Tell Me a Time You Failed

Every candidate walks into an interview with their hero story ready. Those stories are prepared, polished, and practiced. They tell you something. But they don't tell you everything.

So at some point in most interviews I conduct, I ask a different question: tell me about a time you failed. Not a challenge you overcame. A genuine failure. The room changes when I ask it.

The first type I call fake failing. It sounds like self-reflection but isn't. Watch for it. It's like someone fake-running across a crosswalk. The motion is there. The urgency isn't.

The second type: no failure at all. The candidate pivots, hedges, or simply can't find an example. Move on.

The third type is rare. We were interviewing for a country manager role. The candidate told us about coaching his seven-year-old's rugby team. After a pressure-filled week at work, the kids were distracted. He raised his voice. And immediately regretted it.

We hired him.

The failure question isn't a trap. It's an invitation to be honest. The candidates who accept that invitation are the ones worth knowing better.