Trust Isn't Built in Workshops (And Other Things Your Team Already Knows)

It's early 2026, and I see it all the time: managers investing in trust-building activities—escape rooms, personality assessments, team offsites with carefully designed exercises.

And you know what? These can be valuable. I run workshops myself, and when done well, they create space for important conversations.

But here's what I've learned: the workshop is just the beginning. The real work—the trust-building that actually sticks—happens in the everyday moments afterward. In how you respond when things go wrong. In whether you practice what the workshop preached.

You can't outsource trust-building to a single event. It grows in the margins, the mistakes, the moments when things don't go according to plan.

The Opportunity I Miss (Almost Every Day)

Last week, someone on my team completely missed what I was asking for in a project brief. And my first instinct—I'm not proud of this—was to ask "Why didn't you just read what I wrote?"

I caught myself. Barely.

What I asked instead was: "What happened? Walk me through how you understood the brief."

Turns out, I'd been vague in three different places, used a term that meant something different to them, and assumed context they didn't have. The misunderstanding was at least 50% my fault.

If I'd gone with my first instinct—"Why didn't you read this properly?"—they would've gotten defensive, I would've gotten frustrated, and we both would've walked away thinking the other person was the problem.

This is where trust actually lives. Not in the big moments, but in the split second between something going wrong and your response to it.

"What happened" opens a door. It says: I'm curious, let's figure this out together, I might be missing something here.

"Why did this happen" closes one. It says: defend yourself, I've already decided you messed up, convince me otherwise.

The real opportunity: The next time something goes wrong—and it will, probably today—catch yourself. Notice which question wants to come out of your mouth. Choose the other one. It's harder than it sounds.

The 4pm Friday Email I Actually Sent

A few months ago, I spent three weeks pushing the team toward a particular approach for a client project. I was convinced it was the right direction. Made a whole presentation about it.

Thursday afternoon, I finally sat down to actually work through the details myself. And within 20 minutes I realized: this isn't going to work. The approach had a fundamental flaw I'd somehow missed.

I had two options:

1. Say nothing, spend the weekend trying to salvage it, quietly pivot on Monday and hope no one noticed how much time we'd wasted
2. Send an email admitting I'd steered us wrong

I sat there staring at my laptop for a solid 10 minutes. Option 2 felt like admitting I had no idea what I was doing. Like I was undermining my own credibility.

But I sent it anyway: "Hey team—I've been thinking about the approach I've been pushing for the past few weeks. I think I was wrong. Here's what I'm seeing now..."

What actually happened surprised me. Two people replied within the hour saying they'd been worried about the same thing but didn't want to push back on me. One person said they were relieved because they'd been trying to figure out how to make it work and couldn't. And on Monday, we had the most productive strategy session we'd had in months because everyone felt like they could say what they actually thought.

Nobody lost respect for me. If anything, it got easier to have honest conversations after that.

The real opportunity: Find something you got wrong this month—not something catastrophic, just something you called incorrectly. Tell your team about it before the week ends. It's going to feel uncomfortable. Send it anyway.

Your Move

Pick one: the question you ask when things go wrong, or the admission you've been avoiding.

Not both. Just one. This week.

I'm working on the first one myself—catching that split second before I respond when something goes sideways. Some days I get it right. Some days I don't. But I'm getting better at noticing.

Trust isn't built in workshops. It's built in moments like these—the ones we choose, over and over.

Next up: "The Meetings Where Trust Actually Happens" (or doesn't). Because that weekly team meeting everyone zones out in? Yeah, we need to talk about that.