IT projects are [in]famous for going off course. Impossible deadlines, lack of resources, miss-management… the list is endless. IT is also often guilty of sweeping these mistakes under the carpet and you need to decide whether you will hire people who will continue to allow that to happen or call out these detours before they go too far. This question will both prompt the candidate to consider whether they have ever really stood up against what they think is 'bad IT' in the past, and also whether they would do so in the future. Beyond calling out possible problems, you also want to assess their ability to take ownership and seeing the resolution out, as just pointing out faults and expecting others to deal with them can often be more hindrance than help.