A Sparring Partner for CEOs: What It Is and How to Find One

TL;DR: A sparring partner for a CEO is someone at your level who can follow your situation without a tutorial, challenge your thinking, and has nothing to gain from your answer. It is the most common thing leaders ask me for, usually in those words. Boards, investors, co-founders and partners all care about you, and all have a stake. A chatbot can structure your thinking but cannot sit with you in real uncertainty. A good sparring partner does both: pushes back hard, and stays with you while you work it out.

What leaders actually ask for

When new clients fill in my intake form, the word that comes up most is sparring. Some of the answers, word for word:

• "I have never received any sparring or coaching from another (x)CEO, who understands what I'm going through... I'm missing that sparring (a co-pilot), with whom I can liaise proactively and reactively, but also someone who can challenge me!"
• "Sparring, direction and time."
• "Right now I miss good colleagues that I can spar and discuss things with."
• "Planning to build a world-class start-up and feeling alone in my journey."

The first one came from a leader who had gone from director to CEO in five years. They loved the job. What they did not have was anyone to think with.

What a sparring partner is

In Danish business language, sparring means thinking out loud with someone who pushes back. In English people say sounding board or thinking partner. Neither quite catches it. A sounding board reflects. A sparring partner hits back, on purpose, so you get stronger.

A good sparring partner for a CEO has four qualities.

They have been in a similar seat. They can follow a board dynamic, a co-founder conflict or a down round without needing it explained.

They have no stake in your answer. No equity, no vote, no shared payroll, no dinner table.

They challenge you. Agreement is cheap. The value is in the question you did not want to be asked.

They stay. Sparring works over months. One good conversation helps. A relationship that knows your patterns helps far more.

Why CEOs end up without one

Most CEOs have plenty of people to talk to. That is the problem. Your board decides whether you keep your job. Your investors have a fund to return. Your co-founder carries the same weight you do. Your partner at home pays a price when things go badly. Every one of them cares about you, and none of them can hear "I don't know if I can do this" without something shifting.

The research backs this up. In The Whole Human Leader I cite the Harvard Business Review CEO Snapshot Survey: half of CEOs feel lonely in the role, and 61% say it hurts their performance. Only 12% of CEOs have a formal coach.

The more senior you become, the less likely you are to show doubt or ask for help. In the book I wrote about Priya, a strategy director in London who told me she had not said "I don't know" at work in three years. Her colleagues had stopped including her in discussions, because they assumed she already had the answers. Just when she needed other people's thinking most, she had cut herself off from it.

Why a chatbot is not a sparring partner

Many leaders now take their hardest questions to AI. I understand why. You can think through a strategic decision or rehearse a difficult conversation without revealing uncertainty to another person. On one level it works. AI can process information, offer frameworks and help structure your thinking. Those are useful.

What AI cannot do is what we in Denmark call fællesskab: a sense of shared responsibility and real fellowship. It cannot sit with you in genuine uncertainty and help you feel less alone. It cannot draw on having faced a similar moment itself. And it will rarely tell you the thing you least want to hear.

In my experience, leaders who use AI as a substitute for human sparring often end up more isolated, with better-structured thinking and the same blind spots.

Sparring partner, mentor, peer group or coach?

A mentor shares how they did it. Useful for knowledge gaps, limited because their company was not yours.

A peer group of other CEOs gives breadth and reassurance that you are not alone. It rarely goes deep on your specific situation, and some things are hard to say in a room of peers.

A coach works on your judgment and your patterns over time, with homework and follow-through.

A sparring partner is the function all three can provide when they are done well: someone at your level, with no stake, who challenges you and stays. In my practice, sparring is the core of the coaching. I built six companies over fifteen years, so I can follow your situation from the inside. I ask for radical transparency and I give constructive candour back.

How to find the right sparring partner

Check that they have carried real consequence. Someone who has made payroll, faced a board or lost a company understands pressure differently.

Make sure they gain nothing from your answer. If they hold equity or want your business for something else, their advice bends.

Test whether they will disagree with you. In the first conversation, notice whether they push back or just nod.

Agree on rhythm. Sparring works best on a fixed cadence, every two weeks for most CEOs, plus access for live decisions.

Common questions

What is a sparring partner in business?
Someone you think out loud with who actively challenges your reasoning. For a CEO, usually an experienced outsider at a similar level, with no stake in the outcome.

Is a sparring partner the same as a coach?
They overlap. A good coach for a CEO spars. Coaching adds structure: regular sessions, work between them, and accountability over months.

Can my board chair be my sparring partner?
Sometimes, for business questions. For questions about your own capacity, doubts or future, the chair's role makes full honesty hard.

How often should a CEO meet a sparring partner?
Every two weeks is a good rhythm for most. Weekly during a crisis or transition.

The short version

Every CEO needs one person at their level who can challenge them and has nothing to gain from the answer. If you do not have one, that is the gap to close first. This is the heart of my 1-on-1 executive coaching. More on the role in what a founder coach is.