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Advice / Job Search / Finding a Job

3 Questions That'll Help You Figure Out What Kind of Boss You Need Next

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It’s often said that people don’t leave a job, they leave their manager. But, in my experience, you don’t just accept a job either—you accept working with the person who’s going to manage you, develop you, and (ideally) help you advance in your career.

How often have you applied for a role you thought sounded perfect, but had second thoughts after you’d been interviewed by your potential manager? Perhaps you just didn’t click, or maybe you felt unconvinced that your working styles would fit together comfortably. It’s perfectly reasonable to decline or accept a role based on how you feel about the person you’re likely to work with most closely on a daily basis. But what about when you’re not getting a good or bad vibe, this person’s just coming off like any other boss?

How do you know if he or she’s the right supervisor for you? Ask yourself the following:


1. What Three Values Are Most Important to Me?

Grab a pen and paper and write down the three values most important to you. Are they honesty, hard work, respect, fun at work, personal relationships, meeting deadlines? The possible answers are almost endless, but whatever they are, spend time really thinking about which ones you hold near and dear and which ones you’d be willing to compromise. Then, ask the question below during the interview and you can see how many match up with your list.

What values do you think are most important to being successful on this team and in this role?

By finding out what values your prospective manager holds in high regard, you’ll get a pretty good idea whether your values will clash or (fingers crossed) be a match made in heaven.


2. What Do I Want From My Next Manager?

Are you looking for a boss who will bolster your ego and back you all the way, or do you want a mentor who will guide you on your path? Spend some time really thinking about that; it’s going to be crucial to your next career move.

Because if you’re looking for an equal partnership instead of a mentor, and you end up with a leader who is intent on developing you in ways you’re not excited about, that’s going to be a source of friction. In order to make your next move a great one, you’re going to have to work out which type of leader you need right now. When you have an answer for yourself that you feel comfortable with, ask this:

Are you looking for someone who can take this role on from day one, or are you looking to help develop someone into to his or her full potential at this company?

From the answer, you’ll know if he or she’s looking to really teach someone or a trusty sidekick.


3. What Motivates Me to Do My Best?

What motivates you the most? Maybe it’s the obvious one—money. Or, maybe it’s travel, personal development, a foosball tables in your office, or work-from-home flexibility. I don’t know. But you do—and you need to work out if your manager is willing and able to give that to you.

If you’re driven most when working from home, chances are a boss who expects you to sit at your desk from 9 AM to 6 PM isn’t going to be best for you. Similarly, if you like public praise, and your boss thinks you should be gratified by a brief “thank you” email, there’s going to be hurt feelings down the road. So ask this:

How do you like to recognize and reward successful employees?

If the answer is “with an annual company picnic” when you’re really holding out for company shares, you’ll know that your search for the perfect job continues.



Now that you’ve done the work, and given some serious thought to what it is that you want–or really need—from your next manager, get out there and put your questions to the test. The best boss ever is only just around the corner.