How To Hire Your Boss

Illustration by Katerina Limpitsouni

Joe recently landed his dream job. Smart team, cool company, great pay — he was excited!

Two months later, Joe got fired. When I asked why, Joe said he had altercations with his boss.

His interviews went great. Then, the relationship deteriorated.

Communication broke, fights started. Finally, they couldn’t mend things anymore and Joe had to leave.

Joe was upset, here’s what he told me:

“I only chatted with my boss for one hour before getting the job. She then became one of the most central people in my life.
How crazy is that? Next time, I’ll hire my boss.”

Joe is right.

When changing jobs, you should hire your boss.

Most companies ask top performers to become bosses, hoping they will rock.

The reality is that not all top professionals become top bosses.

Even great bosses need years to hone their skills through practice.

Here are three thoughts on how to hire your boss:


1) Mentorship 🧞‍

Learning experiences should be one of the top reasons why you are joining the company. Studying with exceptional leaders matters more than pay.

Will your boss be the mentor you need in the current chapter of your professional life?

During your interview, ask questions you care about, not the ones that make you sound smart.

For instance: “What is your favorite part about managing a team?” and “How will you evaluate my performance?”

If asking candid questions makes your boss feel uncomfortable, they aren’t the best mentor for you.


2) Personal Improvement 😅

How does your boss see the company? Anytime I hear “We’re a family,” I get scared.

Companies aren’t families, they are closer to professional teams. All employees have previous teams and will have future teams.

Ask your boss about the skills she intends to teach you. Tell her what you wish to learn.

Don’t work for a boss who is uncomfortable with the idea that you will work elsewhere in the future or doesn’t support your personal growth.

A boss who is excited to work with you as a person will be supportive when you eventually decide to leave their team.


3) Compatibility

Getting to know your boss will take time. Yet you can get a feeling for the workplace and your colleagues’ personalities straight away.

When the interview process becomes serious, continue emailing questions to your boss. Also, ask to speak with your future peers.

Find out if the team operating model feels compatible for you.

Collocated or Remote? Hands-on or hands-off management? No-meeting Wednesdays or daily standup? How often do they do 1:1s?

Ask what success looks like to your boss/team. Ask about folks who recently departed or have gotten promoted and why. Ask what they expect your contribution to be.

Don’t work for someone who feels upset when questioned about their decision process.


This may sound like a lot of work.

Remember, most of us only chat with our boss for one hour before getting the job. Then, your boss becomes one of the most influential people in your life.

You are trading the one thing you can’t get more of: your time. Make sure it is appreciated!

Don’t work for a boss who doesn’t welcome candid questions, personal ambition or doesn’t want to be challenged.


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