I sat in on a meeting about a month or so ago with a business owner I deeply respect. It’s stayed with me ever since – something about that room felt not quite right, and it took me a while to put my finger on exactly what.
She’s spent twenty-plus years building a tent, rental, and event company from nothing, and the passion still shows in everything she does. The business runs year-round, though the bulk of it happens across three busy seasons. About a year ago, she built out a real leadership team for the first time – four people around the table instead of just her. On paper, and honestly on most of the numbers too, it’s working. Heading into one of their peak seasons this year, they lost a huge wedding that was going to make their year and give them a ton of press. They fought hard and booked about 80% of that lost revenue. Rather than scaling down through the slower stretch of the calendar, she keeps her leadership team fully staffed year-round anyway – a real investment in keeping good people close.
By any reasonable measure, this is a team having a strong year. And I want to be clear about something before I say anything else: what they’ve built in twelve months is genuinely impressive. A year ago, this leadership team didn’t exist. It was all in the owner’s head – her vision, her instincts, her drive, with no structure underneath it yet. To go from that to four people around a table, real accountability starting to take shape, and a business that clawed back a major loss instead of folding under it, is real, hard-won progress. That context matters, because it makes what I noticed in that room even more worth paying attention to.
But sitting in that room, what struck me wasn’t the numbers. It was the trust – or more precisely, how unevenly it was distributed around that table.
Two of her four leaders are clearly, visibly loyal. One is her operations manager, a steady presence who runs setup and logistics and is fully behind her, no question. The other is a woman on the team who feeds off her drive, and it shows in how she shows up. The remaining two tell a different, more complicated story. One of them has been genuinely excellent – full of ideas, comfortable pushing back in the room, exactly the kind of voice a growing business needs. Lately, she’s started dabbling in catering on the side, a natural enough offshoot of the event business, but her energy in meetings has noticeably cooled. She recently asked to see the company’s balance sheet. The owner isn’t sure what to make of any of it. Is she pulling away, building something of her own? Or is asking to see the financials actually a sign she’s thinking like an owner, not less invested but more? She genuinely doesn’t know, and in the absence of an answer, her trust has quietly started to erode.
The fourth is a different kind of puzzle. She handles interior design for the events – genuinely gifted at creating beautiful, efficient spaces inside a tent that has to work as hard as it looks good. She’s dependable enough, content to be told what to do. She doesn’t push, doesn’t drive improvement, doesn’t really seem to enjoy leading people at all – she’d rather work alone. She’s clearly inspired by the owner.
Here’s what I keep coming back to: this is a leadership team getting real results while running on roughly half a tank of trust. Two members fully in. Two members somewhere between uncertain and quietly checked out. And I don’t think this business is unusual at all – I think a lot of leadership teams out there look exactly like this, and most owners haven’t stopped long enough to notice.
There’s a reason this matters more than it might seem to on the surface. Trust isn’t one item on a long list of leadership-team qualities. It’s the foundation everything else sits on. When trust is missing or uneven, people stop bringing real disagreement into the room, because disagreement feels riskier than staying quiet. Commitment gets softer, because nobody wants to fully commit to a decision they’re privately unsure the team actually believes in. Accountability gets awkward, because holding someone accountable requires a baseline of trust that isn’t fully there. None of this shows up right away in the numbers. It shows up later, as stalled growth that’s hard to explain, because the systems all look fine from the outside.
And left alone, it doesn’t resolve itself. It festers. The uncertain leader senses the owner’s hesitation and pulls back further, which deepens the very distrust that started it – a cycle that feeds itself quietly, for months, until an annual meeting rolls around and it finally gets addressed, if it gets addressed at all.
If you’re looking at your own leadership team and sensing a similar imbalance, here’s where I’d start, and I wouldn’t wait for the next scheduled review to do it:
1. Say what you’re noticing, directly and soon. Not a vague sense that “something’s off” – the specific thing you’ve observed, said plainly, in a real conversation. Silence is where distrust grows roots.
2. Ask before you assume. When something reads as a red flag – a request to see the financials, a new pursuit outside the business – ask directly what’s behind it instead of writing the story yourself. Often what looks like pulling away is actually someone reaching for more ownership, not less.
3. Build trust on purpose, not by accident. Create real space in your leadership meetings for honest conversation, not just metrics and scorecards. Share your own uncertainty out loud, and it becomes safer for others to share theirs.
4. Revisit the seat, not just the person. If someone genuinely prefers working alone and has no interest in leading others, that’s worth naming honestly – the seat might not fit, no matter how skilled or loyal the person is.
The businesses that keep growing aren’t the ones with zero tension on the leadership team. They’re the ones where the tension gets said out loud, early, instead of quietly running the team on half a tank.
And here’s the part that really stays with me: they achieved all of this – the recovery, the growth, the real progress – with trust running at maybe half strength across the team. Imagine what becomes possible once everyone at that table is genuinely on the same page. That’s not a small upside. That’s the difference between a good year and the kind of year that changes what the business can become.
If you’re sensing something similar with your own leadership team, I’d be glad to talk through it.