Job Search Tip of the Week #19 (2018)


How to Ace Your First-Round (or Really, Just About Any) Interview

Think Like an Interviewer – Q13

“Tell me about the worst boss you ever had.”

If you get hit with this common interview question, slow and proceed with caution. You may instinctively be tempted to open with an amusing anecdote about a former employer from hell, but don’t. You’re not at happy hour with your buddies! While you may think you’re bonding with your interviewer over laidback small talk, what your interviewer thinks is that you’re a Negative Nancy who may not work well under authority or with others.

The way this question’s worded is bait for bashing a former boss. Don’t fall for it! When you talk negatively, your prospective employer will assume you’ll talk about him or her in the same manner down the line whenever things don’t go your way – and that’s a reason not to hire you.

Research suggests that the number one reason why people stay – or quit – their jobs is their relationship with their boss. That’s why the best way to approach this interview question is to use it as your opportunity to determine if you’re a good match for the company’s culture: What have you learned from all your previous bosses? What management style works for you? What kind of manager would you be? How do you address and resolve conflict?

For example: “I’ve had all types of bosses, and some were better than others at managing and communicating with me. I’ve learned that I work best with authoritative and participative management styles, I do my best work when I can operate autonomously and collaboratively as I see fit; have input into how to accomplish end goals; and get detailed, constructive feedback from my supervisor. The ‘worst’ boss I had tended to adopt more of a directive approach. We realized that we could usually prevent conflict by making an extra effort early on to clarify expectations and being open to discussing alternative ways to do the same thing. He was one of the most technically competent bosses I ever had, and from him I learned how to better balance creativity and efficiency.”

This answer works because it’s honest but stays – and ends – positive, and is vague yet descriptive (details your “worst” boss without naming names). Also, focusing on one flaw (the tendency to micromanage) or a situation that relates to how your work style and your boss’ leadership approach didn’t mesh, prevents you from venting about all the reasons you hated your old boss. In fact, using the “PS CAR” technique frames the perfect response to this question: talk about the people (your former boss and you) involved in a particular situation (for example, you disagreed about which custom product feature to develop and release first), what caused the situation to arise (diverging expectations due to a mismatch in work and leadership styles), what actions you took to address the conflict (for example, sat down and discussed how to work better together), and what the result was (what happened moving forward, what you learned about working with different management styles, etc.).

Remember, badmouthing during an interview looks badly on you, not them. Instead, when describing your former boss or coworkers, show that you’re a better person for the experiences – no matter how bad they were.

Sound Off: Who’s the worst boss you ever had, and why?

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