leaks out in the small ones.

The Follow-Up You Meant to Send

Early in my career, I thought leadership was about the big calls—the strategic pivots, the major client presentations, the decisions that would shape the quarter. I prepared obsessively for those moments. I showed up ready.

But I missed follow-ups. I let small commitments slide. I'd tell someone I'd get back to them by Friday and then let it slip to Monday. In my mind, these were minor infractions. The person would understand. They knew I was busy.

Except they didn't understand. What they understood was that my word wasn't reliable when it wasn't convenient.

Trust doesn't care about your intentions. It cares about your patterns. And patterns are built in the moments you think don't matter—the response time when you're swamped, the clarity you provide when you're still figuring things out yourself, the expectation you set even when you'd rather stay vague.

People don't need perfect leaders. They need reliable ones.

Predictable Doesn't Mean Boring

I've heard founders push back on this idea. "I don't want to be predictable," they tell me. "I want to be dynamic, responsive, adaptable."

Here's what they're missing: People trust leaders who are predictable—not boring, just predictable. When your team knows what to expect from you, they stop second-guessing and start moving forward.

I've seen founders build incredible momentum simply by showing up the same way every week. Same transparency about what's working and what isn't. Same response time to questions. Same willingness to admit when they don't have all the answers yet.

Consistency isn't flashy. It won't make for a great keynote story. But it's what gives your team the confidence to take risks, because they know you'll be there the same way tomorrow that you were today.

One of the EdTech founders I work with now sends a Friday update to his team every single week. Not when things are going well. Not when there's big news. Every week. It's three paragraphs: what happened this week, what's coming next week, and where he needs help.

His team told me they plan their work around that update. They know it's coming. They trust it will be honest. That predictability has created psychological safety that no trust fall exercise or team-building retreat ever could.

The Dozens of Small Decisions

Your credibility isn't built in the big decisions—it's built in the dozens of small ones you make every day. The promise you keep to your team even when you're buried. The hard conversation you don't put off. The update you send when you said you would.

I've worked with enough founders to know that strong leadership isn't about grand gestures. It's about doing what you said you'd do, especially when no one's watching.

A few years ago, I was advising a founder who was trying to close a district deal while simultaneously managing a product pivot and a hiring crisis. Everything was on fire. During one of our calls, he mentioned he'd promised his head of sales a conversation about expanding the team, but he kept pushing it off because "bigger priorities" kept coming up.

I asked him how long he'd been pushing it off. Three weeks.

"What do you think that's teaching your team about what matters?" I asked him.

He got quiet. Then he said, "That they don't."

The next day, he had the conversation. The team expansion didn't happen immediately—there wasn't a budget for it yet. But his head of sales told me later that the fact he kept his word when everything else was chaos was the moment she decided to stay long-term.

What Small Thing Are You Letting Slip?

Here's the hard part: You probably already know what you're letting slip.

Maybe it's the follow-up you've been meaning to send for two weeks. Maybe it's the expectation you haven't clarified because you don't want to have an awkward conversation. Maybe it's the commitment you made to yourself about how you'd show up for your team, and somewhere along the way, "busy" became your excuse for being inconsistent.

The thing about trust is that you can't rebuild it in the big moments. You can only rebuild it the same way you lost it—in the small ones.

I'm not suggesting you need to be perfect. I've blown plenty of small commitments over the years, and I'm sure I'll blow more. But I've learned to catch myself faster. To own it when I drop the ball. To make the pattern matter more than the exception.

Because at the end of the day, your reputation as a leader isn't what you say in the all-hands meeting. It's what you do in the hundred small moments between those meetings.

The Trust You Build Today

If you take one thing from this, let it be this: The trust you're building or losing today won't show up in this quarter's metrics. It's showing up in whether your team brings you problems early or hides them until they're crises. It's showing up in whether your clients feel like they can count on you or whether they're hedging their bets.

And it's showing up in dozens of small decisions you're making right now that don't feel like they matter.

But they do.

What small promise will you keep today?