There’s a moment most CEOs hit at least once a quarter. A decision that’s yours alone. You bring it to your leadership team — and you can feel them positioning before they even speak.
The CFO is thinking about cash. The Head of HR is thinking about morale. The board is thinking about quarterly performance. They want you to succeed, and they’re competent at their jobs. But every one of them lives inside the consequences of your call. None of them can be fully disinterested.
That’s why your most important advisors may not work for you at all.
“You need people you can bring your mess to,” Heather Stone says — people who will listen and help rather than criticize, people who won’t expect you to posture. “You can’t always get that from the inner circle team that you pay in your company.”
Who are these people? One of them might be in your bed. Studies have found a strong correlation between happy marriages and career satisfaction — not because spouses are tactical consultants, but because they see you whole. They know what you’re carrying. They tell you the truth when no one else will.
The rest of the list looks like this: a childhood friend who knew you before the title. A mentor two decades ahead of you. A peer running a business in an industry that has nothing to do with yours. Each one sees a different angle. Together, they make sure you don’t end up making the call alone.
Stone tells one story I keep returning to. In 2020, when her outdoor products company was bleeding out, the tip that saved her wasn’t an internal idea or a consulting deliverable. It came from someone in her outside circle — someone with no skin in the game except wanting her to come through it. That tip was a government funding lead. It kept the company alive.
That’s the real test. Not credentials. Not industry expertise. Disinterest plus genuine investment in your getting it right.
Build that circle deliberately. The people who love you aren’t always the people who will challenge you, and the people who will challenge you aren’t always the ones who will stand by you. The two lists usually need to overlap on purpose.
Some of the best advice you’ll ever get will come from people who have nothing to gain from your decision — except wanting you to get it right. Let’s talk.