For more advice from the Staffing Advisors recruiting team, read our 2024 post, Elevate Your Interview Game: How to Ask Better Questions.

Have you ever taken a job and later regretted it?  Almost everyone has.  And many times you, the job seeker, could have avoided the disaster if you had only asked better questions during the interview.  Most job seekers do not ask nearly enough questions during the interview sequence.  And that’s a crying shame, because one of the best ways to impress a hiring manager is to ask smart questions.

I’ve worked in the executive search business over twenty years and I’m here to tell you, most hiring managers are not so great at hiring the best candidate.  So why would you leave your career in the hands of the hiring manager – someone who barely knows you, and who is not particularly good at making hiring decisions?

Right, you should not.   It’s completely irrational.

There is only one solution – you need to do a better job interviewing the hiring manager.

Some people feel this approach might be a breach of interview etiquette or be in bad form.  Nothing could be further from the truth.  Asking smarter questions puts you and the hiring manager into collaboration on solving your very first business problem together … and trust me on this, you really want to understand how well you collaborate BEFORE you take the job.

Here are some basic interview questions you should ask, but you need to go far beyond these.  Don’t rely on generic questions from us or from anyone.  Instead, do your homework.  Learn about the company, learn about the job, learn about what is expected of you in the job.  Ask the kinds of questions you would ask if you were already working there.

  • “How fast do you expect me to come up to speed on this job and what kind of training did you have in mind?”
  • “What kind of results do you expect of me, and by when?”
  • “Who will I primarily be working with to get the results you anticipate?  How are they to work with?”
  • “How many competing priorities will I have at any one time?”
  • “What are the biggest obstacles I will face on my way toward achieving the goals you set out?”
  • “How have other people fared in meeting your expectations?”
  • “How have other people failed in this job and how can I avoid that?”

Keep asking questions until you are absolutely sure that you understand what they expect from you, that you have the training and resources to be successful, and that you and your new boss can really work well together.