Leadership circles can seem like highly functional, supremely competent teams, where the trains run on time and everyone is just smarter. That is true (in the best of cases), but not because there’s a magic line you cross when you officially enter the room. I’ve advised countless people against this fiction. The idea is that the politics thin out, the org chart starts working the way it’s drawn, and the people at the top operate with a clarity you haven’t been granted yet.
But I’ve now spent the better part of three decades in the rooms where things were supposed to have become clear — board sessions, executive offsites, the conversations that happen after the conversation — and I can report back: it is not clean up there. It is, if anything, messier. Not because the people are worse. Because the problems are different. Everything that could be resolved cleanly was resolved three floors down. What travels upward is precisely what refused to be.
I once told a client, during a particularly rough quarter, to stop thinking of his job as chess and start considering it 3-D chess. Same game but on multiple boards at once — which kind of makes it no longer the same game. Most people spend their careers on one board, one play at a time. If we’re very good, we begin to see two or three plays ahead, even five. But the strategy is always tied to one game, one history, one set of conditions.
At the C-suite and board level, it’s three boards or ten boards. It’s not infinite boards — that’s chaos, not leadership — but it is definitely not one single, contained game. What might start as ‘solely’ a pricing decision is also an investor story, and a board of directors’ conversation. Next it morphs into a signal to the broader executive team about whose responsibility it is, and that turns into a succession question. Nothing moves on just one board. They learn to watch multiple pieces shift in real time across everything else. The messiness doesn’t shrink as you rise; it gains dimensions.
The appearance is different. I had a colleague wistfully reminiscing aloud about the easier days ten years ago. I reminded him it wasn’t easy. Even in real time, the messiness at the top is often well-masked. Disagreements and compromises happen behind closed doors, and the rest of the organisation sees a united front. That isn’t necessarily a bad thing, by the way. It doesn’t even mean the negotiations in the room are dysfunctional. What it does mean is that you have to build a skill set — several, probably — that helps you thrive in that environment. You can’t collapse the boards; you’re going to have to learn to win three games at once. That can be incredibly disillusioning when you first enter the room.
But that’s not unusual. It’s a bit like professional American football players when they first get drafted — the best of the best at every university join a professional team. That’s moving into the top level. The problem is, everyone there is the best of the best. Everyone there came in knowing how to play with their team, in their division, to win their conference. They knew those stadiums, that seasonal shift. Now they’re learning new strategies, new teammates, new venues, new schedules. They got into the room because they excelled at a single version of the game. To thrive, they’ll have to survive season after season of new schedules, new players, sometimes even new coaches and management. That’s not chaos. That’s the game, at the top of the game.
Leadership teams don’t have tidier rooms. They just have better custodians.
So if you’re aspiring to the room, aspire accurately. Those who do best at the top aren’t necessarily the fastest or the smartest or the most ambitious. That isn’t to say that doesn’t help. But it mostly helps you get there. That’s the draft. The skills that make you thrive are those that let you abandon the idea of getting to a calmer, quieter norm. The norm is complexity, and friction, and uncertainty, and mutually respectful disagreement. It’s the messiness inherent in large-scale operations with global teams in the 21st century, on a 24-hour news cycle, in a nascent stage of the AI era. Winning is defined by the final score, not a breakdown of every play on the way to victory.
