5 Questions to Ask Your Potential New Boss

by Danielle Foster

A new job isn’t just about getting hired — it’s about finding a match that’s right for both you and your prospective boss. Many candidates feel that they are not in a position to be picky about who they work with. But remember, as the adage goes, people leave managers not companies —and that’s especially relevant now, as companies compete for the best talent.

“I would rather take an imperfect job for an awesome boss — because an awesome boss is going to accelerate me — rather than the perfect job for a boss that’s not going to take any interest in me,” says Emily Bermes, an executive coach who runs her own consulting firm. “Go after the better boss every single time because it will completely change the trajectory of your career.”


To find a great match, here are five questions to ask in your interview.

  1. What is the onboarding process?
    According to Bermes, the fail rate, particularly at the executive level, is 40-50%. That is, nearly half of those hired don’t work out. They either get disillusioned and leave, or sooner or later they’re let go. Often, the failure results from an onboarding process that is handled so poorly that new hires don’t stand a chance. Ask your potential boss what a good onboarding looks like. This will help you understand the support you will get, what the learning curve will be — and whether it’s what you need to succeed in the position.


  1. Tell me a story that illustrates your management style.
    You could also phrase this question as “What type of team do you like to run?” If you do your best work autonomously and a potential boss tells you a story about how collaborative and integrative the team is, it’s a sign that your working styles may not gel.


  1. How do you give feedback?
    This can be an important question if you prefer to get regular feedback. We recommend asking if it’s part of the culture to give and receive feedback frequently, or if it’s something you would have to take the initiative to ask for.


  1. What are the typical hours?
    When you ask about hours you can also ask about how they communicate and which tools they use. This can tell you which medium they prefer — email versus Slack, for example — and how responsive they expect you to be, especially after hours.


  1. Can you please tell me a story that’s illustrates your corporate culture?
    Asking for a story will give you insight not only into what the company values but into other employees (successful and, perhaps, unsuccessful) as well. It’s important to ask about diversity and inclusion policies to get a sense of how you might be supported both by your boss and the organization as a whole.


Organizations do not want to make the wrong hire — it’s enormously expensive — and individuals don’t want to take the wrong role. Make sure that you, as the candidate, do your due diligence to find out if the job is a good fit for both yourself and your prospective employer.