Working with difficult people can be… well, difficult. In this illuminating post, Dean talks through his simple method for recognizing the core of the difficulty and neutralizing it without bruising anyone along the way.
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If you’ve ever worked with humans, you’ve worked with difficult ones. I see it constantly when coaching teams for high-stakes interviews and sales pitches. The difficult person usually shows up fast—they invalidate others, dominate conversations, or bring an aggressive tone that shuts the room down. When that happens, ideas stop flowing, and the team loses its sense of safety.
When I identify that person, I don’t confront them. I affirm them—not on the behavior, but on the valid point buried inside whatever they said. There’s always something useful in there, and I look for it intentionally. When I affirm them publicly, I show them I will represent them well. That softens their defensiveness and reduces the threat they feel.
At the same time, I watch for the person who just got shut down. When someone gets invalidated, I step in as their advocate: “Hang on—I want to reinforce what you just said,” and I lift their idea back up. This signals to the team that everyone’s contribution is safe and worth exploring.
Once the difficult person feels seen, I can redirect or challenge them without triggering more resistance. Even better, I can connect what’s strong in their idea to what’s strong in someone else’s. Teams don’t need one voice dominating—they need integration. My job is to weave the good pieces together so the group can move forward collectively.
Most “difficult people” are actually vulnerable people protecting themselves. If you affirm what’s right, protect those they shut down, and connect everyone’s contributions into a shared direction, you transform the dynamic. You make them easier—and you make the whole room better.
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