Why I Don’t Ask Senior Candidates About Their Failures

And the one question I ask instead.

There’s one question almost every HR-led interview process insists on.

“Tell me about a time you failed.”

At junior level, it sometimes earns its keep. At C-suite, it’s a junk question. And it’s almost always the wrong thing to ask in the room.

I’ll explain why I won’t ask it. And then I’ll tell you what I ask instead.

What the question actually produces

Watch what happens when you ask a senior candidate to “tell me about a time you failed.”

They take a breath. 

They think for a moment. 

They give you a story about being too driven. 

Or about taking on too much. 

Or about a project that ultimately succeeded but at a personal cost they’ve since learned to manage.

In other words: they dress a failure up as a personal strength.

That isn’t because they’re being evasive. 

It’s because the question puts them into a defensive crouch. At senior level - where the stakes are tenure, reputation, and a public exit narrative - you don’t get rewarded for unguarded honesty in front of a hiring panel. You get rewarded for the candidate version of “what’s your greatest weakness?”. A dressed-up failure that protects the brand.

The interviewer walks away thinking they tested for self-awareness. 

They didn’t.

 They tested for the candidate’s ability to perform self-awareness under pressure, which is a different and much less useful thing.

Why the question doesn’t fit the room

The deeper problem is structural.

Competency-based interviewing was designed for high-volume, junior-level hiring. It works when the interviewer is genuinely more experienced than the candidate, when the candidate is expected to follow the interviewer’s lead, and when the questions exist precisely to surface things the candidate hasn’t yet learned how to discuss.

At C-suite, none of that is true.

The candidate in front of you has, in many cases, run organisations larger than the one they’re being interviewed for. 

They’ve probably interviewed more senior people in their own career than you have.

The rhythm of the conversation should be peer-to-peer, not parent-to-child.

When you ask a senior leader to “tell me about a time you failed,” the rhythm collapses. You’ve put them back into junior-interview mode. The conversation stops being a real exchange of professional judgement and becomes a performance.

You don’t learn anything you couldn’t have learned from their CV.

What I ask instead

There’s a much simpler reframe.

After we’ve talked through what’s gone well in their career - the wins, the launches, the appointments, the turnarounds - I ask the same insight a different way.

We’ve talked about what went well. What didn’t go as planned, and what would you do differently?

That’s it. 

Same territory. 

Different power dynamic.

The reframe matters because it puts the candidate on the front foot, not the back foot. It signals that the conversation is constructive, not adversarial. 

And, most usefully, it gets them away from prepared “weakness” answers and into the territory where the real learning actually lives.

What I’m listening for in the answer isn’t the failure itself. 

It’s the specificity. 

A senior leader who has genuinely learned from something can describe what they would now do differently in two or three sentences, in operational detail. 

A senior leader who hasn’t, can’t. 

They retreat to generalities. 

The wider their answer, the more they’re improvising.

That diagnostic is far more revealing than anything “tell me about a time you failed” was ever going to give me.

“But isn’t that just a nice conversation?”

A hiring manager put this back to me directly recently, and it’s a fair pushback.

If you treat a senior interview as a peer-to-peer exchange - and you take “tell me about a time you failed” off the table, doesn’t the conversation drift into something too friendly to be useful? 

Two professionals walking away feeling good about each other but no closer to a decision.

The honest answer: yes, that’s the risk.

The structural protection against it isn’t to put failure questions back into the script. 

It’s to do the work before the interview.

The first building block of any senior hire is the question I ask on every mandate, before a search even begins. What problem are you solving by hiring this person?

If that question has been properly answered, and most of the time, in my experience, it hasn’t - then the senior interview has a spine. You know what behaviours you need to see evidence of. You know what kind of context the candidate has to have lived through. You know which experiences you’re going to test for specificity, and which you’re going to take at their word.

That gives the conversation its professional weight. 

Not the trap question about failure.

The pattern in summary

When you ask a senior candidate “tell me about a time you failed,” you teach them that the room rewards prepared, dressed-up answers.

When you ask them “what didn’t go as planned, and what would you do differently?”, you teach them that the room rewards specific, learned, operationally honest answers.

In twenty years of senior hiring, the second kind of conversation is the one that has produced the appointments that aged well.

The first has produced a lot of polished applicants. 

And quite a few quietly disappointing hires.

Before your next senior interview, ask yourself this

Look at the last senior interview process you ran.

How many of the questions were designed to make the candidate feel like a peer you’d be working with?

And how many quietly slipped them back into a parent-child interview rhythm they outgrew twenty years ago?

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If you’re scoping a senior appointment and want to walk through the brief before you sign off the interview structure, I’d welcome the conversation.