You can’t undo years of bad leadership conditioning with a single declaration.
A new CEO I was working with was frustrated. He’d been telling his executive team for months that he wanted them to take more risks, be bolder, try new approaches. But they kept playing it safe—asking for permission, finding reasons NOT to try something, defaulting to caution.
“I’ve told them a hundred times I want risk-taking,” he said. “Why aren’t they listening?”
The answer wasn’t in what he was saying. It was in what the previous CEO had done.
Under the former leadership, “risk-taking” was exactly that—a risk to your career. The previous CEO talked about wanting bold moves, but the organizational lore ran deep. Whether it was true or just stories, the belief was that when leaders took risks and failed, they either got publicly dressed down in leadership meetings or quietly “mutually agreed” to part ways.
I explained it to him like this: It’s like working with a personal trainer who teaches you to deadlift with terrible form for years. Even when a new trainer shows up and demonstrates the correct technique, your body still wants to default to what it learned before. The muscle memory is deep.
His team had learned that empowerment speeches and risk-taking rhetoric were just words. Their survival instincts—built over years of conditioning—told them to keep their heads down and play it safe.
You can’t override that kind of organizational muscle memory with a single declaration. You rebuild it through behavior, through rewarding the attempt, not just the outcome. Through asking again and again and again, and positively reconizing (publicly!) when someone exhibits the behavior you want. Through proving—repeatedly—that this time, the ask is real.
What old leadership patterns are still running your team’s playbook? And what are you doing daily to help them build new muscle memory?
Looking to increase the cohesion, trust, and impact of your leadership team? Reach out and let’s discuss The Compass Team Experience and how I can help.








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