What was your favorite position, and what role did your boss play in making it so unique?

Why Ask This Question?

Much like the greatest strength question, this query invites the interviewee to reflect on positive and comfortable emotions. It also prepares the stage for the related question to follow (which is much harder to address), ''What was your least favorite position or company?'' Still, there are telling clues in the individual's response, so let's look for the salient issues.

Analyzing the Response

Human resources professionals and executive recruiters will attest to how warm and cozy this query generally makes candidates feel. A candidate's body language often will totally relax, and a warm smile will appear. Their responses, however, could indeed knock them out of consideration for a job when they sell a love for a particular aspect of a past position that you are not offering.

Red Flags

Take the case of a marketing representative named Joan. When the question about favorite jobs came her way, she mistakenly mentioned a past job that was extremely creative and got her out of the office a few hours a week. She had worked for an international firm that offered the opportunity to entertain foreign dignitaries, and she had been responsible for giving tours of the company's solar energy plant.

Granted, that may be why that particular job stood out in Joan's memory. However, because the job she was applying for didn't offer those non-traditional perks, she ended up selling her love of tasks that she wouldn't be handling on the new job. She consequently weakened her case because the company felt that she was overqualified—in other words, the organization couldn't offer her the glamour and variety she was accustomed to and felt she wouldn't be stimulated in its nine-to-five environment.

Note as well that statistically a majority of people leave their jobs because of personality conflicts with their boss. No matter how well the company fares, once that key interpersonal relationship sours, there's very little opportunity left for a subordinate to assume greater responsibilities, earn significantly more money, or remain part of the unit's succession plan. Therefore, you want to connect what role a boss played in making a job a favorite position, just as you want to tie in the supervisor's role in making a job a least favorite position.

What was your least favorite position? What role did your boss play in your career at that point?

Why Ask This Question?

The body language changes very quickly when candidates are presented with an invitation to criticize or censure a former boss or company. After all, this query baits individuals to complain about the people to whom they should be most loyal. The ideal candidate response avoids subjective, personal interpretations that force respondents to defend their past actions. Instead, a solid response will address objective issues that place an impersonal distance between the candidates and the external factors that interfered with their ability to reach their personal best. In short, look for job candidates' abilities to objectively evaluate a situation rather than irrationally react to it.

Analyzing the Response

Red Flags

Little needs to be said regarding candidates who shoot down past bosses. These people automatically place themselves in a victim posture by assigning blame to others. They also show little interviewing sophistication because they fail to realize that you are taking their answers with a grain of salt: After all, most managers can relate to being the brunt of a subordinate's criticism. Why, therefore, should candidates expect you to choose sides when only one side of a complaint is being described? Besides, the candidate's former boss isn't even there to present the other side of the story, so why should you be forced to show empathy to one party and not the other? No doubt about it—talking poorly about a past employer is one of the worst things candidates can do in the interviewing process.

Good Answers. In discussing a least favorite position and the boss's role in making it so, candidates will usually address the interpersonal challenges they had with bosses who stifled their career growth. Here's how certain positive responses might sound:

''What I disliked most about my former company is the fact that it offered very little risk and reward. It was a very mature company with exceptionally long staff tenure. I respect any company that can build loyalty and longevity in the ranks, but my boss, the CEO, was preparing to retire, and we senior managers were not expected to 'step outside of the box,' so to speak, when it came to taking risks. That wasn't the type of corporate culture that I wanted.'' or

''My least favorite position is unfortunately the position I now hold. My boss, the chief operating officer, inadequately prepared for a change in the business environment. The firm made hay while the sun was shining when interest rates were their lowest in thirty years. However, he put all the company's eggs in the refinance basket and developed few contingency plans for the inevitable increase in rates. That kind of quarterly profit mentality went against my better business judgment.''


If I had to critique a past employer's performance, I would have to say that working for Jay Panico, the senior vice president of sales at XYZ Company, had the most challenges. We worked very well together personally, but Jay needed to be much more proactive in terms of anticipating the workload. He prided himself on putting out fires. My style, conversely, was to forecast potential problems before they arose. It got very tiring after a while and took the fun out of coming to work every day.''


''My least favorite boss was probably Denise Spaulding because she was so cynical. She provided our team of first-line supervisors with little structure and direction in our day. Her door was closed most of the time, and she was openly uncomfortable hearing about our problem issues and concerns. That made relying on her as a resource fairly impractical. Worst of all, she spoke poorly about the firm often and was renowned for causing an overactive grapevine.''

These solid responses share objective evaluations that place no blame on anyone while gently probing realistic organizational or individual weaknesses.

Where do you see yourself in five years?

Why Ask This Question?

This question is a known showstopper because it triggers a candidate's ''wishful response'' mechanism. You'll hear about people who want to be retired on a desert isle. You'll see flower stand owners in the making. Those who want your job five years from now might even make you a little nervous! And what about those respondents who say that five years from now they want to be holding the same job they're applying for today? So much for healthy career ambition!

If it seems as if anything and everything candidates say will weigh against them, you're realizing the pitfalls of this question. The fact that candidates simply seem to throw caution to the wind might provide some interesting insights that might not otherwise surface during your meeting. After all, if the candidate's five-year goals have absolutely nothing to do with the job you're offering, how could you build long-term plans around the person?

Analyzing the Response

First of all, when candidates respond with a far-out answer like retiring to Tahiti or opening a bowling alley, note down their responses. Then bring them back to reality by requesting that they tie their responses in to the business world and your industry. Second, when candidates name a title other than the one they are applying for (i.e., speaking prematurely about promotional opportunities), question: ''How long would you expect to have to work in our company to realize that goal? What skills and experiences would you have to master in order to make that five-year dream a reality?''

Good Answers. A realistic response will typically show that a candidate's long-term goal will be attainable only after three or four years. Getting the prospective new hire to commit to that number of years sets up your long-term expectations and minimizes the chances of premature turnover due to a lack of sufficient growth opportunities. It's not uncommon, after all, to see new hires leave a company after six short months and decry the lack of promotional opportunities at the firm.

In addition, a smart response will avoid naming job titles other than the position the candidate is applying for. The proper candidate response will, instead, place more emphasis on the assumption of broadened responsibilities at the current position. So instead of listening to a staff accountant address her desire to attain her first divisional controllership with your Fortune 500 organization, you'll hear more about the candidate's desire to assume broader duties as a staff accountant that allow her to make a positive impact on your department:

''Ms. Employer, I believe I can make the greatest contribution to your company by focusing on my general staff accounting skills. That's where my total focus lies. Where it leads me in five years, I hope you'll eventually tell me. But I want you to know that I'll be open to adding value to your organization in whatever way you see fit.''

Voila—a balanced, logical, and realistic self-assessment that addresses your organization's needs and that person's ability to provide solutions to those needs.

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