Have you ever had a ‘bad’ working experience? Ever wondered what you would say if you were asked the question “have you ever had a bad working experience?” in an interview? It’s one of the trickiest questions to answer and also one of the most telling for an interviewer.

Most interviewers would have faced similar experiences in their working life. They don’t however need to know the finer details of these experiences, therefore careful thought and preparation is required prior to any interview to work out how you would frame these answers if you are asked the tricky questions.

To help you understand the type of questions which may be asked, UCGR has put together a few example scenarios and questions.


  • Have you ever experienced working for a ‘bad’ boss?
  • Had troubles with work colleagues?
  • Did not like the work or the work was not what you expected?
  • Worked somewhere where the environment or culture was not desirable?

Questions you may be asked about these type of scenarios:

  • Tell me about a time when you did not agree with the direction your boss gave you.
  • Have you ever had a bad boss experience? Can you tell me about it and how you overcame this?
  • Tell me about a time where you had a work colleague that you did not get along with. How did you resolve this?
  • Tell me about a time where you had a work colleague that did not deliver on their work and let the team down. How did you cope with this emotionally?
  • Have you ever experienced a role where the work was not satisfying, did not stretch you or was not was you expected? What steps did you take once you realised this was the case?
  • Have you ever experienced a role where the work was not satisfying, did not stretch you or was not was you expected? What did you learn from this scenario?
  • Tell me about time when you did not resonate or agree with the work environment or culture you worked in. What steps did you take once you realised this was the case?

You may now be nodding your head thinking I’ve been there and I also have no idea how to explain the scenario in a positive light so the interviewer doesn’t think badly of me.

How to frame an answer to these tricky type of questions:

Firstly never ever ever talk badly of anyone or anywhere you are working at or previously worked for, no matter how terrible the situation was. This will concern any prospective employer. They may wonder how you will talk about their organisation when you aren’t at work.

Think carefully before the words come out of your mouth. If you can hear or feel yourself being negative, slow down and be careful.

Start the answer with setting the scene:

→There was a prior colleague who was very difficult to work with because they didn’t agree with the team’s direction or vision.

Follow by explaining what they did:

→During a project, it almost appeared that they were sabotaging the program or work, always causing rifts in the team, being rude to the customers or drawing out our timelines.

Continue by then explaining what you did about the scenario:

→My manager had asked me to speak with the team member to understand their drivers and vision of how the team worked. Once I got a clearer vision, I then spoke to them about how their behaviours has been impacting me and the team’s output. We then had a clearer view of each other and the goals and objectives of the team.

Close out with the results of the engagement with tangible outcomes:

→Post these conversations, we worked out the concerns and issues the team member was facing and also made it really clear as to how their behaviours were affecting the team outcomes. I started to see a considerable increase in their output and decrease in their sabotaging behaviour. The whole team started to notice and many people commented to me how happy they were. I continued to work with this individual and a few months later, saw a dramatic positive difference upon engagement of a new piece of work. My manager had let me know they were really impressed and my interactions had made a lasting positive difference on the team and the individual.

For bonus points you can add:

What you learnt from the situation or how this engagement will help you in the future.

  • This helped me learn more about people’s differences, how to manage others and that often most difficult people issues can be sorted out with a two-way conversation.

Think about those leaders you have worked with that possess the qualities you admire and share those. Alternatively think about the best team or environment you have worked with or in and share those experiences. This will leave the answer in a strong positive way.

Now you have delivered your answer, it’s very common for the interviewer to ask you a few follow up questions. They may be similar to the below:

  • How did you feel about this experience?
  • How did you deal with the emotional side of the situation?
  • What did you learn from this experience?
  • What would you do differently in the future?

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Hot tips:

Be smart, positive and careful about how you answer a question in relation to bad work experiences.

Never ever talk badly or negatively in an interview about a prior work place, boss or team member, no matter how bad the experience was.

Focus on the learnings you took away from the scenario and explain how you can take those learnings with you to be a better, well rounded individual.

Don’t use emotional or judgemental language.

Don’t focus on your emotions or how you felt in the scenario, unless specifically asked- this is not a counselling session! If you are asked, ensure that you keep your deepest emotions out of the conversation and say something like “It was a trying scenario, however it allowed me to learn a lot about patience, personal growth or how to deal with conflicts.”

If you are ever asked the question ‘why did you leave your last role?’ you should not answer with scenarios such as:

  • Because of my boss
  • I didn’t like my team or X colleague
  • The job was terrible

You get the message! Don’t use scenarios which begin with a negative connotation.

You should focus on growth, development or factors such as a change in industry, type of work, or similar. You could also site reasons such as I was looking for a cultural change.

Whilst we certainly are not at all suggesting you lie, you need to think about how you structure these answers carefully, be truthful, but smart about how much you share as just this answer alone could take you down a path you don’t want to go.

In your career, you will have all sorts of experiences, the good and the bad, providing you the opportunity to learn about yourself.

We’ve seen a great quote from the Simply Hired blog to leave you with:

“While finger-pointing is an unattractive quality in an interviewee, self-reflectiveness and self-understanding are both very attractive qualities. Exhibit those instead”

Good Luck with those tricky ones!

UC Grad Recruiter