You Can’t Retrain Your Way Out of a Leadership Problem

Too many leaders use training as a smokescreen for deeper issues. If your culture’s off, no workshop will fix it. Here's why training won't save you — and what actually might.

Steve Simpson

7/21/20252 min read

Years ago, I was speaking at a national conference for a real estate group. I arrived early to get a feel for the room and sat quietly in a planning session before my presentation.

As I listened, it became clear that “training” was being thrown around as the answer to almost every problem raised.
Struggling to meet targets? Training.
Internal tension? Training.
Poor follow-through? More training.

By the time I stood up to speak, I was convinced: training wasn’t just a solution. It had become code for “the problem is with the staff.”

And that’s a serious red flag.

Don’t get me wrong — I’ve worked with enough organisations to know that good training can make a real difference. But if the culture is off, no amount of content or classroom time is going to fix what’s really going on.

Here’s where UGRs come in.

Because the moment someone is sent to training, there’s a UGR lurking behind it. It might be:
“Around here, training is a punishment for underperformance.”
Or:
“Around here, the people who need training never get sent.”
Or worse:
“Around here, training doesn’t matter — nothing changes anyway.”

In the same session, I asked the group to consider this scenario:
A staff member attends a one-day training program. They come back to work… and no one says a word. No follow-up. No curiosity. No expectation that anything should shift.

That silence writes a UGR more powerfully than anything in the training handbook.

Here’s the deeper issue: when leaders see training as the fix-all, they’re often avoiding a harder truth — that the problem might not be skills. It might be clarity. Or leadership. Or a culture where people have stopped caring because their previous efforts went unnoticed or unrewarded.

And it’s easier to tick a box and send someone to training than to confront any of that.

If you want training to work — genuinely work — then the UGRs around it have to shift. That means training is positioned as a shared opportunity, not a personal shortcoming. It means everyone, including leaders, participate. And it means learning is seen as something to apply — not just attend.

Because if the only people going to training are those who are “not performing,” then don’t be surprised when it doesn’t stick.

Or worse — when it backfires.