The Hire You Almost Didn’t Make

THE PRINCIPAL’S CHAIR

Leadership decisions from the real world of schools and organizations.

Issue #104

The Hire You Almost Didn’t Make

She wasn’t the obvious choice.

Her resume was thin compared to the other two finalists. Four years of teaching, no advanced degree, nothing on paper that made her stand out from the stack. When my assistant principal reviewed the candidates, her folder ended up on the bottom. That’s almost always where she would have stayed.

But something in her interview stopped me.

I’d asked every candidate the same question: “Tell me about a student you failed.” Most people flinched, recovered, and then told me a story that was really about how hard they’d tried. Understandable. Human. Not what I was looking for.

She didn’t flinch. She looked at me for a moment and then told me about a ninth grader named Marcus — specifically, painfully, and without a single hedge. No pivot to the silver lining. Just honest accountability and a clear-eyed understanding of what she wished she had done differently.

I hired her!

Seven years later she was one of the finest teachers I’ve ever watched work with at-risk students. Marcus had moved on by then, but she carried him with her into every classroom after that. You could see it in how she taught — the way she stayed a little longer, asked one more question, noticed the kid in the back who was starting to disappear.

Most hiring decisions — in schools and in organizations of every kind — over-index on credentials and under-index on character. That’s not because leaders are foolish. It’s because credentials are easy to measure and character is uncomfortable to probe for in a forty-five minute interview. So we default to the transcript, the degree, the years of experience. And we miss the person sitting right in front of us.

But there are questions that crack the window open. “Tell me about a student you failed” is one of them. So is “Tell me about a time you disagreed with a decision your supervisor made and what you did about it.” And simply: “What are you working to get better at right now, and what are you actually doing about it?”

The answers matter less than what the person does with the question. Do they go somewhere real or do they manage you? Do they sit with the discomfort or perform their way around it? Do they talk about growth like it’s a goal they’ve set, or like it’s something they’re genuinely living?

The best hires I ever made shared one quality above everything else. They were more interested in getting better than in looking good. That distinction sounds simple. In practice it’s rare. And in a school — where the stakes are children and the margins for mediocrity are thin — it’s everything.

THE TRANSFERABLE PRINCIPLE THIS WEEK

In your next hire — for any role, in any organization — build at least one question into the interview that has no comfortable answer. Then watch what the person does with the discomfort. Credentials tell you what someone has done. That moment tells you who they are. Hire who they are.

Until next time — the chair is yours.

Next issue: The board meeting that almost ended my career — and what I did in the parking lot afterward.

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