Perfection has a way of sneaking into leadership—driving us to higher standards, sharper focus, and greater outcomes. But left unchecked, it can also trap us in endless striving, where worth feels tied to flawless performance and every imperfection looms large. Real leadership begins when we release the need to get it all right and turn instead toward what matters most.
“You have to decide who you’re going to disappoint.”
Years ago, Bob Anderson and I were talking—one of thousands of conversations we’ve had about the business—when he shared a story that stopped me in my tracks. At the time, I was tangled up in a situation that, no matter how hard I tried, wasn’t going to resolve neatly. I was caught in the trap of trying to make everything OK for everyone, to meet unreachable standards, and to hold it all together.
With just a handful of words, Bob reframed how I think about leadership, perfection, and the futility of trying to make everyone happy.
He told me about a lunch he’d had years earlier with his friend and mentor Peter Block. True to form, Peter skipped the small talk. “How old are you now?” he asked. “Fifty-five,” Bob replied. Without hesitation Peter said, “Ah, then you’re at the age where you have to decide who you’re going to disappoint.”
That line landed hard for Bob—and just as hard for me when he passed it on. Leadership often feels like an unrelenting pull toward perfection: pleasing everyone, meeting every demand, making no mistakes. But sooner or later we hit the truth—there’s no way to satisfy everyone and everything. In those moments, the question must shift from How do I get everything right? to What really matters most?
Peter pressed further: “Fifteen years from now, you’ll be 70. What do you want to do between now and then? And who will you have to disappoint in order to do it?”
That’s the pivot. That’s when perfectionism starts to loosen its grip—not because we stop caring, but because we start choosing. We choose what matters most. We choose where to put our energy. We choose to lead with intention, not obligation.
Perfect, as a dimension of the Leadership Circle Profile®, reflects our drive for high standards. That drive can fuel excellence—but when it becomes tied to self-worth, it runs us into overdrive. We end up exhausted, isolated, and frustrated with ourselves and others. The leadership move is not to abandon excellence but to hold it in balance: to choose consciously, to delegate, to release appearances, and perhaps most importantly, to disappoint.
So today I invite you to ask: What do you want to do with your time, your leadership, your life? And who might you need to disappoint to make that possible?
It’s not easy. But it is freeing. And it’s the beginning of a different kind of leadership—the kind rooted in purpose, not pressure.
Bill Adams, Co-Founder and CEO
Bill Adams loves people and is passionate about relationships, leadership, and business. He is a serial entrepreneur who has started, owned, and sold multiple businesses. As a founder and the current CEO of Leadership Circle, Bill brings 30 years of experience to his clients—the CEOs of major Fortune 500 corporations, nonprofits, and private equity startups. In addition, Bill co-authored Mastering Leadership and Scaling Leadership. As a trusted advisor, teacher, consultant, and coach, he works with CEOs and top teams in fulfilling the promise of leadership.
