How to Avoid Working for a Boss Who Will Make You Miserable

By Rich Bond

The Wall Street Journal just ran an article on “How to Jerk-Proof a Job Search.”

I don’t like the title, but the message is a good one. If you change jobs, you want to move into a role where you can grow and have a good chance of success.

Interviewing is a two-way street – the hirer should learn about the candidate, and the candidate should learn about his/her potential boss.

It is important for candidates to be as prepared as possible for an interview. The one area in which most candidates fail is that while they are prepared to answer questions about themselves, they don’t have good questions to ask the person who is interviewing them.

One of my favorite questions for a hiring manager is, “If we were sitting here a year from now, and I found the perfect person for your role, and that individual was a total success, how would things be different?” That could spark a really good set of questions and conversation. Hiring managers who can’t define success are hard to work for. As Winston Churchill supposedly said – If you don’t have a plan to succeed, you are planning to fail.

When you’re on a job interview, it’s hard to see the forest for the trees. You’re so focused on selling yourself, you might miss the red flags about a not-so-great employer. To avoid ending up with a boss from hell, I recommend asking the tough questions after you’ve got an offer in hand. You’ve got maximum leverage during this phase, so take advantage of it!

Before Covid, my suggestion to a candidate who was “on the fence,” was to arrange a visit to the offices where s/he would be working to meet some of the other employees and get a sense of what it would be like to work there. This visit usually made the candidate enthusiastic about the company or resulted in turning the job down.

If the job is virtual, it is harder. You might ask to observe a regular meeting.

What are your opinions? What have you experienced?



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