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How to answer tricky interview questions: have you ever had a bad experience with an employer or colleague?

Jaymes Carr

Don’t get caught out: we give you tips on how to answer tricky interview questions about bad experiences: how to be professional and answer successfully.

Some people are very lucky: they have excellent experiences throughout their career and go home at the end of the day with few, if any, complaints about their colleagues or the people they work for. But most employees will have a story to tell about the boss who disappointed them or the co-worker who was a pain in the neck: so, how do you go about discussing it with a future employer?

What makes this a tricky question?

Talking about negative past work experiences is a minefield, and it’s all too easy to bungle your answer in a way that casts a pall over your application. Here are four things you should know about the question before going into an interview.

First, the question is a test of your professionalism: however bad your past experiences were, it’s never a good idea to badmouth a past employer, or come across as aggressive or unreasonable.

Second, the question must be handled in a way that doesn’t arouse any suspicions that, really, the problem you describe was caused by your own professional or behavioural shortcomings.

Third, it’s not a good idea to give the impression that your working life so far has involved a pattern of interpersonal conflicts, regardless of whether or not you were responsible for them. While most people probably have one or two negative work experiences to share, it doesn’t bode well to be the candidate with an endless list of them.

Finally, in discussing a previous work environment, you must take into account that prospective employers might hear the other side of the story when making follow-up calls or checking references. You certainly don’t want to bring up an issue that generated major conflict, different versions of events, or punitive action that could impede your career progress.

What is the interviewer really asking?

As with so many tricky questions, the request for information about past workplace conflict is designed to help interviewers establish several things:

1. How professional are you?

Did you navigate your difficult working relationship with maturity and tact? Are you able to provide the facts without making personal judgements? And did you seek recourse via appropriate channels?

2. Do you communicate effectively?

If you did attempt to resolve the situation, how did you make your feelings known? Can you discuss the experience now in a professional manner?   

3. Can you think on your feet?

Interviewers know this is a tricky question: difficult experiences are often difficult to talk about, and you’re under the added pressure of wanting to make a positive impression in a job interview. Can you handle it?

4. Do you have the ability to look for positive outcomes even in difficult situations?

Let’s say you really did have a rotten boss or worked alongside a bully: it happens, and you certainly don’t need to let it torpedo all of your future job interviews. So, if you’re going to bring it up, focus on the constructive and reasonable ways in which you sought to address the situation.

Crafting a strong response

It’s particularly important that you approach this question with professionalism and practicality. Describe the situation in a neutral way, without engaging in trash talk or unseemingly self-justification. Most importantly, focus on the positive: what were you able to learn, even if you found yourself in a truly difficult situation?

Take responsibility: not for the behaviour of another person, but for your reaction to it. Show that you are able to shoulder the blame, where appropriate, but also that you have clear professional expectations.

Finally, it’s generally better to attribute any examples you provide to different work styles or priorities, instead of blaming a personality clash (in which case it’s a lot more difficult to avoid implicitly assigning blame).

For example, here is how a candidate might discuss the experience of working for a boss who didn’t provide a lot of feedback:

“Things started a little shakily at my last job, because I didn’t feel as if I was getting enough feedback to know if I was meeting performance expectations. However, I was able to communicate this to my boss, who subsequently arranged weekly catch-ups. Very quickly, we developed a close working relationship, and I learned a lot from him about the decisions that face business leaders.”

Here is how another candidate might describe a situation in which they couldn’t reconcile their differences with a past employer:

“I didn’t see eye to eye with my last boss, which led to ineffective communication between us. In retrospect, I think my relative lack of experience, and reluctance to ask questions that might be perceived as silly, played a role. However, this didn’t stop me from accomplishing several outstanding results, such as when I spearheaded an initiative that increased sales in my departments.”

Tricky interview questions about past bad experiences can be challenging, but by understanding what they really want to know, and with careful consideration, you can answer this question with ease. Want to learn more about navigating tricky interview questions? We give you tips on what to say when you are asked to explain how you’ll be successful in your new job.