While the focus of CCCC is with the CEO and top executives moving forward in their own enterprise, the company’s coaching sometimes extends to executives seeking to make a career change and thus, undergoing the interview process.  As we prepare the individual for that interview, we find they are thrust into an environment that is full of embarrassing questions.  Here, then, is how we think they should be addressed.

  1. The Principle

It is our opinion that embarrassing questions do not belong in the job interview.  For it is nothing less than bullying by someone in an advantageous position. It is not respectful.  However, the world is anything but ideal.  Many people who have the privilege of interviewing have no idea of how to do it properly. (See a separate paper by CCCC on how to interview.)

So, accepting that it is anything but a perfect world, how should you respond to an off-putting question during a job interview?  How do you avoid feeling tongue-tied?  How do you not look like a fool?

Follow these principles:

a) Most people do not know how to interview, so do not be surprised by behavior that is less than professional.

b) When hit by an embarrassing question, buy time by responding with one of the following:

  • Would you re-phrase that question, please?
  • Did I understand you to ask……? (re-state the question in your own words)
  • How do other people respond to that question?

This buying of time allows you to collect yourself emotionally.  It also allows you precious minutes to think of how you will form your response.  Thirdly, your comment may cause the interviewer to withdraw the question realizing that it might be inappropriate.

c) In those few minutes of time, try to ascertain why that question is being asked. Then respond to that reason.  “If you are asking if I have enough stamina, then I should tell you about…..”

If you have made the wrong assumption, the interviewer will tell you and get you on the right track – which you may find is not embarrassing at all.  If you have made the right assumption, you have challenged the interviewer to get onto a level playing field; the interviewer will realize the ‘little trick’ question will not work on you.  Likely, you will be treated with more respect thereafter.

d) Keep your answers natural. There is nothing worse than a canned response.  To keep them natural is done by preparing yourself beforehand, so that you are not caught by surprise.  Beforehand you can create an honest answer that you don’t have to memorize, because you have thought it out and have made it really you.

  1. Embarrassing Questions


Let us use a selection of favorite questions and suggest how you should reply.

a) Have you ever been fired from a job?

First, think of why this question is being asked.  It could be that the interviewer believes that anyone who has been fired is not an exemplary employee. Or just the opposite – anyone worth their salt will have stood up for their way of doing things despite the superior’s view and thus be sent on their way.  Or the interviewer is simply trying to see how you react to a curve ball.

The reality:  90% of people who leave jobs, do so because of a poor relationship with their superior.  So an unworkable job situation is a very common phenomenon.  If Sam decides to quit his job, it is no big deal.  However if Sam is fired, even an hour before he was about to quit, there is a significant social negative attitude attached to the event.  Quitting or getting fired are opposite sides of the same coin.  The job no longer fits the employee; it’s just a matter of who acts first – the employee or the employer.

Thus it is no disgrace to be fired.

The response:  “Yes, but it was the best thing that ever happened to me.  I went onto a new challenge that was much better for me (or I now have the opportunity to get into an area where I can excel).

You show you are not flustered.

You put the event in the right perspective.

You put a positive spin on it instead of a negative one.

b) Did you ever have to fire a friend? What happened?

 My glib, but true, answer is: “Yes, and she divorced me right after that.”

Assuming you don’t have that one, you probably should re-phase the question:  “If you are asking if I would have the discipline to fire a misfit person in the company, I can assure I would do, and have done, whatever prudence in the job dictates.

c) Why should I hire you?

 Before applying for the job, decide on the three most important characteristics that you bring to this job, three that match the requirements of the job.  Determine no more than three because the reality is that (a) you can’t remember more than three (b) most interviewers’ minds can’t process more than three, and (c) any more than three waters down the importance of those three.  Then spit out these three reasons:

“Because I bring proven determination, have 10 years experience with voice over IP technology and have successfully managed a team of a dozen engineers.”

 d) What do you really want out of life?

 “Good God, who knows?  Wine, women, song and gold.” might be your first reaction.

Reality: People want to feel valued, that what they do in life, personal or work, makes a positive contribution.  They want to feel good about themselves.  People want to progress from one level to the next level or challenge.

Craft your response around those ideas.

 e) What do you really want from me?

 “Holy smokes man – a job!  Why do you think I’m here?” is not a reasonable answer.

Perhaps it is not wise to ask the person to re-phrase this question.

The Reality: You expect this person to be a conduit between you and your skills and the job.  That is, you expect to find if you fit the job and if the job fits you.  You therefore expect the interviewer to help you ascertain the degree of match.  Choose your own words.

f) What are your weaknesses?

 The reality: None of us is given a full deck of cards.  We have our strengths but we also have our weaknesses.  The weaknesses complement our strengths.  For example an impatient person has the weakness of a lack of patience.  But it is this lack of patience that makes the person results-oriented, driven and hard-working.  However we can’t expect the interviewer to understand this.

Our recommendation is that you focus on weaknesses that are not fixable, so you don’t have to plead about how you are going to do better – which the interviewer would never believe anyway.

And, then, just add one more negative to your evaluation form.

Let us assume that your weakness is accounting – you hate doing financial spreadsheets and cash flows.  Your response might be:

“I hate accounting.  I stay as far away from it as I can.  If there is a need, then I bring in the right person to take care of that for me.  This job doesn’t have a lot of accounting does it?”

 Naturally, if this job did have a lot of accounting, you would simply excuse yourself from that one.  More likely, the job has miniscule accounting and most people in the company also leave it to others who are more skilled in the area.

g) Describe a failure.

While CCCC has several papers on the importance of failure, this is not the place to trot them out.  The reality: It is only through failure that learning gets impressed on us. That is why we must repeat the mistakes of previous generations – to learn ourselves through our mistakes.

Assuming the interviewer doesn’t grasp this point, and even if wisdom does prevail, you want to show that you do make mistakes and that you learn from them.

Think in advance of a fairly big mistake and what was learned from it.  Bring that forward when this question is asked.  Avoid discussing a small mistake; it looks like you are afraid to be honest.

  1. Conclusion

Calm honest answers in the face of embarrassing questions are your best weapon to move from the interview to the job.  It can only be done if you prepare in advance.  And those unexpected questions, you could not prepare for, require you to buy time and to challenge the interviewer.

Bill Caswell