I Stopped Asking "What's Your Greatest Strength?"

I used to ask it. Every hiring manager asks it. "Tell me about your greatest strength." The answers are always good.

They're rehearsed, competent, and tell me almost nothing that matters.

Somewhere around interview forty of a particularly important search, I stopped.

The question I replaced it with: "Tell me about a decision you made that you're still not sure was right."

The difference in what came back was not incremental. It was a different category of information entirely.

What the Old Question Gets You

Greatest strength questions are a rehearsal evaluation. You learn how well someone has prepared, which is somewhat useful.

You learn which strength they've decided to lead with in a professional context, which is mildly interesting.

You do not learn how they think, how they handle uncertainty, or what their relationship with their own fallibility looks like.

The leaders who have impressed me most over 28 years are not the ones who had the clearest greatest-strength narrative.

They're the ones who could sit in the complexity of a hard decision, where good information was unavailable and the stakes were real, act anyway, and then carry that decision forward with integrity while remaining open to being wrong.

That capacity is not visible in a greatest-strength answer. It is extremely visible in how someone talks about a decision they're still not sure about.

"You don't learn how someone leads from their highlight reel. You learn it from how they talk about the hard calls."

What the New Question Gets You

Some candidates freeze. That's data, leaders who can't access their own uncertainty in a low-stakes conversation rarely access it productively in high-stakes ones.

Some candidates give you a failure story that's really a success story in disguise; "I pushed too hard for excellence and the team found it demanding." That's also data.

The candidates who give you a real answer, who can describe a specific decision, the information they had, what they chose, why they're still uncertain.

And what they've taken from it, those are the people I want to understand more.

Because the quality of thinking in that answer is a direct preview of the quality of thinking they'll bring to every hard call they face in the role.

Two Other Questions I've Added

"Tell me about a time you changed your mind in public, after already committing to a position." This surfaces intellectual honesty and the willingness to prioritise getting it right over being seen as right.

"What's the most important thing your last team needed from you that you weren't always able to give?" This surfaces self-awareness about gaps, not manufactured humility, but genuine accounting.

The best hiring conversations feel like a genuine exchange of information. If the candidate isn't learning anything about you and the role, you're not having the right conversation.

I'm not saying never ask about strengths. I'm saying ask the questions that surface the thing you actually need to know: what it will look like to work with this person when things get hard.

What's one question you ask in every interview, and what would you replace it with if you wanted to see how someone actually leads?

Self-Awareness and Decisiveness are two of the twenty traits in Half & Half.

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