Why I keep asking new senior hires about their last bad week

There is a question I have asked every senior hire I have made in the last seven years. It comes near the end of the interview, when the candidate is relaxed and the structured competency questions have been worked through. I ask about the worst week they have had at work.

The framing matters. I am not asking about a failure. Asking about a failure produces a rehearsed answer about a project that did not land and what they learned from it. I am asking about a week, by which I mean five working days, in which the work itself was bad. The colleague who left without notice. The system that went down for two days and nobody quite knew why. The regulator who arrived earlier than scheduled. The auditor who flagged something material in the last week of the audit.

The answers fall into three categories, and they are diagnostic.

The first category is the candidate who has never had a bad week. This is a candidate who has not been close enough to the operating layer to feel one. There is nothing wrong with them. They are also not yet ready for the role I am hiring them into. Senior operating roles are bad-week machines. A candidate who reaches for an example from their MBA is telling me they have not yet been the named owner of anything that mattered.

The second category is the candidate who recounts a bad week and describes the people around them. The colleague who let them down, the team that did not pull together, the system that was inadequate. This is often a true description. It is also a category I have learned to be careful with. Senior roles require a candidate who can hold the responsibility for the bad week even when the failure was someone else's. If the entire narrative is external, the candidate's working theory of accountability is going to slow the rest of the team down.

The third category is the candidate who describes a bad week and talks about what they did during it, what they would now do differently, what they have changed in how they work since. The answer does not have to be elegant. Often it is a little embarrassing. What I am listening for is the structure of the recollection. They have been the named owner. They know what was theirs. They know what was not. They have done some unromantic, post-week thinking about it. This is the candidate.

There is a fourth answer I should mention, which is rare and worth knowing about. Some candidates answer the question, then add an unprompted observation about what they had to choose not to do during the bad week because they were dealing with the bad week. That answer is almost always given by candidates who have run a real operation. The bad week reveals the prioritisation muscle, not the resilience muscle. The candidate who can describe the trade-off has already done the job at the level I am hiring for.

The bad-week question is not the only thing I rely on. It is the most reliable predictor I have found. It is also the question most candidates have not been coached on, which is part of why it works.