I wrote a post recently about how a great boss is a career accelerator and why it’s worth evaluating a new boss as critically as we evaluate a new role. The post sparked with people, and the most common response I heard was: “But how do I do that?”

😮 uh-oh.

I wish I had a simple answer. I don’t. But I’ll try. Just keep in mind, this is not a complete list, only a few things I’ve started to look for in my own search for an amazing boss.

Does this person make time for you? I still remember emailing my would-be-boss from my last job and getting a response within three minutes. He liked my email, skimmed through my resume, and immediately saw that I was a good fit for the role. So he made time for me, and that made a big impression. You shouldn’t always expect a response time of 3 minutes :) But as you move through the interview process, watch for where you fall on your future-boss’s priority list. Do they show up on time for the interview? Do they answer follow-up questions promptly and thoroughly?

Can they teach you something? A great boss isn’t defined by likability (though that is nice), but they must be someone you can learn from. Particularly early in your career, you’ll likely have 1 or 2 skills that you know you want to focus on developing -- find a boss who is wonderful at those things and will take the time to teach you as well. If you want to be the best, learn from the best.

Do they have a track record of accelerating careers? A responsible hiring manager will always do reference-checks, and you should do a version of the same. Ask your would-be-boss what their best manager to direct report relationship was:

    • What was that person’s name?
    • Are they still with the company?
    • What would that person say about working with them?

Then hop on LinkedIn and find out where that person went. Good signs are when a boss has direct reports that move on to amazing companies and bigger roles (either inside or outside the company).

What is their management style? This is the easiest way to check for compatibility with your boss and almost nobody does it. Ask questions like:

    • How often do you meet with your direct reports?
    • Tell me about the best manager you’ve ever worked for?
    • What would your direct reports say about working with you?
    • What would they say your strengths and weaknesses are?
    • How do you give feedback to direct reports?

These questions likely look familiar. They are very common questions that hiring managers pose to interviewees. They show a sense of self-awareness, and an ability to understand your own working style. But as the interviewee, they can work for you too!

Do you trust this person? This last point is a little more advanced and I would recommend leaving it for the later stages of the interview process. But at some point you want to make sure that the person you’ll be working with is someone that you trust (I’ve written before about how important trust is at work), and the only way to do that is to ask an uncomfortable question that requires trust to get an answer.

    • It could be something about you: “I know that my lack of experience in X could be an issue. Do you see that as being a potential problem?”
    • It could be something about the role: “I get the sense that there is a lot of confusion about goals for this role. Can you help me understand where this confusion is coming from?
    • It could be something about your boss, the company, or your team.

The only rule here is that asking the question should make you feel a little uncomfortable. Your boss is someone that you’ll be talking to about failures, successes, and family illnesses. Now is the time to make sure they’re the kind of person willing to have honest conversations with you...even if those conversations are a little awkward.

It’s not always possible to carefully evaluate a great boss. Sometimes we just need a job ASAP, sometimes the hiring processes are so archaic we don’t even get to meet our future manager. But when you have the opportunity -- take it. Don’t miss the chance to thoughtfully seek out an amazing manager.

It’s worth it.


Originally published Feb 1, 2018 9:00:00 AM, updated January 19 2023