Beware the ‘Tell me about your boss’ Question!

Personal Branding

Imagine for a moment that an exceptional job candidate is about thirty minutes into an important job interview. The candidate, whom we’ll call Joe, and the hiring manager seemed to have hit it off almost from the start. Joe has nailed every job-related question the hiring manager has thus far asked him. Because the hiring manager has such a pleasant personality and relaxed, friendly manner, she has put Joe completely at ease. He is absolutely certain at this point that he is a virtual “shoo-in” for the job. Then, seemingly out of the blue, the hiring manager asks him, “So, tell me about your boss.”

Suddenly, an alarm—albeit, a small alarm—goes off in Joe’s head. He hesitates answering her question for a moment because he is unsure how to answer it, or at least how to truthfully answer it. This could be a “trap,” he thinks. “How can I say anything positive about the jerk I now work for?” he asks himself. After all, his current boss is the primary reason he is looking for a new job!

The hiring manager, sensing Joe’s hesitation, quickly, and apparently with a great deal of empathy and genuine concern and understanding, adds, “Oh, you can be honest with me, Joe. Let’s face it, we’ve all had some pretty bad bosses in our time, including me. Just tell me the truth. I assure you I’ll understand.”

Whew! Joes thinks to himself, once again relaxing, for a moment there I was fearful that I might “blow it!”

“Well, all right,” Joe finally says, and then immediately begins to detail, chapter and verse, everything he feels is bad about his current boss. He brow-beats his employees. He consistently takes all the credit for work really done by those under his supervision. He is rude, boorish and abrupt, and on and on. Joe literally leaves no stone unturned when it comes to berating his current boss and describing just how truly awful he is. (This is what I refer to in “Headhunter” Hiring Secrets as“spewing venom!” something to be avoided at all costs during a job interview!) Finally, he adds, almost gratuitously, that the principal reason he is now looking for a new job is because of his current boss!

Sound the buzzer! Blow the whistle! Ring the bell! Joe is “out of the game!”

Joe did, in fact, and in every sense of the term, just “blow it!” He instantly and irretrievably branded himself as a whiner and a complainersomeone who probably can be expected to cause nothing but trouble and discontent, in the now extremely unlikely event that the hiring manager were to select him as her candidate of choice. He literally is “out of the game” at this point.

Unfair? You bet it is. Wasn’t the hiring manager just “game playing?” Again, you bet. But there is even more bad news: Today, hiring managers and the companies they represent don’t play “fair.” And, as I repeatedly point out in “Headhunter” Hiring Secrets: The Rules of the Hiring Game Have Changed . . . Forever!, hiring is indeed a “game,” a very serious game, to be sure, and one with all new rules! Either accept these facts, then learn these new rules, as well as how to effectively play by them, or you will be quickly eliminated as a viable candidate in today’s job market—just as Joe was.

Joe, of course, should have gone with his first instinct. The hiring manger (aka his “new best friend”) did indeed set a “trap” for him—one of a number of “traps” today’s hiring managers are sometimes wont to set for the unwary, unsuspecting job candidate!—and guess what? Joe rushed headlong right into that trap! As a result, Joe’s candidacy ended right then and there. He was excluded from any further consideration! (Again, as I repeatedly point out in “Headhunter” Hiring Secrets, the hiring “game” is first and foremost one of exclusion, not inclusion, as many job hunters erroneously assume! That is, hiring managers today, who are already overwhelmed with candidates, want to eliminate as many candidates as possible, as efficiently as possible, so that they can more quickly get to their final “pool” of desirable candidates and ultimately select the candidate of choice.)

So, how should Joe have answered the hiring manager’s question? As is most often the case when it comes to answering job interview questions, there is of course no one, all-encompassing, works-every-single-time answer. Here, however, is just one of several ways our recruiting firm coaches our candidates to respond to the “boss” question:

“Mr./Ms. Hiring Manager, 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.”

But, you might be thinking, this is disingenuous, this isn’t “truthful!” You are absolutely correct, at least insofar as “Joe’s” situation is concerned. 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.” If you do so, you (like Joe) 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 a.) doesn’t even know your current boss; and/or b.) 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/her company is likely to be—if you are their candidate of choice. That’s it!

Consider it very likely that you, too, will be asked the “boss” question at your next job interview. (The “boss” question is just one of the many “Gotcha!” questions we cover in “Headhunter” Hiring Secrets.) Remember, your answer to this question will brand you either as a malcontent, 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.


Skip Freeman is the author of “Headhunter” Hiring Secrets: The Rules of the Hiring Game Have Changed . . . Forever! and is the President and Chief Executive Officer of The HTW Group (Hire to Win), an Atlanta, GA, Metropolitan Area Executive Search Firm. Specializing in the placement of sales, engineering, manufacturing and R&D professionals, he has developed powerful techniques that help companies hire the best and help the best get hired.