Interviewing the Boss: 12 Intelligent Questions to Ask to Politely Assess Your Next Manager

​When it comes to hiring new department heads and team supervisors, companies typically opt for one of two approaches: Senior leadership either hires an external candidate without team feedback or invites staff members to meet with finalists and share input. Lower-level staff aren't typically asked whether the candidate should be hired, since that authority rests with the senior leadership team, but their feedback is often sought as an important data point and to gain group consensus and acceptance.

When asked to participate in either a group or individual meeting with someone who's under consideration for the role of your next boss, how you approach the interview will make a lasting first impression on the candidate and provide your senior leadership team with insight into your people-discernment abilities. How can you delicately and respectfully glean important information about the individual's leadership, communication and team-building styles? How do you go about asking questions that will help you come to an informed decision about what working with this individual is like in order to prepare your recommendation to your organization's senior leadership team? 

"One thing's for sure," acknowledged Claudia Schwartz, director of the HR Leadership Program at the University of California, San Diego. "[Interviewing your potential boss] never really feels like a natural task because it's awkward. But don't overlook the possibility of gaining critical insight into your next boss's style and values while providing critical feedback to your senior management team. It's a great opportunity to win on both levels, and you should appreciate your organization's willingness to invite your participation."

Opening-Question Salvos

Much will depend, of course, on whether you're meeting with the potential boss one-on-one or in a group. "First-level questions may take on a different tone and feel when being asked as part of a team interview rather than in a one-on-one situation, but give ample thought in advance to the questions you plan on asking," Schwartz counseled. "Openers tend to be softballs lobbed across the plate in an attempt to get to know finalist candidates more personally, especially if they end up becoming your next supervisor, but they certainly set the tenor and tone of the meeting." Following are some group openers that may make candidates feel at home but also let them know you've prepared adequately for this meeting and have a well-thought-out strategy for selecting candidates for this role:

1. Sally, I know it's a bit awkward for us to interview our future boss, but I appreciate that our organization encourages us to do so as a team. Is this something you've done at organizations where you've worked in the past, and have you sat in our shoes in a similar situation? If so, how did you approach it? 

2. If you don't mind our asking, how did you find out about this opportunity, and what initially attracted you to our company?  

3. Most of us have been here for at least five years, so we sometimes lose sight of what's going on in the outside world. Can you share with us what criteria you're using in selecting your next position, company or even industry relative to what you're seeing out there in the job market these days? 

Getting to the Heart of the Matter

Once the polite openers and inviting introductions have launched a healthy two-way conversation, it is time to get to the heart of the matter: the individual's philosophy of leadership and prior experience leading teams in similar situations.

"You can't be shy here. While these questions shouldn't border on challenges or demonstrate any kind of 'this is how we do things around here' perception, it's important to really open up on your end in a spirit of full transparency so that the candidate can feel comfortable doing the same," recommended Pete Tzavalas, senior vice president at Challenger, Gray & Christmas Inc., in Los Angeles. Typical questions that might follow the introduction include:

4. We prepared for this interview as a group in advance of today's meeting and determined that what keeps us happy and sticking around is our strong sense of independence and autonomy. Have you worked with groups that have longer tenure and a fairly deep level of expertise in their field, and if so, how would you manage that type of team?  

5. In terms of your communication style, do you tend to hold weekly staff meetings, quarterly one-on-ones and the like, or do you tend not to schedule your meetings in such a structured way?  

6. What's your philosophy on performance reviews? Do you love them or hate them, or are you somewhere in between? How would you advise us to make the most out of professional and career development opportunities while working for you?  

7. Do you prefer for your team to set goals and, if so, do you measure and evaluate them on a monthly, quarterly or annual basis? Likewise, how do you measure and track success?

8. What would you add or subtract to your current team (or a prior team) in order to strengthen performance or productivity?  

9. What's your general approach to addressing problematic performance issues? What can we expect in terms of your style when dealing with interpersonal conflict, and what's your philosophy surrounding "mistakes"?

10. Would you consider yourself more of a laissez-faire leader, or do you prefer providing ongoing structure, feedback and direction? How hands-on is your leadership style?

11. How would you prefer that we keep you in the loop and feed information to you? Do you like informal visits in your office or being copied on e-mails, or would you be interested in joining us in our client meetings?   

"Don't forget to invite the candidate to ask you open-ended questions about your individual or team dynamic, overall performance level, or the culture of the division or department you're working in," Tzavalas recommended. "It's important that this is a two-way street and transparent discussion for both sides equally." As such, your closing question might sound like this:

12. Sally, we've asked you a number of questions to get a feel for your leadership, communication and team-building style. What can we answer for you in terms of our culture, our way of doing things, how we get along with one another and the like?  

Interviewing your future boss may feel a bit awkward or unnatural, but you should appreciate when your company encourages it―the request is based on trust and respect for the work you do. The candidate gets to know the team, the team members have some say over who ultimately gets selected for the role and senior management benefits from the team's insight. It's a triple win based on trust, respect and transparency. 

Paul Falcone (www.PaulFalconeHR.com) is vice president of HR at the Motion Picture & Television Fund in Woodland Hills, Calif. Some of his best-selling books include 101 Sample Write-Ups for Documenting Employee Performance Problems, 96 Great Interview Questions to Ask Before You Hire, 101 Tough Conversations to Have with Employees, and 2600 Phrases for Effective Performance Reviews.