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How to Interview Your Prospective Boss Before You Accept a New Role

How to Interview Your Prospective Boss Before You Accept a New Role

You’ve heard the adage:

People don’t quit their job, they quit their boss.

If you are looking for a new career opportunity, don’t miss out on the chance to interview your prospective boss to determine if they are a best fit for you. Your success and satisfaction are aligned with the leadership to whom you report, so remember that you are interviewing your future boss as much as they are interviewing you.

I practice what I preach in this realm and have interviewed my prospective bosses over the last decade before I accepted new roles. These conversations set me up for success and gave me an eyes-wide-open look at the leaders I chose to work alongside.

[Related: Good Communication Makes for Great Business]

Timing is essential.

Depending on the role and the organization, you may not even set eyes on your prospective boss until you are a finalist for the role you seek. Keep your eyes and ears open to sleuth out company culture and how people treat each other during the hiring process.

Are they smiling in the interview - even on Zoom? Do they look and act enthusiastic and engaged? How are they treating each other as colleagues?

If on onsite interview is part of the experience – look around and see how people are behaving. What’s the mood of the team? Is it a sea of headphone clad professionals in cubicles, or are people engaging with each other?

No judgment on either scenario, but these are clues that will help you decide if this is an environment where you can do your best work.

The interview ask.

It’s imperative to come to every interview with questions you can ask the team. But interviewing your boss requires a separate and private conversation. When you become a finalist, it’s time to ask the hiring manager to schedule a separate 30-minute conversation with you and your prospective boss.

Explain that this is your opportunity to get to know the leader better and determine if the hire is a mutually beneficial fit. A one-on-one conversation will allow you to get to know each other better. Avoid a lunch meeting for this interview, since it can be distracting and does not allow for a private and focused conversation.

I encourage you as the candidate to take copious notes during this conversation, so you can factor the answers into your decision-making process if you are ultimately extended an offer.

[Related: The Best Job Search Strategy: Job Seek Like a CEO]

Interview question ideas for your boss-to-be.

Remember, the spirit of this conversation with your boss-to-be is to learn more about them and discuss what you value in a leader and a work environment to learn if you are simpatico. Here is my long list of favorite questions, plus a few from SHRM, which you can customize to meet your specific needs, and add your own.

You will decide which questions are most relevant to you. Keep it conversational and honor the 30-minute meeting request. If they extend the conversation – this is bonus time with your prospective boss, and a very good sign.

  1. How do you prefer to communicate?
  2. What’s the best way to ask for your input and feedback?
  3. How do you give constructive feedback? Do you welcome it from others?
  4. What are the biggest strengths and challenges of the team and our goals?
  5. What can I do to support our team and add value to the organization?
  6. What would you add to, or subtract from, the current team in order to strengthen performance or productivity?
  7. With whom should I meet outside of the team to pursue my due diligence about this role?
  8. What is the team/company culture you wish to develop and nurture?
  9. Do I have your permission to take innovative risks, fail-forward, and showcase resilience when things don’t work out?
  10. I value a culture with psychological safety (when a team or organizational climate is characterized by interpersonal trust and a climate of respect, where one feels free to collaborate and feels safe taking risks or making mistakes, which ultimately enables the team to implement rapid innovation). Does psychological safety exist on this team? 
  11. What does success look like to you?
  12. What is a misconception people have about you, and why?
  13. How do you groom and develop direct reports for advancement?
  14. How do you re-charge and tend to your self-care?
  15. What else do I need to know about you that I have not asked?

Decision time.

After you interview your prospective boss, you must take the time to reflect on whether they are a good fit for your work style and your future career goals. We spend many waking hours at work and our relationship with our direct leader impacts our personal and professional satisfaction, productivity, and advancement.

Be a bold, professional, and savvy candidate and ask your future boss for a brief conversation, so you can interview them and determine if this is a professional match you want to pursue. I know from experience that it’s 30 minutes well spent!

[Related: Three Common Negotiation Obstacles and How to Overcome Them]


Caroline Dowd-Higgins authored the book "This Is Not the Career I Ordered" and maintains the career reinvention blog of the same name. She is Vice President of Career Coaching and Employer Connections for the Ivy Tech Community College system and contributes to, Thrive Global, Ellevate NetworkMedium, and The Chronicle newspaper in Indiana. Her online video series about career & life empowerment for women is on YouTube. She hosts the three-time award winning podcast, Your Working Life, on iTunesSpotify, and SoundCloud. Follow her on Facebook, LinkedIn, Google+, and Twitter. Her TEDxWOMEN talk about reframing failure and defining success on your own terms is available on YouTube.

Have more questions? Follow up with the expert herself.


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