The Three Hills of Leadership
Early in my career, I told my superintendent I felt like I was standing in a valley surrounded by three hills. On one: the community — students and parents, their wants flowing down to me. On another: faculty and staff, with their own wants. On the third: the district office, new initiatives and goals coming from above.
I summed up my job as building principal as choosing which hill I'd die on.
He laughed and said I wasn't far off. But the conversation that followed taught me something I didn't have language for at the time: I could be certain about what was true, and still lack the conviction to act on it. Certainty is knowing which hill matters. Conviction is climbing it anyway, knowing you might not reach the top.
Why the Gap Between Certainty and Conviction Exists
For years I thought that gap was a discipline problem — that with enough willpower, certainty would simply convert into action. It doesn't work that way, and understanding why has become central to the framework I developed in The Leader Within: Executive Coaching of Educational Leaders (Releasing in April 2027), and as I am developing my next book, Identity First Leadership (working title).
Most leadership development lives in one dimension: Doing — skills, strategies, execution. It treats conviction as a performance issue, something you fix with better habits or a sharper plan. But conviction isn't primarily a Doing problem. It's a Being problem. It lives in whether you have an identity sturdy enough to act from — one that doesn't collapse the moment a hill turns out to be the wrong one, or the moment someone on another hill pushes back.
That's the piece missing from most advice about "choosing your battles." You can be certain a battle is worth fighting and still find yourself unable to fight it, because the part of you that would have to stand on that hill hasn't been built yet.
Three Hills, Three Dimensions
Looking back, my three hills map cleanly onto a structure I now use with coaching clients: Being (who you are, prior to any role or title), Doing (what you produce and how you execute), and Relating (how you show up with the people around you, and how they experience you). The community and faculty hills were pressures in the Relating dimension. The district office hill was largely Doing — initiatives, metrics, goals. But the hill I actually had to decide from was Being: which version of myself was I willing to stand behind, regardless of which direction the pressure came from?
Leaders who never do that interior work don't lack conviction because they're weak. They lack it because no one ever asked them to locate a self apart from the roles pressing in on them from every hill. When that identity work hasn't happened, certainty stays abstract — true, but not yet something a person can stand on.
The valley doesn't go away. But once you know which hill is actually yours to die on — not because the community demands it, or the district office does, but because of who you are — conviction stops being a mystery and starts being a decision you're equipped to make.
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