The Question Nobody Answers Anymore
- Nicholas Alexander
- Jul 28
- 5 min read
Every leader once had someone who would tell them they were wrong. Most lose that voice on the way up, and never notice it going.
A few years ago I placed a chief executive into a consumer business everyone expected him to turn around. He did.
Three years in, the numbers were good, the board was content, and he called me for what I assumed would be a catch-up.
Halfway through, he said something I have not forgotten.
The last genuinely candid conversation he could remember, the last time anyone had looked at him and said "I think you are wrong about this," had been with a former colleague at a different company, over a coffee that had nothing to do with his business.
Not his chair. Not his executive team. Not anyone who reported to him or answered to him.
He was not complaining. He was noticing.
And what he had noticed was that somewhere on the climb, one question had gone quiet.
The one every good leader leans on and most stop hearing answered: are you sure?
The voice that disappears
Early in a career, everyone tells you when you are wrong.
A manager corrects you. Peers argue with you in the corridor.
A mentor takes you aside and says the thing nobody else will.
You are surrounded by people who are structurally free to disagree, because disagreeing with you costs them nothing.
Then you rise. One by one, those voices are reassigned.
The peers become reports. The mentor retires or moves on.
The people who once argued with you now work for you, and the calculation changes for every one of them.
Telling the boss they are wrong stops being a free act. It carries a cost, real or imagined, to a career, a bonus, a relationship.
Most people decide it is not worth paying, and who could blame them.
So the challenge does not vanish with a bang. It erodes.
The meetings still happen. The papers still circulate.
But the sentences that begin "have you considered you might be wrong here" get shorter, then softer, then stop arriving at all.
You are still asking the question. Fewer and fewer people are willing to answer it honestly.
What the research quietly confirms
This is not a flaw of character or a failure of humility. It is structural, and it is common.
A study by Stanford Graduate School of Business, conducted with The Miles Group, found that nearly two thirds of chief executives receive no leadership advice at all from anyone outside their own organisation.
The survey is over a decade old now, and I would treat the exact figure as indicative rather than current, but nothing I have seen across the table since suggests the pattern has moved.
And when it asked those same leaders whether they would value such counsel, almost every one of them said yes.
Read those two findings together. Most people at the very top have no independent voice in their ear, and almost all of them want one.
The appetite is there. The structure is not.
"But that is what the board is for"
It is the obvious objection, and it deserves an honest answer.
Surely a chief executive with a chair, a full board and a room of experienced non-executives is not short of challenge.
The board is built for governance, not counsel.
Its job is to hold the leader to account, approve the strategy, and, if it comes to it, replace them. That is a vital function.
It is also the reason the boardroom is the last place many leaders feel able to say "I am not sure I can do this."
The chair who signs off your appraisal cannot also be the person you confess your doubts to without consequence.
The relationship will not carry the weight.
So the leader performs certainty in the one room designed to test it.
The board sees the polished version. The doubts go home in the car.
The pattern I see across the table
In twenty-five years of placing senior leaders, I have watched this play out more times than I can count.
Some of the most capable people I know, running their businesses well, are the most isolated in exactly this way.
Not lonely in the obvious sense. Surrounded by people, in fact.
But without a single relationship in which they can think out loud, be wrong, and pay nothing for it.
The ones who last tend to fix this on purpose. They build the missing voice back into their working life deliberately.
A former peer. A small group of leaders from other businesses who meet with no minutes and no agenda.
Someone with no stake in the company and no reason to tell them anything other than the truth.
Not a coach exactly, not a therapist, not a non-executive with governance to protect. A peer who owes them nothing but honesty.
They do it because they have understood what the busy majority miss.
The higher you climb, the more you have to manufacture the challenge that once arrived for free.
Questions worth sitting with
If any of this lands, here are a few questions worth taking into a quiet moment rather than your next board meeting.
1. When did someone last tell you that you were wrong, and you knew they had nothing to lose by saying it?
2. Who, in your current circle, is genuinely free to disagree with you? Not who could. Who would.
3. If you wanted to admit a real doubt about a big decision, who would you call, and would that call cost you anything?
4. Are the people who challenge you inside your business, where challenge carries a price, or outside it, where it does not?
5. When did you last go looking for the voice that tells you no?
If the honest answers are thin, that is not a verdict on you. It is a description of the seat.
Almost everyone who sits in it ends up here, and the ones who thrive are the ones who noticed early and did something about it.
Closing thought
The most dangerous moment in leadership is not when you are being told you are wrong.
It is when you have stopped being told at all, and mistaken the silence for agreement.
The question does not lose its importance as you rise. It only gets harder to hear answered.
The leaders who keep asking it, and who build the relationships brave enough to answer, are the ones still making good decisions in the years when the decisions actually matter.
Ask it. Then make sure someone in your life is still free to answer.
Maarten Jonckers
Managing Director, Nicholas Alexander Executive Search
Maarten also facilitates peer-advisory boards for business owners through The Alternative Board.
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