Interviewing for a Job? Don’t Forget to Interview your Boss

April 18, 2019

Why is it that companies tend to call the shots in the interview process?

When a company makes a new hire, the hiring manager is empowered to do what it takes to get to know the candidate, how they’ll fit with the team and what skills they’ll bring to the table. That just makes sense, right?

After all, the manager will invest a lot of time in that new team member, and a poor fit could set the entire team back, hurting the manager's performance and ultimately the company’s success.

The thing about fit is, it’s never one-sided. Candidates should really know what they’re getting into before they sign a contract, but they rarely do.

The job you choose is an investment in your future self. It’s about so much more than the paycheck or the title on your LinkedIn. This one decision could impact your life for years to come.

So how do you tell if a job will give you a good return on your investment? Your boss could be the single most important factor.

Your relationship with your boss, in no small way, will shape your professional development, your experience at work, and in turn, the trajectory of your career.

The problem is, it’s not up to you to choose your own boss, right? I believe that assumption is a relic of the old “employer-first” world. Top-down hiring doesn’t actually work!

To get the most out of every hire, it’s in a company’s best interest to find the right match between employees and managers. Bottom line, as a job seeker, you can and should make the effort to get to know your boss, just like they get to know you.

I’d like to share a few data points from research to illustrate the importance of picking the right boss:

  • A boss’ technical competence is the single strongest predictor of a worker’s job satisfaction according to a 2015 study.
  • A Gallop study of 7,200 US employees found that more than 50% of people had quit a job because of their boss.
  • Another Gallup study found that at least 70% of the variance in employee engagement is attributed to the quality of their managers.

If you want to dig deeper into the science behind my advice, I’ve listed several additional research articles that you can reference at the end of this article.

Despite ample evidence that an employee’s fit with their manager will impact their happiness, engagement and longevity at their job, I’ve yet to see an example of a company that puts the manager’s name on a job description.

Traditional hiring practices aren’t set up for you to make informed decisions about which boss to work for, so you have to learn how to do your research and bend the rules, without breaking your chances of getting hired.

Most people have been trained to search for the right job, not the right boss, so the idea of looking for a boss might feel a bit awkward, inappropriate even. It’s not exactly common practice for employees to get to interview their future manager, but for in-demand talent, it doesn’t have to be that way.

I’m not saying you should walk into an interview and demand a lineup of potential managers to choose from; it takes a bit more finesse than that. But if you show an employer that you’re being inquisitive for all the right reasons, doors can open up for you to get what you want.

And if you’re searching for a new job, you should want more than anything to interview your boss.

How to Choose a Boss

Let’s start with the premise that what helps you perform your best as an employee will be just as good for your employer as it is for you. It’s up to you to communicate that!

To be successful, I suggest you follow two simple rules for navigating the interview process. First, be respectful, and second, make sure to actually interview your boss before you accept an offer.

Respect the Interview Process

If the standard process is not set up for you to get to know your future boss (which at most companies, it’s not), you’re going to have to shake things up, respectfully.

At some point, you should ask to meet your future boss, but you don’t have to do this from day one of the interview process. In fact, please don’t. Every person you meet during the interview is giving up some of their time to meet you—and for management that time is particularly valuable—so be respectful and be patient.

Early in the interview process, what you should do is set expectations and explain your thought process to the recruiter. Here’s an example of a script you might use:

I believe the boss I report to will be instrumental in my success at this company, and I want to make sure that I understand their expectations for this role. Will there be an opportunity for me to meet my supervisor at some point in the interview process? Could you share their LinkedIn URL so that I can get to know a bit about them?

Even though you may not meet them right away, try to find out who your future boss would be as early as possible. That will allow you to research them online and start digging for nuggets of insight throughout the interview process.

Ask various coworkers to explain how they view the boss’ working style, competence and expertise. Meet your future team prior to making a decision too, and ask them to explain what it’s actually like to work under their boss. Sometimes second-hand information about a person can be even more telling than their own self-evaluation.

Once the company has expressed serious interest in hiring you, you can and should ask to interview your actual boss in person.

Even if they’ve already interviewed you, ask for another meeting to learn more about them and their expectations of you. That might not be part of the typical interview process, but if you’ve demonstrated your intentions well from the beginning, and put in the effort to explain why it matters, your employer should see this as a sign of maturity and conscientiousness, not disrespect.

What to Ask Your Boss in An Interview

By the time you find yourself face to face with your boss, you should already have enough knowledge about them to take your conversation beyond surface-level topics.

You don’t want to waste any questions on things that you could have figured out with a quick Google search, so come prepared with plenty of research. Do you have any overlap in your academic or professional background? Has your boss been quoted in any press articles? What major accomplishments might have gotten them to this level?

Use your time with your boss to understand how you will relate to them and what you could learn from them. I recommend evaluating this based on four criteria:

#1 Overall Caliber

Ask yourself whether you would really look up to your boss and want to be taken under their wing, or be frustrated, thinking ‘this is my boss?’ all the time. An impressive boss will set a high standard for you; an unimpressive one could kill your motivation. And don’t forget, an exceptional leader has a promising career ahead of them, which could open doors for you down the road.

Example question: What has been the most important milestone or accomplishment in your career?

#2 Overlap with Your Learning Goals

Look for overlap between the skills and knowledge you want to gain and the expertise your boss has. If you’re in a senior role and have some experience in these areas, try to get a sense of how much of an expert the boss really is compared to you.

Example question: I’m hoping to improve [XXX skill]. How much experience do you have with this, and are there any projects in this area that we could work together on?

#3 Personal Style

More likely than not, your manager is in their role because they’re good at what they do. That doesn’t necessarily mean that you’ll work well with them, or enjoy reporting to them. Try to assess how well their management abilities line up with their technical abilities, and how well you connect on a personal level.

Example questions: How would you describe your management style and your relationship with your team?

#4 Boss’ Perception of You:

The employee-boss relationship is a two-way street. Make sure your boss’ expectations for this role are aligned with yours.

Example questions: How do you expect this role will contribute to the team’s goals? What does success look like? How can I develop and grow in this role?

Evaluate Your Options and Choose the Right Boss

If you’re considering multiple opportunities, you’re probably weighing the pros and cons at each company. I recommend putting significant weight on your relationship with the boss.

Personally, I’d take an exceptional boss over a role that pays more any day.

That might sound irrational since you never know when the team will get restructured, but if you work hard to make a good impression, a connection with a great boss could continue to serve you for years beyond this role. Perhaps the boss will take you with them if they get promoted or move on to another opportunity. Perhaps they’ll become your long-term career mentor. At the very least, they’ll probably be the first person your next employer calls for a reference, and their good word could help you make your next move.

On the other hand a poorly matched boss could make it difficult for you to grow as a professional or show value at your company.

So what if your dream company has matched you up with a boss that really isn’t a fit? That’s a situation that will need to be handled delicately.

To avoid undermining or offending the boss, your best bet is to speak with them directly rather than making a “complaint” to the recruiter. If you can tactfully explain why your skills and learning goals are out of sync, you may be able to come to a mutual conclusion that the relationship is not the best fit. Once that’s established, if the company really wants you, and with your initially intended boss’ support, the company might be willing to consider pairing your with a different manager, or considering you for a different role in future.

It’s a risky move, and you may lose the opportunity to join the company, but signing on to work for someone you don’t get along with is at just as risky for your career—if not more.

Don’t forget, when it comes to matching up with a boss, what’s good for you is good for your employer. Don’t settle for a match that will set you up for failure.

Further Reading:

  • John F. Helliwell, Max B. Norton, Haifang Huang, Shun Wang (2018). Happiness at Different Ages: The Social Context Matters
  • Alfred Michael Dockery (2003). Happiness, Life Satisfaction and the Role of Work: Evidence from Two Australian Surveys.
  • Benjamin Artz, Amanda H Goodall & Andrew J Oswald (2015). Boss Competence and Worker Well-being.
  • Justin Conway (2011). Effects of Supervisor-Employee Relationship on Job Performance
  • Bauer, T.N., & Green, S.G. (1996). Development of leader-member exchange: A longitudinal test. Academy of Management Journal, 39, 1538-1567.
  • Elangovan, A.R., & Xie, J.L. (1999). Effects of perceived power of supervisor on subordinate stress and motivation: The moderating role of subordinate characteristics. Journal of Organizational Behavior, 20(3), 359-373.
  • Erdogan, B., & Liden, R.C. (2002). Social exchange in the workplace: A review of recent developments and future research directions in leader–member exchange theory. In L. L. Neider & C.A. Schriesheim (Eds.), Leadership (pp. 65–114). Greenwich, CT: Information Age.
  • Miles, E.W., Patrick, S.L. & King, W.C. 1996. Job level as a systemic variable in predicting the relationship between supervisory communication and job satisfaction. Journal of Occupational and Organizational Psychology 69: 277-292
  • Edward P. Lazear, Kathryn L. Shaw, Christopher T. Stanton (Stanford 2012). The Value of Bosses.