Four empty chairs
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‘I’m surrounded by people who mean well, but I can’t really talk to them.’
These were the words of a CEO I work with. She has a board that backs her, an executive team that respects her, investors who returned her calls on the same day and on paper she looked well supported.
I’ve heard a version of that sentence from nearly every CEO I’ve sat with.
We tend to file it under loneliness, as if it were a mood that floats through the office from time to time and it’s often followed by the same advice: get more exercise, find a mentor, join a peer group.
Some might think that reasonable. If you’re a CEO today or on track to become one soon, that advice is beside the point.
The isolation a CEO feels is not the absence of people. It’s the absence of a particular kind of person. And once you see why, it stops being a feeling you manage and becomes a gap you can fill.
Look at who typically surrounds a CEO
The board is accountable for the company’s performance and, often, holds the CEO’s role in their hands. Investors are watching and awaiting a return. The executive team reports to the CEO and has careers shaped by staying in favour. Every one of these people can be capable, loyal, and genuinely well-meaning. And every one of them has something to gain from your answer.
That’s the design flaw. The CEO (or country or regional leader) role assembles a set of advisors whose counsel is entangled with their incentives, and then leaves the CEO to notice, usually alone, that there is almost no one in the building with nothing to gain from what they decide.
The client I mentioned had inherited exactly this. When we started working together, the options she was weighing had been shaped by the pressure and emotion of the moment, and by a room full of people who each held a stake in which way she moved. She wasn’t short of advice. She was drowning in it.
What she was missing was someone disinterested.
Here’s the thing that frustrates CEOs when that becomes obvious. You would never leave a critical function in the business unstaffed and then describe the gap as a bad mood. You fill the role.
Yet when it comes to counsel, the most important input into the critical decisions you make, most CEOs run with half the chairs empty and tell themselves they’re simply feeling isolated.
Isolation is an org chart problem, and org chart problems have solutions.
Over the years I’ve come to think of it as a counsel map. Four seats every CEO needs filled, each doing a job the others can’t.
The Mirror reflects you back honestly. Not the version you present to the board, the one that’s actually there. The Mirror tells you when you’re avoiding a conversation, when your confidence is bravado, when the story you’re telling yourself about a situation has drifted from the facts. Most CEOs have people who flatter them and people who fear them. Few have someone who describes them accurately.
The Challenger interrogates your reasoning. Their job is to find the weakest assumption in your logic before the market does. And a good Challenger doesn’t disagree for sport. They pressure-test the decision you’re most attached to because you’re the least likely person to examine it yourself.
The Elder has survived what you’re facing. They’ve sat where you’re sitting, made the call you’re about to make, and lived with the consequences. The Elder can’t tell you what to do, but they can shorten the distance between your problem and someone who has already seen the implications of the decision.
The Peer carries the same weight right now. Another CEO in the thick of it, close enough to your reality that you don’t have to explain the stakes. The Peer is the one who can say “me too” and mean it, and that recognition provides a type of relief and understanding that no one else can.
Four seats
The Mirror, the Challenger, the Elder, and the Peer.
The status quo I see when CEOs map their own counsel is something like this. Two seats are filled by the same person, usually a trusted deputy or a spouse carrying more than their share, and two seats sit empty.
The Elder chair is often vacant because asking for help from someone who’s done it feels like admitting you can’t. The Peer chair is empty because the people who’d qualify are the same people you compete with, or the same people to whom you would feel uncomfortable declaring your uncertainty.
The CEO I mentioned earlier had leaned on her executive team for all four seats, which is an impossible ask. Your team can’t be your Mirror when their career depends on your approval. They can’t be your Peer when they don’t carry the final accountability. My job was never to replace anyone in her business. It was to sit in the chairs no one in her business could occupy: to ask the questions her team couldn’t ask her, to challenge the reasoning her board had a stake in, and, when the load was genuinely too heavy, to offer advice based on lived experience and help carry the load. Mostly it was to help her slow down and regain perspective or as she says, ‘separate the decision from the week it arrived in’.
She told me afterward that the options she started with had been shaped by pressure, and the decision she landed on was shaped by her values. That gap between the two is where counsel lives.
So, when you share with a CEO you know, let them know this: CEOs don’t need four more friends. They need four functions covered, and no single person holds more than one of them well.
Draw your own map this week. Four chairs. Write a name in each. Be honest about the ones where you’ve written the same name twice, and the ones where you’ve written no name at all.
Most CEOs discover they’ve been asking one or two people to sit in every chair, and calling the strain of that arrangement loneliness. Name it properly and it becomes something you can act on: a staffing gap, and you’ve held the authority to fill it all along.
Look at your four chairs. Which ones are empty, and who have you quietly been asking to sit in two at once?
PS If this essay helped, Episode 221: How CEOs lead when certainty disappears from my podcast is worth a listen. Tune in on Apple Podcasts, Spotify or wherever you get your podcasts.
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