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How to Answer Job Interview Questions About Your Last Boss

Jules Halliday is an author, public speaker, career coach, and business development trainer with over 20 years of experience.

Even if your previous boss was the devil in disguise, it's important not to speak negatively about them!

Even if your previous boss was the devil in disguise, it's important not to speak negatively about them!

How to Discuss Your Previous Manager, Boss, or Supervisor

This is where walking on eggshells would be advised. Even if your previous manager or supervisor was the devil in disguise, you should always avoid negativity, insults, or defamatory comments. The person sitting right in front of you will not take kindly to you moaning about your previous boss, and the chances are they will presume you may one day talk of them in the same light.

“Who Was Your Best Boss and Who Was the Worst?”

Keep this as a positive and respectful answer. If you liked all your previous managers, then you are very lucky. If not, then try to think about at least one thing you may have learned from the not so nice ones.

  • “I've learned from each boss I've had. The good ones have taught me how to be an inspirational leader whereas I have discovered from those I would deem as weaker managers, what not to do.”

If you are interviewing in the same town as your previous company or even in the same sector, don’t forget that your old boss might actually be a friend or acquaintance of the interviewer!

“What Was It Like Working for Your Supervisor?”

I would suggest you keep this answer brief and positive. Highlight anything you felt your supervisor did to get the best out of you. Did he or she teach you anything in particular? Would you regard them as a mentor?

  • “My supervisor was very hands-on and was always there to support my colleagues and me.”
  • “He/she allowed us to work in an autonomous manner but had regular meetings with all employees to monitor their progress.”
  • “My supervisor always ensured that the working environment was fun but professional.”
  • “I have learned a great deal from my supervisor as she was very customer focussed and had an empathetic manner when dealing with complaints.”

“What Do You Expect From a Manager?”

This question could be asked in a few other ways, as well:

  • “Describe your ideal boss.”
  • “What does the perfect manager look like?”

This question is often asked to gauge how you respond to supervision and authority. The interviewer also may try to visualise how you will respond to requests from the current manager and their superiors.

Either way, your answer should be based on what you perceive or have found out about the level of supervision required in the role. You don’t want to come across as someone who needs to be micro-managed if the role is mainly autonomous.

Try to strike a balance between someone who is able to work independently yet responds positively to specific instruction.

You may be able to find out more about your new supervisor in advance. Quite often the job description will detail who you will directly report to so you can do a bit of homework in advance.

What is their background? Do they have a Linkedin profile you can research?

Do you know anyone in the company who knows the supervisor and their management style?

Being armed with this information can stand you in good stead. You don’t want to be discussing that you like a supervisor who makes the work environment a laugh a minute if the truth is he/ she is a serious taskmaster.

If you really can’t find out any information then good general answers would be:

  • “I am at my most productive when a supervisor has good connections with the rest of the team and is there to support, mentor and guide me to succeed.”
  • “I feel the best supervisors are those who are passionate about the brand, their team and the customers/clients.”
  • “I appreciate a supervisor who recognises that every member of the team is different, has something to contribute and shows no favouritism.”
  • “I would expect my supervisor to be open and honest with me if there are aspects of the role I can improve upon or do differently with my work. I would also like to feel confident that I can talk to them in confidence if I have any issues relating to my work.”

Never under any circumstances criticise a past manager, and try to avoid describing your ideal supervisor as superhuman!

You may like to prepare deeper answers by having some examples of how you have worked well under the supervision of a variety of managerial styles.

“Have You Ever Had Difficulty Working With a Manager?”

Here are some more variations on the same question:

  • “Tell me about a time when you have had a disagreement with your boss.”
  • “Have you ever had a conflict with a superior at work and if so, how was it resolved?”
  • “If you know your boss is 100% wrong about something, how would you handle this?”

If you have indeed had difficulties with a previous boss, you must be very careful with your answer. However, understand that at some point, most employees have some sort or disagreement or difference of opinion from their manager, so it is perfectly acceptable to discuss the situation providing it was resolved and you had learned from the experience.

Differing opinions can in some circumstances be positive if opened up to debate in order to change processes in a positive way for the greater good of the company and its staff.

If you have an example from a long time ago, then choose that scenario as your answer. The further into the past the better.

  • “Early in my career I had a manager who I didn’t get along with. We just didn’t seem to see eye to eye, but now I realise this was a combination of my lack of experience in the workplace and a breakdown in communication. We had different expectations and I felt that by asking questions it was a sign of weakness and inability to do the job. Now I always ensure that I find common ground with anyone I work with and ask questions immediately if I need clarity on a subject or instruction.”

Some interviewers may press on this question as they may find it hard to believe if your whole career relationships have been perfect and without conflict.

  • “Yes, I have had conflicts in the past but not major ones; more differences of opinion. The way I deal with these is to fully listen and understand the other person’s perspective then work together to come up with a solution. I find that if we can identify a common goal then the solution is easier to find.”

Buzz words to use in these types of answers are respect, solution, identify, listen, resolve and so forth.

Always ensure that you give brief detail on how any situation was rectified so the interviewer can see you are accountable and don’t hold any grudges.

“Would Your Current Boss Describe You as Someone Who Goes the Extra Mile?”

More variations of this question:

  • “Give me an example of when you have been proactive in a task that wasn’t in the job description.”
  • “Would your boss say you are dependable/ flexible/ reliable?”
  • “Tell me about a time when you have gone over and above the call of duty.”

Of course, you would like to answer “Yes” to these questions and give examples, so how can you elaborate?

Can you think of any compliments you have had from your boss or any clients and customers?

How was your last appraisal? What were the most positive things your boss spoke about?

  • “I was thanked by the company bosses recently in recognition of me covering extra shifts due to some staff being unable to work due to the heavy snow.”

Can you give any examples of when you have been dependable, proactive or even innovative?

What have you done that nobody else has? What did you do first before everyone else copied you?


“What Would Your Current Manager Say Are Your Strengths?”

We often find it hard to tell people what we’re good at.

Selling yourself without appearing arrogant is one of the most common interview worries. Many people simply don’t sell themselves for fear of seeming big-headed.

Do you know what your strengths are? You’d be surprised how few people do.

One place to start is your recent performance appraisals. What did they highlight as your strengths? Can you supply evidence (provide examples)? Can you relate the strengths to the position you’re being interviewed for?

Still stuck for answers to this question?

You could try asking someone. Ask a trusted friend or work colleague. Make sure they give you examples of where you have demonstrated the strengths, so you can quickly use these, if asked.

It’s also worth revisiting the job information to look for which competencies they are looking for. You will make a more favourable impression if you can cover some of these in your answer.

“What Would Your Current Manager Say Are Your Weaknesses?”

This is not the place to admit your biggest flaws.

It’s also not the time to pretend you don’t have any development areas—it would make you look either conceited or as though you can’t evaluate your own performance.

So how should you handle this type of question?

The main thing is to admit that you have areas to develop, whilst showing that you are already working on them and giving examples of the progress you have made.

If possible, choose a development area that doesn’t affect your ability to do the job for which you are being interviewed.

It’s usually a good idea to make the “weakness” something small. Avoid topics such as “organisational skills” or “time management”!

What happens if one of your development areas is one of the key strengths required for the role?

Make sure you can demonstrate why it won’t be a problem.

“How Do You Take Direction?”

The interviewer is trying to ascertain whether or not you can be managed and follow instruction without high drama.

Your answer to this question should include that you understand that you should follow instructions from your supervisor and have the confidence to ask questions should you require further clarity.

“Describe a Past Conflict With a Supervisor. What Would You Do Differently Today?"

At some time, most people have had an experience where working with their supervisor wasn’t all plain sailing. If you haven’t then say so but do try to use an example of either when you haven’t worked well with someone in authority in a non-work setting or speak of a time when you noticed a colleague overcome this and what you learned from your observations.

If you have had a time when you didn’t work well with a supervisor, then be honest. However, avoid all references to negativity or blame. Answer the question clearly with most of the detail being on the latter part of how you would have changed the outcome. The interviewer is looking for accountability on your part. If you had a rough time then that’s ok but it’s what you learned and how you will work to avoid a similar situation in the future that counts.

If you have more than one example, then it is normally best to either choose the situation where you had a positive outcome or the one earliest in your career.

Whatever You Do...

Whatever you do or say regarding your old or current boss, manager or supervisor, keep it factual, relevant and positive.

Practise in advance how you may answer these types of questions so you sound sincere but not over-rehearsed.

Finally, look on the bright side; you are leaving the old boss behind!

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This article is accurate and true to the best of the author’s knowledge. Content is for informational or entertainment purposes only and does not substitute for personal counsel or professional advice in business, financial, legal, or technical matters.