Are You Training Your Team or Avoiding a Conversation?

Have you ever paid for development programming designed to deliver a message to a specific person, yet involve the whole team? You might be engaging in Trojan Horse Training.

Do one person’s development needs result in an entire team initiative? That’s The Dilution Effect.

Are you designing programs that, at their core, serve as an organizational avoidance strategy for difficult decisions? That’s The Workshop Workaround.

Here’s a pattern I see over and over again in my work as a strategic HR consultant and executive coach.

A leader calls me in. They want help with professional development. The team needs to be “more collaborative.” Communication issues are causing things to “fall through the cracks.” People aren’t “innovative enough.” The ask is usually a workshop, a training series, or a performance framework — something that gives the whole team a common language and shared expectations of what excellence and performance look like.

Sounds reasonable. And it is. Until you start scoping the project.

Because what I almost always discover — within the first few conversations — is that the performance gap isn’t a team problem. It’s a one- or two-person problem. There are specific individuals whose behavior, communication style, or resistance to change is ricocheting through the entire group. Everyone else is working around them. And the leader knows exactly who they are.

The Strategy Behind the Training

Now, I want to be fair to the leaders who do this. Most of them aren’t avoiding the issue out of weakness or ignorance. They’re making a calculated choice. The training is a Trojan horse — a deliberate strategy with two hoped-for outcomes:

First, maybe the person will absorb the message. If the whole team hears it together, maybe they’ll recognize themselves in it. Maybe it lands differently when it’s framed as a shared standard rather than individual criticism.

Second, even if the individual doesn’t change, the rest of the team now has a common vocabulary. They have frameworks. They have permission to name the behavior. The hope is that peer accountability will do the work the leader is not able to do directly.

It’s a thoughtful strategy. I respect the intent behind it. Sometimes, the cost of the hard conversation is not worth the heat the leader will take. But there are real reasons it rarely works the way leaders hope.

Why the Indirect Approach Falls Short

The rest of the team already knows. They know who the training is really for. They’ve been navigating around this person for months or years. When they sit in a workshop on “collaborative communication,” and the person next to them is the reason everyone learned to work around the issue, the training doesn’t feel developmental. It feels like theater. I know it because of the palpable resignation of ‘I have so much work to do, and I have to be here, now?’

Meanwhile, the individuals who most need to hear the message are often the least likely to absorb it in a group setting. Long-tenured employees with deep institutional knowledge frequently have a strong self-concept tied to their expertise and their history with the organization. A workshop on communication isn’t going to crack that open. If anything, they may sit in the room thinking, “This is exactly what everyone else needs to hear.”

And then there’s the cost — not just in dollars, but in credibility. Every time an organization rolls out a team-wide initiative to address what everyone knows is an individual problem, it erodes trust in development programs. High performers start to wonder: Is this a real investment in my growth, or is this about managing someone else?

What’s Really Going On

Let’s name the deeper dynamic. The individuals at the center of this pattern are often people the organization feels it cannot confront directly. Sometimes it’s because they hold critical institutional knowledge that feels irreplaceable. Sometimes it’s tenure — they’ve been there so long that the leader feels a genuine sense of loyalty or obligation. Sometimes there’s an unspoken awareness that this person, at their age and career stage, would struggle to find comparable work and income elsewhere.

These are real, human considerations. Leaders who weigh them aren’t cowards — they’re compassionate. But compassion without candor isn’t kindness. It’s a slow erosion of standards, team morale, and ultimately, the individual’s own dignity. Because that person deserves the respect of being told the truth about what’s expected of them — and given a genuine chance to meet it.

What I Tell Leaders

When I identify this pattern in a scoping conversation, I say something that usually lands:

"You are about to spend tens of thousands of dollars to address a one- or two-person issue."

That gets attention. Not because training never has value — it often does. But because it reframes the investment for what it actually is: an expensive workaround.

From there, I ask the leader a simple question: Does the rest of your team actually need this development, or is this really about one or two people?

If the honest answer is that the team would genuinely benefit from shared frameworks and a common language — great. Invest in that. But don't expect it to fix the individual problem. Pair it with a direct conversation and an individual coaching engagement for the person at the center of the issue.

If the honest answer is that this training exists because of one or two people? Then skip the team-wide program altogether. A targeted coaching engagement — paired with clear, behavioral feedback from their leader — costs a fraction of the price and is the only approach that actually addresses the root cause.

Either way, the conversation the leader hasn't had is the conversation that matters most.

The Real Question

If you’re a leader reading this and feeling a flicker of recognition, ask yourself:

Am I designing this program for my team’s growth — or around someone I haven’t been willing to talk to directly about what isn’t working, what better looks like, and holding them accountable?

The answer doesn’t make you a bad leader. It makes you a human one. But the next step separates the leaders who build high-performing teams from the ones who keep designing programs around problems they already know how to name.

The most expensive training in the world is the one that replaces a conversation that was never had.

I’m curious: What’s the most expensive workaround you’ve seen an organization build around a conversation it wasn’t willing to have?