As an interviewer, asking a candidate to tell you about the best boss and the worst boss they ever had can be quite revealing about their attitude towards authority. Some things to look out for in the candidate’s response to this question are:
- When describing their best boss, does the candidate mention the boss’s willingness to coach them and to help them learn and grow? This may indicate their desire to learn and can be probed further
- Do they mention that the good boss pushed them hard but gave them credit and recognition for doing a good job? Again—perhaps an indicator that they value recognition
- Do they focus on describing the good boss as easy going and friendly? This may raise a red flag to investigate further regarding the candidate’s attitudes towards working for a highly directive supervisor
- When talking about the worst boss, does the candidate get into the blame game—accusing the ex-boss of causing them to fail? This raises a red flag about the candidate’s willingness to take accountability for their own performance and, at the very least, shows the candidate’s lack of political savvy.
A great follow-up question is to ask, “looking back now, is there anything you could have done to improve your relationship with your supervisor?”
A smart candidate will use this as an opportunity to demonstrate how much they have learned since having this experience with a past boss and will try to make points such as:
- At the time, I thought my boss was being over critical of me but I can see now that he was giving me useful feedback—I am much better at accepting feedback now
- I now understand more about the pressure my supervisor was under at the time and I can see why he might have appeared so abrupt
- If the candidate comes back with a comment such as, “no, there was nothing you could ever to please that SOB”, it may provide another red flag to follow up on regarding their attitudes to authority.
Use broad open ended questions as part of your interview technique—using this technique can get the candidate talking and they may unintentionally reveal strengths and red flags that you might otherwise miss.
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