How to Hire Your Boss During a Job Search

— April 7, 2017

It’s as important as ever to remind yourself the interview process is a two-way street. Any company worth their salt is going to allow you as a candidate to ask questions of them and your potential new boss, to hire your boss just as they are moving to hire you.


To do this effectively, think about the interview process from a different angle. Pretend you are currently employed by the company and you are involved in the interview process to hire your next boss. What questions would be important to you? You know the type of people you work best with, so prepare questions that uncover if this boss will be able to help you succeed.


I’ve included a few topics as well as some sample questions below. These questions can be asked of the boss as well as potential peers. Asking both audiences highlight potential red flags and allow you to assess inconsistencies.


Twelve Key Questions to More Effectively Hire Your Boss


Management and Leadership Styles



  • How do you and your team make strategic business decisions?
  • During crunch time, who on your team is the last to leave?
  • What are the characteristics of the most productive people on your team?
  • What are the leadership qualities you look for when you hire for your team?

Marketing Capabilities



  • What has been the most successful campaign you and the team have managed recently?
  • How has that campaign been received by the company at large?
  • What’s the biggest challenge you have ahead of you for the marketing function at XYZ Company?
  • What external partnership with an agency or vendor is most critical to achieving your goals for the marketing team?

Make sure the questions you ask are appropriate for your situation. Be sure to customize the list above, focusing on areas important to you. And don’t forget real-time updates based on information you pick up during the interview process.


Your Own Reference Check


Along with the direct line of questioning, do your own reference checks as if you would hire your boss. Seek out people who have worked with or for the person in the past. Using LinkedIn can get you this information rather quickly. If you can’t find someone in your network, LinkedIn makes it easy to reach out to people outside of your network to ask for their opinion.


The other piece of research you should do is to use LinkedIn again to track the careers of others who are working there now and in the past. Here’s what to look for when researching these folks:



  • What’s their tenure in the roles they held?
  • Did they get promoted within the department?
  • Did they stay with the company but leave the department?
  • Did they take the time to leave a recommendation of their boss if they aren’t there anymore?

Collectively, this information should provide a much clearer picture about the boss you are hiring and if they are the right person for the job.

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