The Self-Aware Leader
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Why Your Coaching Conversations Keep Going Nowhere
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Why Your Coaching Conversations Keep Going Nowhere

You've had the conversation three times. They said they'd work on it. Nothing changed.

You’ve had the conversation. Probably three times.

You told them they need to step up. Take more ownership. Be more accountable. They nodded, said they’d work on it, and walked out. Then the month closed and the number was the same number.

So now you’re at the fork. Either they don’t want it — which makes this a character problem and eventually a termination — or you’re doing something wrong. And there’s no third door you can see from here.

There’s a third door.

Here’s what happened in that conversation. You named a character trait. They heard “you’re a disappointment.” They agreed so it would end. And both of you left the room feeling like something got handled.

Nothing got handled. You handed them a mood, and a mood isn’t fixable. Nobody drives home and practices being more accountable.

The thing you actually have is a location problem.

Whatever your team does, it’s a sequence. Four or five steps between somebody starting a piece of work and finishing it well. Sales has a version. Support has a version. Every job has a version. And when someone is underperforming, it is almost never all five steps. It’s one.

I worked through this with a manager named Dana. Seven people, two years in the chair, promoted because she was excellent at the work itself. Her problem person — we’ll call him Kevin — was eight months behind and she’d run out of ways to say it.

Took us fifteen minutes to break Kevin’s work into steps. And Kevin was doing more first-touch volume than anybody on the team. Effort was not the issue. Where he was dying was the ask: the moment he had to get a person to commit to something. He’d get to that point and start explaining. More detail, more options, more reassurance. The other person would say “let me think about it,” and Kevin would say “of course, take your time.”

Every single time.

That’s one skill. He’d been going around that same corner for eight months and nobody had ever named it, because everybody was busy telling him to want it more.

And here’s the part I keep coming back to. Kevin didn’t know either. He knew he was behind. He didn’t know where.

Six reasons people underperform. Only one is about character.

Underperformance looks identical on the surface no matter what’s causing it. Same missed number, same quiet in the meeting, same look on their face. Underneath, it’s one of these:

  • Clarity — they don’t know what the standard actually is

  • Skill — they know exactly what to do and can’t do it yet

  • System — the company is in their way

  • Confidence — they can do it and won’t risk it

  • Consequence — nothing happens either way, so why change

  • Will — they’ve decided not to

Only the last one is a character issue. It’s also the rarest one on the list, by a lot. Most of what gets called lazy is a clarity problem or a system problem wearing a lazy costume.

I’ve gotten this wrong. I’ve written somebody off in my head, decided who they were, and found out months later I had never actually told them where the bar was. That’s not a them problem.

The episode goes deeper into the mechanics — the four questions that do more work than any advice you’ve got, why coaching six things at once fixes zero of them, and the twenty-minutes-a-week rhythm that makes it survivable when you’ve got ten people.


IN THIS EPISODE

  • (1:15) Why coaching to the final number is coaching a corpse

  • (3:30) Dana and Kevin — the manager who “handled it” three times

  • (7:00) The six causes of underperformance

  • (9:15) Ask first, tell second — the four questions

  • (10:30) One skill, thirty days

  • (11:15) Practice off the customer: role-play done small

  • (12:00) The weekly, monthly, and daily rhythm

  • (13:00) Somebody has to coach the coaches


THE MONDAY MORNING TEST

Three questions. Answering them honestly is harder than it looks.

  1. Name your weakest performer’s actual gap — the specific step where their work breaks. Not “they need to step up.” If you can’t name it, you don’t have a coaching problem. You have a visibility problem, and that’s a different fix.

  2. What did you ask someone last week that you didn’t already know the answer to?

  3. Pick anyone on your team. Can they tell you the one thing they’re working on this month? Go ask them.

That last one — their answer is your grade, not theirs.


The Self Aware Leader is a reader-supported publication. If this was useful, the best thing you can do is forward it to the manager who needs it.

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