One of the things I’ve noticed about working with job seekers, is that oftentimes the most important thing they’re looking for in their next job isn’t a specific title or organization, but a great team, and in particular, a great boss.      

I often hear words and phrases like ‘trustworthy’, ‘interested in coaching and helping me grow’, ‘kind and warm’ or ‘inspiring leader’ to describe what they want in a future boss and mentor.

But how do you find those great bosses to work for? It can be really tricky, and sometimes it feels like you’re looking for a needle in a haystack. And let’s not forget that someone who is a great manager for you might be a very challenging boss for someone else – therefore, finding a good boss means finding a good boss for you.

So what actions can you take during your job search to really figure out if a potential boss will be a great manager for you?

Here are three specific strategies to help you find your next boss:

1.     Take time to reflect on what has worked for you in the past and get specific.

Think about the bosses you’ve liked, and those you’ve had difficult relationships with. What are the specific actions they took when working with you? How did you solicit meaningful feedback from them? What types of communication styles worked for you and which didn’t?                 

Here are some specific questions to help unpack what works for you with a boss:

• Do you prefer working for people who have a more laid-back approach and check in with you less frequently, or do you appreciate a more hands-on approach with daily or weekly check ins?

• How do you like to communicate and get info from your boss? By email, phone, face-to-face meetings, or does it depend? (Some people like everything in writing so they can refer to it easily while would find that approach overwhelming or excessive.)

• How would you want your manager to start a project? Would you like them to take their time and map out all the steps or jump into action quickly?

• When making decisions, have you liked managers who love to pour over data and information or have you enjoyed managers who go with their gut?

• What qualities and characteristics have signaled that there was trust between you and your boss in the past?

After you’ve reflected on the above, you’ll know what specific answers to look for from potential managers to understand their style and see if it will be a good fit. If you feel strongly about any of the above examples, those are the specific qualities you might want to probe deeper with during interviews.

2.     Ask really good questions. 

The above reflection should give you a pretty good list of questions to ask in order to evaluate how your working styles might mesh or clash.

Here are some other questions that can help you get a better picture of what your working relationship might look like:

Interaction and Engagement: These questions will help you anticipate how much interaction you might have with your boss and how much ownership you might have in setting your priorities and career goals:

• How often do you like to meet with your direct reports?

• How long are those meetings?

• Who sets the agenda?

• What do we usually discuss in our check in’s?

• Are there distinctions between meetings that are for check in’s on projects vs. bigger conversations around performance and development?

Investment in Your Development: These questions will help you understand your potential boss's track record of promoting or helping their team members achieve their career goals:

• Tell me about the people you’ve managed before – where are they now?

• What do you enjoy most about managing this team?

• What are your career goals? Where do you see yourself going over your career?

If progressing into a role like your future boss’s is something you might be interested in, it might be really good to know what your potential managers’ career plans might be to see what upward career growth might be possible.    

Communication Style and Feedback: These questions will help you understand how they communicate and how you might expect to get feedback:

• How would I know that I’m doing a good job and that you’re pleased with my work? How would I know I’m not meeting the mark? (If getting positive feedback is important for you, and you appreciate constructive feedback to continually improve, finding out how they give feedback will be super important!)

• How would I get the best of you and worst of you as my manager?

• What three adjectives would you use to describe your management style?

• What keeps you up at night? This question can be a great clue for what the biggest headache and pain point might be for your future boss. (Bonus point: If you can share with them in the interview how you can help ease that pain point, you’ll stand out.)

Keep in mind some of these might feel more appropriate to ask farther in the interview process or after you’ve gotten an offer.

3.     Get data from team members or past people your future manager has managed.

There’s nothing better than getting intel about a potential manager from someone who’s actually been managed by that person.

Here are a few good questions to ask other team members or past people they’ve managed before: 

• What have you enjoyed about having X as your manager?

• What has been challenging about having X as a manager?

• What do you wish you had known about working with them before you started?

Lastly, if you’ve got concerns or are seeing potential red flags, it may be helpful to ask some behavioral questions -- just like the kind you get in an interview (like: Tell me about a time when… or What would you do if…). You can pose similar questions to the potential manager, or to those who have worked with them before, to get a better sense as to how a situation might play out.

Start by thinking about what type of situation triggers you and probe with a behavioral question on that situation to get a sense of how things might play out. For example, let’s say one of your biggest triggers is when deadlines change and aren’t communicated. You might ask, “Let’s say a deadline gets changed last minute on a project. How do you usually communicate these changes?” or “Could you give me an example of a deadline that got changed last minute on a project and how that was relayed to the team?”

It can be tricky to be positive and easy going in the interview process, but also get underneath and really know what it would be like to work for someone.

These reflections and questions will set you up to know what you’re getting into before you start your new role, and will help you identify the managers that will most support you to be successful in a new position. Try them out and let us know what you think!