The Nicest Manager in the Room (And Why That's a Problem)

A few years ago, I was working with a manager who was genuinely one of the nicest people I had ever met. Warm, well-intentioned, the kind of person who remembers your kid’s name and asks how your weekend was. Everyone liked them. Nobody wanted to disappoint them.

And things on their team were a mess.

Not dramatically. Not a fire. Just slowly, steadily getting worse. Instructions were vague. Accountability wasn't happening. Hard conversations kept getting pushed. The team was frustrated, not at the manager (because you couldn't really be mad at them), but at each other, at the situation, at the feeling that nothing was ever going to change.

From the outside looking in, I could see it. So I said something.

We sat down, I named what I was seeing, and I told them directly that their team needed more clarity and follow-through from them. They looked at me with wide eyes and said they understood. We talked through what needed to change. What that looked like. We actually practiced it. Wrote out what they would say, how they would say it, what to do if the conversation got uncomfortable or people got defensive. 

They went back to work, and did none of it.

It wasn't intentional. They just got into the room with a real person and froze. The script disappeared. The practiced words disappeared. What was left was the version of them that had always shown up, the one that would rather perpetually let something go than risk upsetting someone they genuinely cared about.

Eventually one of their best people left. When I found out why, it was hard to hear. She didn't leave because of the manager. She left because she felt like the team had just quietly re-organized itself around avoiding one person's potential discomfort. Like poor performance or what wasn’t working was something everyone had just agreed not to talk about. She felt invisible, and she was done waiting for that to change.

She wasn't wrong.

What that situation made clear to me is that telling someone they need to lead differently, and even practicing it with them, is not enough. The gap between knowing what to do and actually doing it when you're standing in front of a real person who might cry, or get defensive, or look hurt, is enormous. And for managers who have built their whole identity around being the one everyone likes, the gap doesn't close from one conversation.

It takes intention, commitment, and practice with other people. It takes hearing someone else in the room say "I freeze, too" and realizing you're not the only one. It takes letting go of shame, trying something, going back to work, seeing what happens, and having somewhere to come back to and work through it again.

That's what we built Turning Managers into People Leaders around. Three in-person days, spaced out intentionally, because one workshop where people take notes and head back to the office doesn't change much. The space between is the point.

DATES: April 24 | May 8 | May 22
WHERE: KWENCH, 2031 Store Street, Victoria, BC
COST: $1,000 per person. Retainer clients, reach out for your discount.

If you have a manager who knows what they should be doing and keeps not doing it when it counts, this is the right room for them. And if you're reading this and recognizing yourself a little, it's especially for you.

Register here: reimaginework.ca/learning/turning-managers-into-people-leaders