Here is the uncomfortable version of how to get a leadership team out of its comfort zone: most executive teams are not avoiding the hard conversation. They’re having it, often well, often with real candour. The problem sits one layer down, in the beliefs nobody thought to bring to the table at all. If you’re a CEO, CHRO, CFO, COO or transformation lead planning the next offsite or strategy day, this is for you, because the risk to your team isn’t a bad debate. It’s a good one, held on the wrong premise.

This is one piece of why leadership offsites fail to change anything: most of what goes wrong after an offsite was decided long before the room went quiet. This piece is about one specific cause: the assumptions your team stopped testing.

My team debates openly, how can we still be in a comfort zone?

Because comfort at executive level was never about tone. It’s about which beliefs the team has quietly agreed are settled. A leadership team can argue hard about the plan and never once touch the premise underneath it, the belief about the channel, the customer, the cost structure, because nobody in the room experiences that belief as a belief any more. It has become a fact. And you don’t debate facts, you build on them.

That’s the trap. Vigorous disagreement about tactics can coexist, indefinitely, with total agreement about a foundation nobody has re-examined in years. The team feels sharp. The room feels honest. And the whole conversation is still happening entirely inside the comfort zone, because comfort was never about how loudly you argue. It’s about what you’ve stopped questioning.

It’s worth separating this from psychological safety, because the two get treated as the same fix and they’re not. Amy Edmondson’s work on psychological safety, most fully set out in The Fearless Organization, is about whether people feel able to say the uncomfortable thing without being punished for it. That matters enormously. But it solves a permission problem, not a perception problem. A team can have complete psychological safety and still never surface a stale assumption, because nobody has realised there’s anything to say. Safety opens the door. It doesn’t tell anyone which room to walk into.

How do I find the assumptions nobody is questioning?

You look for the beliefs that were true once and have simply never been re-dated. Every experienced leadership team accumulates these. They were correct when the team formed them, a channel that converted, a segment that paid, a price the market would bear, and they were never wrong exactly, they just stopped being checked. Nobody decided to stop checking. It happened the way most comfort happens: gradually, and then not at all.

This is where Execution Intelligence™ becomes the useful lens: the gap between what an organisation decides and what it actually does. An untested assumption isn’t a philosophical loose end. It’s an execution cost. Your team can run a strategy flawlessly, hit every milestone, execute against the plan with real discipline, and still lose, two years later, because the premise underneath the plan expired quietly somewhere in year one. From the outside it looks like a market shift caught you off guard. From the inside, it was always a comfort problem, just one that took two years to show its face.

Picture the version that plays out most often: a belief about a channel, a customer segment or a pricing floor that was correct when it was set, in market conditions that ended years ago. Somewhere around month two, the newest executive on the team asks about it, because they haven’t inherited the belief yet, only its conclusion. They’re told, reasonably and confidently, “we’ve looked at that.” And they never ask again. That’s not a cover-up. It’s how a genuinely settled question becomes furniture, something everyone walks around without seeing.

Notice the sleight of hand in “we’ve looked at that.” It answers a different question than the one being asked. The newest executive wanted to know whether the belief still holds. What they got was confirmation that it was examined once, at some point, by someone. Separate those two claims deliberately: we’ve looked at that is a historical fact. We’ve tested that recently is a current one. Most leadership teams have plenty of the first and almost none of the second, and they talk about both as if they were interchangeable.

Who should raise them, and when, without derailing the offsite?

Groupthink is a different failure mode: how agreement forms under social pressure, even when the thinking underneath is genuinely mixed. We’ve covered how to break groupthink in a leadership team separately, and it’s worth reading if premature agreement is your team’s pattern. This is the quieter version: healthy debate, sound premise, and nobody assigned to ask whether the premise is still sound.

Three practical moves fix that, without needing anyone to be the difficult one in the room.

• Date your assumptions. For the two or three beliefs the strategy actually rests on, write down when each was last true, and name specifically what would have to change for it to stop being true. If nobody can answer either question, you’ve found where the risk is sitting.
• Give the newest person the standing job. Not a one-off invitation to speak up, an actual, ongoing brief to ask the naive question about anything the team treats as settled. Newness is a genuine asset for a limited window, and most teams waste it by asking new executives to assimilate as fast as possible instead.
• Bring in a voice with no stake in the last five years. Someone who wasn’t in the room when the belief was formed has no investment in defending it, and no social cost to naming it out loud. That’s often the difference between a question getting raised at all.

The timing matters as much as the mechanism. This has to happen at the start of the offsite, before the agenda has produced a single decision, because once the group has made its first call of the day, reopening a foundational premise starts to look like reopening everything that followed it. Nobody wants to be the person who unravels the morning. The opening slot is the only one where questioning the premise doesn’t cost anyone anything. After that, it costs the whole room its momentum, and momentum is the thing offsites are least willing to spend.

Where AJ fits in the room

This is precisely the gap an outside voice is built for. AJ Kulatunga works with executive teams at the start of the offsite, not to run a workshop on openness, but to name the specific beliefs a team has stopped testing, using Execution Intelligence™ to connect that comfort directly to what it will cost in delivery, not just in discussion. If your team is genuinely good at debate and you still suspect the real risk is sitting underneath it, that’s the conversation worth having before the agenda starts, not after the numbers come in. See how this works as a keynote speaker for a leadership offsite, or talk to AJ about testing the assumptions your next offsite will run on.