Answering Difficult Interview Questions

by Lisa McGrimmon

The most difficult interview questions to answer for most people are ones that ask about a negative or challenging situation.

"Tell me about a time when you had to work with a difficult colleague."


"Tell me something you didn't like about your last boss."

Questions like these ones frequently trip people up and cause people to say all sorts of negative things that completely take them out of the running for the job.

However, if you know a few simple strategies, it is easy to turn these difficult interview questions around to prove to interviewers that you are an effective problem solver who can handle challenging situations.

The type of questions we're talking about here are negative, situational questions.

A situational interview question is simply a question that asks about how you handled a specific situation in the past. It is particularly challenging to answer this type of question well when it focuses on a negative situation.

Frequently employers will ask you to describe a time when you had to deal with a difficult:

  • customer or client
  • employer or
  • co-worker

Tough Questions That Employers Like to Ask

The most difficult interview questions employers ask

There are other challenges an employer might ask about, but the examples above are quite common.

The specific way the employer phrases the question may vary from interview to interview, but the essential questions and the best strategy for answering them remain the same.

Employers may phrase difficult interview questions in a way that is more specific to your line of work.

For example, if you worked in social services, the question, "Tell me about a time you had to deal with a difficult client." may become, "Tell me about a time when you worked with a client who was at risk for suicide." It is, in essence the same question, but it is more specific to that particular field of work.

Related: How to predict tough questions an employer might ask based on your industry and work history

Avoid These Big Mistakes

Remember, you do not have to (and you shouldn't) tell the employer about the worst situation or the most obnoxious, annoying person you ever had to deal with at work.

If the Problem Was Never Resolved, Don't Talk About It

The biggest mistake people make when answering these difficult interview questions lies in talking about a negative situation that was never resolved.

In order to answer this type of question well, you need to describe a situation that was challenging and you handled it well and created a positive outcome.

If You Are Still Angry About It, Don't Talk About It

If you are still angry about a specific person or situation, do not talk about that person or situation in a job interview!

If you dealt with a difficult situation that was never resolved in a positive way, do not talk about that situation in a job interview!

Instead, talk about a situation that was challenging, but as a result of your smart thinking or hard work, the situation was resolved.

Don't Try to Dodge the Question

The other mistake people make when answering this type of difficult interview question lies trying to avoid the question completely.

Sometimes, in order to avoid mentioning something negative in a job interview, people will say that they have never worked with a difficult co-worker, or there was nothing they disliked about their former employer.

The problem with this answer is two-fold. First, the employer will think you are being evasive. Almost everyone deals with a difficult customer, co-worker or employer at some point, so saying you have never come across these situations sounds insincere.

Second, by saying you have never dealt with a challenging situation at work, you are not showing that you have the ability to deal with challenging situations in a way that is effective.

There's nothing wrong with admitting to an interviewer that you have encountered challenges at work, as long as you took appropriate steps to resolve the situation effectively.

A Simple Formula for Answering Difficult Interview Questions

How to answer the toughest job interview questions

Here's a formula that is very effective for answering this type of question:

  1. Think about a challenging situation at work that you resolved effectively and that does not make you feel angry
  2. Describe the situation
  3. Describe the appropriate steps you took to resolve the situation
  4. Be sure to highlight the positive results of your actions
  5. Repeat! Be prepared with great responses to questions about a difficult boss, colleague and client/customer. All three of these questions are all extremely common.

Related: Using the STAR technique to answer tough questions

Sample Answer


"Tell me something you didn't like about your last employer."


"I really liked my last employer, but there was an awkward situation in the office that I was able to resolve.

I worked as a legal secretary in a small office. One of the lawyers in the office frequently got into loud, heated conversations on the phone. He normally left his office door open, so everyone could hear what he was saying. It was distracting for staff who were trying to concentrate and awkward for clients who could hear in the waiting area.

No one in the office seemed to know how to handle the situation.

I casually mentioned to this person that I noticed sometimes, when he was on an important call with his office door open, he might need a little privacy. Then I asked him if he would like me to come over and close his door for him whenever I noticed he was on a call like that.

He agreed and was pleased with the suggestion. I was able to smile and close his door whenever he got into a heated phone call, and everyone in the office was happy with the solution."

Explanation of the Answer

Notice the response fits the formula perfectly.

  • It describes a challenging situation that does not make the interviewee feel angry and was resolved effectively by the interviewee.
  • The situation is explained without badmouthing anyone. The interviewee does not say he or she disliked the employer, but, instead, focuses on a situation that needed to be resolved.
  • It tells what steps the interviewee took to solve the problem.
  • And it describes the positive outcome of the interviewee's actions.

Another Sample Answer

I've posted another sample answer to this type question in response to a reader's post on the same topic. You'll find that sample question and answer here.

And for more answers to tough interview questions, take a look at this Job Interview Guide

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