Who Can Say Yes: Matching People to the Right Challenges

When I interview, I’m not trying to “sell” anyone on a role.

I’m looking for individuals who can genuinely say yes to an organization’s real challenges and opportunities.

Because the same environment that energizes one person will overwhelm another.

Years ago, I led a search for a major university. The dean was brilliant — and intimidating. Previous hires had struggled under such a powerful personality.

After hundreds of conversations, we found someone different: calm, confident, thoughtful, unflappable. They knew how to challenge respectfully and wouldn’t be rattled easily. That alignment mattered — they stayed five years and had a major impact.

That’s the work of hiring: understanding who thrives with a certain leader and who won’t, no matter how impressive they look on paper. Fit isn’t about likeability — it’s about compatibility with reality.

I’ve talked more people out of roles than into them. If retention is the goal, honesty (on both sides) is non-negotiable.

If you’re a hiring manager, ask yourself: What does someone truly need to say yes to in this role — and who is built for that reality?

And if you’re a candidate, ask: What environments bring out my best, and where am I saying yes for the wrong reasons?

The answers determine whether someone stays for 18 months — or five years.