Some Environments Aren't Broken. They Just Weren't Built for People Like You.

One of the hardest conversations I have with leaders is this one: what if the problem isn't your execution? What if it's fit? I remember the moment this question crystallized for me in a recent session when a client — a senior leader at a small college — was describing two completely different professional worlds he inhabited simultaneously.

The thing about fit is we tend to experience its absence as personal failure long before we recognize it as a structural mismatch. There's a finding from a Harvard Business Review survey of 140 executive coaches that I keep coming back to. When researchers asked what makes a coaching engagement succeed, three ingredients rose to the top: the leader must be genuinely motivated to change, the chemistry between coach and leader must be right, and there must be real commitment from the organization to developing that person. Miss one, the experts warned, and don't bother — coaching can't fix a systemic issue beyond the individual’s control. I've come to believe those three ingredients describe far more than coaching. They describe sustainable leadership itself.

Fit — does this environment actually match how you work, what you value, and what you're good at?

Support — is the institution genuinely invested in your success, or merely in your output?

Agency — do you have real authority to act on what you see?

When all three are present, leadership is sustainable. When one is chronically missing, you can compensate for a while. When two are missing, you're not leading. You're surviving. Leaders who hold high standards in low-accountability cultures don't usually fail. But they burn. They spend enormous energy trying to move systems that have no interest in being moved.

Two stories from the coaching room

Consider another client of mine, a senior academic at a large institution. By every external measure, she was succeeding — the person who "does everything," the one colleagues introduce as indispensable. But indispensable, it turned out, meant something narrower: she had become everyone's administrative person, the default crisis manager at work and in her family, the keeper of details that were never hers to keep, and the work she was actually built for — vision, strategy, the long view — kept getting crowded out. When she finally named what the next year's workload would cost her health, the question on the table wasn't "How do I execute better?" It was "What is actually available to me here, and what isn't?" Support, in her environment, flowed in one direction, and her clarity about that wasn't defeat.

Then there's the leader I mentioned at the start. What struck me most in our session was his clarity about a critical hire his role depended on. He didn't hedge it. He didn't soften it with institutional language or apologies. He said, in effect: "This is what I need to execute my role, and if it doesn't happen, I'll leave,” which is not ultimatum-making but agency.

What institutions get wrong about this

Gary Daynes, in his book How to Be a Small College, makes an observation about institutions that echoes everything I see in individuals. "Culture eats strategy for breakfast," he notes, has become a boardroom truism — but he extends it: when culture eats strategy, operations set the table. Strategy rarely fails because people dislike it. It fails because the way work actually gets done quietly runs counter to it. Authority over policies sits with people who never implement them; processes here cancel policies there. Now read that as a description of a leader's environment rather than an institution's, and you have the anatomy of low fit. ‍ ‍

Daynes also argues that institutions should worry about fragility before efficiency — that resilience comes from connection, feedback loops, and participation rather than from running leaner, and I say the same is true of a career. ‍So I’m not here to talk about quitting. Let’s have a conversation about clear-eyed evaluation. What's actually available where you are? What's not? And what are you willing to keep investing in the gap? The coaching research even hints at why this evaluation is so hard to do alone: coaches themselves acknowledge an economic incentive to keep clients dependent rather than self-reliant, which is exactly backward. The whole point of the work — and of the triangle — is to return the assessment to you. My client at the small college found his answer not by winning over the resistant system but by changing mirrors: letting the team he was building, rather than the peers who slowed him down, reflect his leadership back to him. My academic client found hers by noticing that the role she'd been assigned wasn't on her own internal board of directors at all. Knowing the answer to that isn't a defeat. It's information. And information is how you lead.

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So let me ask you what I ask them: which of the three — fit, support, or agency — is most absent in your current environment?