Common interview question: “Tell me about a time when you had to work with a difficult boss or manager?” / “Tell me about a difficult boss you’ve had in the past?”
Why they’re asking: (If it’s your potential future boss asking) They want to make sure that former bosses that you’ve found to be difficult aren’t similar to them/their work-style. (If it’s the recruiter or someone else) They probably know the work-style of the person you may end up reporting to and want to make sure you are compatible. In general, people also want to make sure you can work with challenging people in a way that is professional.
Why it’s tricky: As with all negative interview questions, you need to find a way to be diplomatic when answering the question. Let’s face it, everyone’s had a challenging boss at one time or another!
How to answer…
Make sure you actually answer the question
I’ve said this before… avoiding the question is never a good way to deal with any interview question – especially the more “negative” ones. You need to show in your interview that you are comfortable being honest and self-aware and if you refuse to avoid all negative questions, it comes off as very disingenuous.
Like I mentioned above, everyone has had a difficult boss at one time or another so there’s no need to pretend your working relationships have always been 100% perfect. If you haven’t necessarily had a difficult boss (because of limited work experience) you can say, something like “I’ve been very lucky to have great bosses but… I’ve definitely had to work with difficult people who I didn’t directly report to” or “Even though my boss was great, it was sometimes difficult to work with him or her on X type of projects because…”
Again, pretending you’ve never had conflict with a superior in the workplace is like saying you don’t have a weakness, and it doesn’t reflect well!
Be very, very diplomatic and do not get defensive/emotional
With negative questions (and you can expect a few of them in any interview) you have to make sure you are really diplomatic. Basically, do NOT throw anyone under the bus, place tons of blame, or “trash talk”. If you’re doing this to your previous boss, what will you say about your next one??
Answering difficult questions in a diplomatic way can be a challenge, but I’ve seen it done successfully by many candidates. In speaking about your boss, you can always start the answer by sharing a strong point (i.e. “While my boss was great at X, we had a challenge working together on Y.”
Then always end on a positive note about what you are looking for in a boss/manager in the future. Example: “Based on this, it’s really important for me to have X, Y, Z in a future manager.”
Show off your “professionalism” and problem solving capabilities
Dealing with challenges in a way that is professional is a HUGE plus and reflects very positively on you. With all “negative” questions there is a great opportunity to show that you’ve handled tough people head on in a way that didn’t create a negative working environment. Take this opportunity to share how you have dealt with a more challenging boss.
In the example we used before, you might say something like “Knowing training was not necessarily something my boss wanted to spend time on, I found a way to ask questions when he/she wasn’t busy or when we had scheduled time. Even though it wasn’t always ideal, we found a way to work really well together.”
Difficult bosses are pretty common in the workplace but that doesn’t make them “bad bosses”. I think a great way to approach this question is coming at it from a perspective of “we had different work styles” versus “I’m wonderful and they’re the worst!”
