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Interview Tips and Questions

One of the interview tips and questions you won't relish answering is:

Describe the most difficult boss you ever worked for and how you dealt with them.

This question is very similar to the behavioral interview question: What qualities do you look for in a boss? This is the flip side of that coin.

Now they are asking you to describe your boss from Hell.

The word, difficult, is the operative word here. Your perception of difficult may be completely different from mine.

True Story: Early in my career I worked for an extremely demanding, autocratic boss who would erupt into fits of rage if something went wrong.

He intimidated and upset a lot of people; however, I got along well with this manager despite our opposite management styles.

As I look back on this experience, I realized that the reason we got along is because I did my job well by solving problems and getting results. He didn't have many occasions to chastise me, or my department.

I also discovered that when I looked beyond his tirades and tantrums, he was really trying to do the right thing and was honest.

For this reason, I didn't take his behavior personally, and could stand up to him without feeling intimidated. We sure had some lively debates though!

Most of all, I grew from my association with him...even though I would have much preferred to work for someone else. A mutual respect developed between us that lasts to this day.

What kind of an impact do you think this story would make in an interview?

Here are some positives my interviewers might be thinking about me:

  • He can work with demanding managers
  • His management style is participative...which is what most employers want
  • He can stand up to a tough boss
  • He learned and grew from this experience
  • He is self confident, solves problems, and gets results

Maybe the reason you are being asked this question is because this employer knows you will be facing one or more of the following challenges:

  • Your manager is autocratic and few people can work for him/her.
  • Your overbearing manager is nearing retirement and they see you as his/her replacement.
  • Expectations are high, and you will be held strictly accountable. Can you handle the pressure?
  • Your boss may be a good person, but a micro-manager.

You may be asking yourself, why would I even want this job if I may have to work for a tough boss? Here are a few possibilities:

  • This is a turnaround division of a large stable company with an overall good culture and reputation. This could be fertile ground for you to make a difference and advance your career quickly.
  • This could be a start up operation of a great company that is experiencing short term headaches and problems.
  • This employer may have hired poor leaders in the past and now wants to infuse strong leadership into their organization.
  • This could be a stepping stone along your career path and you need specific skills and experience that this job provides.

Interview Tips and Questions: Usually at some point during your interview you will be asked, Do you have any questions for us?

A good question to ask your future boss is: What is your management style like?

Tough minded, hard charging managers won't be bashful about telling you how they operate. You will quickly get a flavor of what to expect.

Pearl of Wisdom: A job interview is a 2 way street. By asking a few tactful questions, you will gain some keen insights about a company's problems, culture, and expectations. Trust you instincts.

Interview Tips and Questions: What if you never worked for a difficult boss?

This certainly could be the case if you are early in your career. If you are in mid-career, maybe you've been lucky so far and all your bosses have been angels.

If so, just tell your interviewers that apparently the heavens have smiled down warmly upon you.

However, if you are 15-20 years into your career, and you lead your interviewers to believe that everything has been peaches and cream with all of your bosses, they're going to know you're lying.

Ever hear of the 80/20 rule?

In this case, 20% of your managers should have been outstanding, 60% average, and 20% lousy.

So, with 80% of your managers average to below average, someone in the bunch surely has given you a few headaches along the way.

Interview Tips and Questions Final Thought

Don't be tempted to weasel out of answering this situational interview question by saying all your bosses were just G-R-e-a-t!

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