Tell Me About Your Best Boss and Your Worst Boss

By Fran Sullivanbest worst boss

There you are, sitting across from the recruiter who is interviewing you for your dream job, and it is going great! You have developed camaraderie with your interviewer, and you are confident in your answers.

Then comes the seemingly softball question, “Tell me about your best and your worst boss.” You relax and prepare to get cozy with your new confidant, but wait … in fact STOP right there. In a job interview, there are no softball questions. Everything you are asked in an interview has a purpose, so think carefully before you speak.

The first part of that question is easy to answer.

We have all had bosses who seemingly walk on water. Those great leaders inspire us to do our best work. They create an environment that makes it a pleasure to come to work. They mentor and support us. It’s easy to sing their praises, but even seemingly easy questions like this one are opportunities to promote ourselves.

Advises Peggy McKee, CEO of Career Confidential, in her blog, “A great answer to the question, ‘Who was your best boss?’ sounds something like, ‘I’ve been so lucky to have great bosses from whom I learned a lot. They all have had some characteristic or habit or knowledge that I’ve been able to learn so much from.’ Then, you can say something you learned from one boss in particular that touches directly on your fit for this job: maybe it’s a skill or a habit or something that makes you extremely good at what you do.”

The flip side of that question, “Who was your worst boss?” is trickier to answer, and the right response is critical. Of recruiters surveyed, 49 percent said that bad mouthing a boss is the kiss of death for any job seeker. Although the impulse to vent, describing your boss as the spawn of Satan, is strong, now is the time to exercise self-control. You may suspect your boss has horns and bays at the full moon. Just don’t share those views with the recruiter.

“Keep in mind, however, that a job interview is not the time or the place to ‘unburden yourself’ or to ‘hang out the dirty laundry,’” says Skip Freeman, author and CEO of The HTW Group, an executive search firm. “If you do so, you will immediately be branded as essentially a malcontent, a complainer, and you will therefore be eliminated from further consideration!

“Also, remember this: the hiring manager doesn’t even know your current boss; and/or could not care less about how good or bad of a boss he or she is! So why even introduce the topic?! What the hiring manager is interested in learning from your answer to the boss question is what your attitude toward potential bosses at his or her company is likely to be, if you are their candidate of choice. That’s it!”

Freeman suggests a better answer is the following, “I’ve always been able to get along professionally with all my bosses, including my current boss. Every work situation requires that you get along with a wide variety of people, of course, from your boss to your co-workers to people who report to you. Sometimes, you have to share ideas and sometimes you simply have to agree to disagree. The most important thing is, when you leave the conversation, you need to be ‘on task’ and ensure that what you’re doing is indeed meeting the company goals and objectives.”

The chance of being asked the “boss” question in your job interviews is very likely. How you answer can determine whether you are the successful candidate. Prepare your answers carefully in advance.

Advises Freeman, “Remember, your answer to this question will brand you either as a malcontent, a complainer, someone a hiring manager very likely will ‘pass’ on; or, as a candidate who clearly prizes and exhibits a high degree of professionalism, as a candidate who can be expected to put the success of the company ahead of any personal feelings or latent animosity.”



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