Building Trust with Your Leadership Team: Candid Debriefs

Let’s talk about the moment when the air in a room finally changes. You know it. It’s after two hours at a leadership offsite. People have stopped looking at their phones. Someone finally says what everyone’s been thinking, out loud, in their own words. It’s rarely pretty. But that’s where trust actually starts.

I saw this play out again last quarter, holed up in a Colorado cabin with four VPs, two directors, and enough cold brew to fuel a hackathon. Day one, everyone was polite. We rehashed wins, walked through initiatives, and sipped coffee. It felt productive, but stale. We’d all heard these updates on Zoom the week before.

What pushed things forward wasn’t a new framework or fancy offsite agenda. It was a few pointed questions - and the collective willingness to own our misses.

By late afternoon, I had the team circle up and do a candid debrief. I didn’t lead it. I sat down and asked, “What’s REALLY working here, and what are we all avoiding?” I shut up and waited. Somebody cracked a joke. There was a long pause. Then the mobile lead called out a process problem that’d been quietly annoying his team for months. The head of product winced and admitted he’d stopped following through on sprint reviews. Slowly, the walls came down. We spent 90 minutes poking holes in our own habits, talking about where we’d let each other down - and where we needed help to get better.

Here’s the thing. Teams don’t get stronger by glossing over the ugly parts. Trust gets built every time people put the real issues on the table and take real ownership for fixing them. Most offsites are filled with pep talk and vague feedback. That’s polite, but it kills momentum. Your team sees right through the performance.

I see this play out every time I visit an R&D team or sit with product leaders at a whiteboard. The difference between a group of leaders who trust each other and a group who don’t? It’s all in how they debrief - their willingness to open up, even at the risk of looking foolish. Weak teams trade in updates and data; strong teams deal in candor and humility. If you want your team to run faster, you have to take the risk of going first. Share where you messed up. Invite input and mean it. Say what you’re struggling with, and ask the team for help. That’s how you get people to drop the act and start solving real problems together.

I’ve had the privilege to coach execs at some wildly successful SaaS companies, and the same pattern always shows up. When leaders hide behind “everything’s fine,” trust evaporates. When they drag issues into the sunlight, admit their own missteps, and ask for input? The team starts moving together - faster, clearer, looser. Ownership isn’t about defending your turf. It’s about looking across the table and saying, “Here’s what I missed. Here’s what I own. Can you help me get better?” The best leaders I’ve worked with have the guts to show vulnerability first.

So if you want a team built on trust and real momentum, skip the surface-level retros. Bring your leaders together and ask the uncomfortable questions. Make debriefs a habit. Model what ownership looks like. Open yourself up to input - and actually listen. Your team doesn’t need more polish. They need realness and permission to be candid.

Next time you’re with your leadership crew, pay attention to the energy in the room. When do people lean in? When do they tune out? If you want real buy-in, show them what honest debriefing and true ownership looks like. You don’t need to be perfect. You just have to be real.

That’s where trust begins - and momentum actually lives.