The best candidates for Head of School or Senior Administration roles pursue leadership not as a step up, but as a step into purpose. 
If one has ever had the pleasure of falling in love with another person, they don’t just think it; they feel it. Conversations that stretch long into the night still feel too short. They might catch themselves smiling for no reason, energized by the thought of “what could be” and a steady dose of, 'Yes, this is it.' That certainty is what makes commitment possible.

Some may think this is a stretch, but the same is true in a Head of School or senior administrator search. A candidate who truly wants the role doesn’t just answer questions well they light up when they describe their interest in community, lose track of time when talking about teaching and learning, and bring energy that makes people lean in. That kind of conviction cannot be faked.

When Conviction is Missing, it Shows
A candidate may hedge when asked about the challenges of the role, offering cautious or vague answers. Or they may pursue the position for all the wrong reasons: because it feels like the logical next step, because they love the location, or because colleagues and mentors told them they “should.” But true leadership is not about advancement for its own sake. It requires a deeper motivation, a genuine pull toward the work, the community, and the responsibility. When that conviction is absent, the gap between what a candidate says and what they genuinely want quickly becomes visible. And in a competitive search (which these all are!), that lack of clarity is all it takes for another, more certain candidate to move ahead.

How to Know You’re Ready?
Before entering a search, it’s worth asking yourself a few hard questions. Can you truly picture yourself leading this community every day? Are you energized by the prospect of difficult decisions and long hours, or simply intrigued by the title? Do you want the work enough to withstand the inevitable stress and scrutiny? This is not an exhaustive list, but if your answer to any of these questions is lukewarm, it’s a sign to pause and reflect before jumping in. A half-hearted job search rarely ends well.

What Schools Look For in Conviction
Search committees are drawn to leaders who speak with specificity about their emerging vision, show genuine curiosity about the school’s people, history, and culture, and convey enthusiasm rather than obligation when discussing the demands of the role. They notice when candidates share stories of resilience, highlighting not only what they accomplished but how they grew through challenges. In short, they look for passion that feels lived, not rehearsed.

The Bottom Line
A Head of School or Senior Admin search is not the place to test whether you might want the job. It’s the place to step forward once you know you do. Just like falling in love, certainty is what sets everything else in motion. Advancement may carry you upward, but conviction is what makes others want to follow.