A COACHING ROOM DISCOVERY
The first session with a senior leader rarely begins with the real subject.
They arrive with an agenda. A difficult board. A region that missed its number. A successor who is not quite ready. All of it is true, and all of it is surface. Somewhere around the third or fourth conversation, once the trust has settled, the real subject walks in and quietly takes a chair. After more than eighteen thousand hours in that room, I can tell you it is almost always one of three fears.
These are not the fears of weak people. They belong to your strongest. The top performer, the region head with the trophy cabinet, the CXO everyone assumes has it handled. If you lead critical talent, or you coach it, learn to recognize these three, because each one is running a part of your business while dressed up as ambition, independence or drive.
I HAVE ALWAYS WON. I CANNOT LOSE NOW.
Listen to the record first. Top of the batch. Best region head. Highest revenue, year after year. Then listen to what sits underneath it. A leader who has never lost does not experience a setback as a setback. He experiences it as the end of who he is.
So, slowly, he stops taking the risks that made him. He chooses the safe market, the predictable hire, the strategy he already knows he can deliver. From the outside it looks like discipline. Inside, it is a man guarding a record, and no company ever grew on a guarded record.
I do not argue with this fear. Argue with it and it digs in. Instead I ask:
“Who would you be if you lost this one?”
Then I wait. Usually a long time. Later:
“What has winning cost you that no scoreboard ever recorded?”
And when he is ready:
“If your record were guaranteed safe, what would you try next?”
That last question shows him the cage. Most leaders discover that the thing they most want to do and the thing they are most afraid to do are the same thing.
NO ONE WILL BE THERE WHEN I NEED THEM
The second fear sounds like strength. I am alone in this game. I have learned to do it myself. I do not need anyone.
Follow that belief into the organisation and you can see the invoice. He does not delegate. He trusts two people, perhaps one. Decisions queue outside his door. His brightest deputies stop bringing ideas, because they have learned he will redo the work anyway. Then he tells me, quite sincerely, that nobody steps up. He has built the very loneliness he set out to survive.
Reassurance is useless here. A capable leader can smell it from across the table. So I ask:
“When did you decide you had to do this alone?”
There is nearly always a moment. A partner who walked away. A boss who took the credit. A time he reached out and nobody reached back. Then:
“What does doing everything yourself protect you from?”
And finally:
“Who on your team has never been given the chance to prove you wrong about them?”
That one usually produces a name.
“None of it appears in a performance review. All of it appears in the business.”
ENOUGH IS A NUMBER THEY HAVE NEVER WRITTEN DOWN
The third fear is the oldest of the three and it is rarely about money, even when money is the language it speaks.
I hear versions of the same history. My father lost everything. My last company did not end well. I have seen what happens when you do not have enough. So, they push. More revenue, more territory, more security, more. Every target met becomes the floor for the next one. They cannot rest, because the past has taught them that the moment you rest is the moment it is taken away.
This leader is not greedy. He is frightened, and the fear is borrowed from a younger version of himself who stood and watched something collapse. My questions here are the gentlest of the three, because they go nearest the wound:
“Whose fear is this? Yours today, or the boy who watched it happen?”
“What number would be enough?”
Almost nobody has an answer. They have spent decades running towards a finish line they never drew. So I ask one more:
“If you already had enough, what would you do differently on Monday morning?”
The answer is usually the life they have been postponing.
WHY I NEVER TELL THEM THEY ARE WRONG
You will notice I did not tell the winner that failure is fine, or the lonely leader to trust more, or the anxious one that he has plenty. Advice like that bounces off a strong mind. He has heard it a hundred times, usually from people who have never carried what he carries.
A good question does what advice cannot. It lets the leader find the answer in his own voice, and a conclusion you reach yourself is one you will actually act on. That is the whole craft at the top. Less telling. Better asking. Far more silence than most people can bear.
A WORD TO THE CXO WHO LEADS CRITICAL TALENT
Look again at your best people. The one who never misses a number may be terrified of the first miss. The one who never asks for help may be the bottleneck nobody dares to name. The one who keeps raising the target may be running from something that happened thirty years before you ever met.
None of it appears in a performance review. All of it appears in the business.
You do not have to coach them yourself. But you can stop rewarding the fear as though it were character and give them one room safe enough to say it out loud.
It begins, as it always does, with the courage to ask the question we would rather not answer ourselves.
S. Neroshan Silva, MCC. Written from the coaching room, in Ratmalana.
