The One Skill That Multiplies Everything Else

The coaching conversation done right — and what it can change

At some point leadership stops being about what you can do — and starts being about what you can unlock in others.

It is 1982. I am a young program director for the YMCA of Houston, watching colleagues move up the ranks while I stay where I am.

Houston is growing fast — new suburbs, new YMCAs, new opportunities appearing almost monthly. Careers are accelerating around me and mine feels stalled. I am doing good work. I know I am. But good work and forward momentum are not always the same thing, and I am old enough to know the difference and young enough to find it infuriating.

So I do what any ambitious young leader does. I request a meeting with the COO.

Gary Nichols was the kind of leader people strained to hear. Not because he was loud — because what he said was worth the effort. Highly respected. Easily approached. The kind of presence in a room that made everyone in it sit up a little straighter without quite knowing why.

I walked into his office ready to make my case. He gestured to a small circular table in the corner — not his desk, not the chair across from his authority, but a round table. Equal sides. No head. A deliberate leveling of the ground between us.

I spoke about what I was seeing. Colleagues moving forward. My own sense of being left behind. I asked him directly: what did I need to do?

His answer was simple. And at the time, infuriating.

“Well, Jim — what do you want to do?”

That was it. No roadmap. No list of competencies to develop. No guidance on which opportunity to pursue or which relationship to cultivate. Just a question — clear, unhurried, and completely serious — that handed the whole thing back to me.

I wanted a handout. He gave me the power to choose for myself.

I didn’t understand it then. I left that office with the answer I’d been given turning over in my mind, not quite sure what to do with it. It took years — and the experience of supervising my own staff, watching my own direct reports wrestle with the same questions I had wrestled with — before I understood what Gary Nichols had actually done in that room.

He hadn’t withheld his wisdom. He had offered me something more valuable: the recognition that I already had mine.

———

That’s what coaching does at its best.

Not solve. Not direct. Not hand down the answer from a position of experience and authority — though there are moments, as I wrote in the last article, when that is exactly what’s called for.

Coaching, at its best, unlocks something in the person across from you that they couldn’t access on their own. It asks the question that makes them stop and actually think — not perform thinking, not search for the answer you want to hear, but genuinely reckon with what they know and what they want and what they’re willing to do about it.

One conversation, done well, can change the trajectory of someone’s career. I know this because one conversation changed mine. It just took me years to realize it had happened.

———

The coaching skill I teach isn’t complicated. But it is demanding.

It requires you to be more interested in the other person’s thinking than in demonstrating your own. More committed to their development than to the efficiency of just telling them what you know. More willing to sit with an uncomfortable silence — the silence that follows a good question — than to fill it with the answer that’s already forming in your mind.

It requires four things, in sequence:

First — explore. Before you offer anything, understand what the person actually wants from this conversation. Not what you assume they need. What they came for.

Second — plan. Together. Not you solving it for them, but both of you identifying what’s possible and what a meaningful next step looks like.

Third — act. Support without taking over. Accountability without control. The difference between checking up and checking in.

Fourth — sustain. Ask what continuing to grow looks like for them — not just in this conversation, but after it. Most coaching relationships end too soon. The sustaining question is what makes the learning stick.

Woven through all four: reflect. On what you’re noticing in them. On what’s happening in you. On whether your questions are driven by genuine curiosity or by your own agenda for where this conversation should go.

That last one is the hardest. And the most important.

———

Gary Nichols retired years after that conversation in his office. I found him and thanked him — for the question he asked, for the table he chose, for the patience he had with a young program director who wanted an answer and needed something else entirely.

He probably didn’t remember the conversation. That’s how it often goes with the best coaching moments — they are unremarkable to the coach and unforgettable to the person being coached.

That asymmetry is worth sitting with.

Every conversation you have with someone on your team is an opportunity to be Gary Nichols for them. To ask the question that hands them back their own power. To trust their thinking before they trust it themselves. To plant something that may take years to grow — and may never be traced back to you.

That’s not a small thing. That’s the whole thing.

The skill that multiplies everything else isn’t a technique. It’s a decision — made fresh in every conversation — to be more interested in what the person across from you can discover than in what you already know.

Make that decision consistently enough, and you stop being a manager who leads.

You become a leader who develops.

And the people around you will carry what you gave them long after they’ve forgotten the conversation it came from.

Who asked you the question that changed how you thought about your own path? I’d genuinely like to know — and I suspect the answer will tell you something important about the kind of leader you want to be.