Insights
Why your leadership team can’t be your sounding board
Your team can be excellent and this gap still exists. It’s not about their ability, it’s about their stake.
Leo Judkins, Founder, The iGaming Leader · September 2026
Here’s an assumption worth challenging directly: "I’ve built a strong team, they’re direct with me, so I’m covered."
You might have built exactly that team. Genuinely direct people who aren’t afraid to disagree with you in a meeting. That’s not the problem this article is about. The problem is structural, and it exists no matter how good your team is, no matter how safe you’ve tried to make it for them to speak up.
Everyone who works for you has a stake in what they tell you
Every person on your leadership team is thinking about more than the decision in front of them when they talk to you. They’re thinking about their compensation. Their career progression. Their title. What’s riding on this for their family. That’s not a character flaw. That’s just what it means to have a career that depends, in part, on what you think of them.
So they can be direct. Genuinely, comfortably direct, on plenty of things. But there’s a ceiling. Nobody wants to be the person who pushed hard for the decision that went wrong. Back a risky call, even one you’re personally confident in, and if it fails, you’re the one who’s tarnished. Your judgement gets questioned for years after. So the incentive, for almost everyone in that room, points towards safety. Towards the option that’s defensible if it goes wrong, rather than the one with outsized returns if it goes right.
That’s not mediocrity because your people are mediocre. That’s mediocrity because the structure rewards it, for them and, if you’re honest, often for you too.
And it runs both ways. There are things you don’t say to them either, for exactly the same reasons. Which means the honesty gap isn’t a failure on either side. It’s baked into the relationship itself.
What they’ll tell you, and what they never will
At a senior level, most good people will tell you when they think you’re wrong. That part usually works. What doesn’t happen, no matter how strong the team, is this:
They won’t tell you about a peer at their own level who’s underperforming. That’s not their story to tell, and it’s too risky to be the one who told it.
They won’t tell you they’re out of their depth. Saying that out loud has consequences. Staying quiet doesn’t, at least not immediately.
They won’t tell you about the decision that’s sitting, half-formed, in their own head. Because the moment they say it out loud to you, it becomes something that has to be actioned. Keeping it unsaid keeps it optional.
And they definitely won’t tell you they’ve been quietly looking elsewhere.
Underneath all of that sits a bigger issue. Everyone inside your business, however senior, however sharp, is looking at every problem through the same lens: your business, your history, your constraints, your way of doing things. There’s no genuine outside perspective in that room. Just the same set of assumptions, recycled, meeting after meeting, hoping that doing the same thing again produces a different result this time.
It doesn’t stop at the top either
I’ll say this plainly: it’s exactly the same for me. When people around me offer advice, there’s always a bias baked into it, even when they don’t realise it themselves. Even a question carries judgement in it. What I actually need, when I’m working through a real decision, is someone who’s built the same kind of business, hit the same kind of wall, and can tell me honestly what happened when they got it wrong.
I don’t have many people like that around me either. Mostly because I don’t know many people running the exact same kind of business I am. Which is, if I’m honest, probably the network I should be building for myself, not just the one I’ve built for everyone else.
That’s not a flaw in the argument. It’s the proof of it. If it’s true for me, running a business built entirely around solving this problem for other people, it’s true for you too.
Where this actually gets solved
Not with a better team. Your team can be excellent and this gap still exists, because it’s not about their ability, it’s about their stake in the outcome. It gets solved with people who have no stake in your business at all, who’ve made calls like yours before, and who’ll tell you what actually happened, including the parts that don’t make them look good.
See how the Inner Circles workQuestions this usually raises
If my team is genuinely direct with me, doesn’t that solve this?
Directness solves part of it, disagreeing on strategy or execution. It doesn’t solve the deeper part, because career stakes still shape what gets said, however direct the culture. Nobody wants to be remembered as the person who backed the call that went wrong.
Isn’t this just an argument for hiring better people?
No. Better people are still subject to the same incentives. A brilliant COO still has a career, a mortgage, a reputation, and the same reasons everyone else has for staying safe when a decision gets risky.
Can an executive coach fill this gap instead?
Partially. A coach can help clarify your thinking, but they haven’t usually built and run the exact kind of business you have, at this scale, in this industry. What you’re missing isn’t a better question, it’s someone who’s lived the answer.
Why does the writer admit he has this problem too?
Because pretending otherwise would undercut the whole point. The gap is structural, not a personal failing, and it applies at every level, including the person telling you about it.
Keep reading
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