The Good Measure: Leadership

The Gap No One Trains Leaders For

Why capable people fail the moment leadership becomes human

There’s a gap in leadership that I don’t think we talk about enough—and honestly, I don’t think we train for it at all.

You see it everywhere once you start paying attention.

People who are smart, capable, experienced—people who know their job cold—struggle the moment leadership becomes about other people. Not the work. Not the metrics. The people.

And it’s not because they’re lazy or don’t care or aren’t trying.

It’s because no one ever really showed them how to do that part.


If I look back across the different organizations I’ve worked in, big ones, small ones, multi-billion-dollar companies, the pattern is pretty consistent.

We don’t actually train leaders how to coach and develop people.

What we do instead is… hope.

We hope someone is naturally good with people.
We hope they’ve picked it up along the way.
We hope a training or a course or a leadership seminar somehow sticks.

But it’s inconsistent. It’s random. It depends entirely on the individual.

Some leaders are good at it because they’ve developed that instinct or they care enough to work at it. Others aren’t—and there’s no real system catching that.

Even when there are internal courses or development programs, they’re often passive. People sit through them, maybe participate, maybe not, and then go right back to their roles. There’s very little accountability around whether anyone can actually demonstrate what they were supposed to learn.

No one slows the room down and says, “Show me. Do it again. Let’s work through this until it’s right.”

So we end up with leaders who have been “trained,” technically, but not developed in any real, behavioral way.

And then we act surprised when things break down.


I’ve seen this play out in very real, very human situations.

One example that stuck with me—there was a woman on a team who was objectively strong at her job. Detailed, capable, trusted with complex work. When the top analyst went on leave, she was the one they handed the most difficult desk to.

At the same time, in her review, her bonus was reduced. The reasoning? She didn’t “fight enough” in meetings. She was seen as too passive, not as competent.

So on one hand, she’s trusted with the hardest work on the team. On the other hand, she’s being told she’s not strong enough.

That’s not a performance issue. That’s a leadership issue—an inability to understand, communicate, and develop the person in front of you.


Another one.

A team leader—steady, reliable, high-performing. The kind of person who doesn’t complain, who carries weight, who helps others succeed. When a new manager came in, he supported him, coached him, helped position him well with the team.

A year later, he asked his director a simple question: when opportunities come up, am I being considered?

And the response he got was, “No one’s laying awake at night thinking about your future.”

That’s not just blunt. That’s careless. And it tells you everything about how that leader viewed people.

He left almost immediately.


And then there are the moments where pressure hits and you see people change in real time.

I had a situation where I’d been working for weeks to get information from another department. Emails, meetings, hallway conversations—every reasonable step you’d take. I had already decided that the next move was to involve my boss because I wasn’t getting traction.

Before I could do that, the other director went to my boss and framed it as if I hadn’t done my job.

I walked in Monday morning to an email listing all the ways I had failed and what I should have done.

The problem was—I had already done all of it.

So I responded, point by point, just explaining the steps I had taken. Not defensive, just factual.

That was interpreted as insubordination.

I got pulled into an office and chewed out for fifteen straight minutes.

Not because I was wrong. Because someone felt challenged.


That’s the gap.


Most organizations think the issue is skills.

Communication training. Tools. Executive presence. Confidence.

So they build programs around those things. They hire based on titles, on past companies, on perceived pedigree.

“This person was a VP at a billion-dollar company, so they must be a strong leader.”

But that doesn’t tell you anything about how they treat people.

And it definitely doesn’t tell you how they’re going to behave when they’re under pressure.


The uncomfortable truth is this:

We don’t have a leadership skills problem.

We have a human development problem.

Most of us were never taught how to communicate well in the first place. We learned by watching—parents, teachers, environments that were all dealing with their own pressures, their own insecurities, their own limitations.

Then we grow up, we get good at a job, and we get promoted.

Now we’re responsible for people.

But we’re still carrying the same patterns.


So what happens when things get tense?

We don’t rise to the occasion. We fall back to whatever our baseline is.

And for most people, that baseline isn’t built for leadership.

Stress starts to feel like conflict.
Giving direction feels confrontational.
Disagreement feels personal.

And people react.

They get defensive.
They get short.
They micromanage.
They withdraw.
They push harder than they should.

It’s not calculated. It’s not intentional.

It’s protection.


I’ve seen this play out in my own life too, not just at work.

People I respect, people I know have good hearts, make decisions in moments of fear that don’t line up with who they actually are.

Scarcity hits. Pressure hits. Something feels uncertain—and they go into self-preservation mode.

It’s not organized. It’s not thoughtful. And a lot of times, it creates more problems than it solves.

That doesn’t make them bad people.

It just means they weren’t prepared for that moment.


If I had to simplify it, the gap looks like this:

We don’t have a shortage of people.

We have a shortage of people who know how to develop people.

And that’s largely because they were never developed that way themselves.


So here’s a real question for anyone in a leadership role:

When things get difficult, when pressure is on, when something isn’t going the way you expected—

Do you protect your people?

Or do you push that pressure down onto them to cover your own uncertainty?


I’ve spent a lot of time thinking about this.

Partly because I’ve been on the receiving end of it. Partly because I’ve seen it happen over and over again. And partly because I’ve had to check it in myself.

There’s more going on here than just “better communication” or “stronger leadership presence.”

There’s a different way to approach this. A more intentional way to understand what’s actually happening in those moments and how to move through them without defaulting to the same patterns.

This is just a starting point—but it’s something I’ve been working through in a much deeper way.

More on that soon.


If this hits close to home, you’re not the only one seeing it.