The Best Interview Question Ever

This is the question I ask everyone I interview. When people come to me for career advice or mentoring, I ask them this question as well. Just by asking this question and the ensuing conversation,  you can learn a lot about:

  • How important are professional titles to this person?
  • The importance of money / financial reward
  • Their ethics
  • Their cultural fit with your organization
  • Their ambitions
  • Their self-esteem
  • How well they work with others
  • Can they communicate a vision?
  • Are they introspective?
  • Are they a short-term or long-term thinker?
  • How likely are they to stay with your company?

This question is not “where do you see yourself in five years?” Instead, the question has a very important nuanced difference. The question goes like this:

“Most of us would like to retire someday, or at least not work as hard. When you think about retiring, what do you hope to retire from? That is, if you assume that you are retiring at the pinnacle of your career and have achieved all your professional goals, then what have you accomplished?”

For many people, that retirement is something far off in the future and they are taking each day as it comes. If you are hiring for a strategic, visionary role, do you really want to hire someone who hasn’t thought about their own career path, let alone your business? For others, they have some vague idea of a title or degree of compensation. That could be a sign that they are simply driven by money and will be gone when the next good offer elsewhere comes along. One memorable individual told me at length about her desire to help with humanitarian causes. The discussion helped both of us to realize that she was in the wrong industry, but today she has happily pursued those personally enriching goals. Another individual spoke of never wanting to retire. As we dug into this, it was clear that work defined this persons’s self-worth and they had few interests apart from it.

The magic to this question is that rather than force a stilted conversation about immediate goals, it puts both interviewer and candidate into a hypothetical yet realistic situation where there can be an honest dialog about things that have value to the candidate. Rather than a shallow discussion about whether the person will be a good fit for the company softball team, it enables the interviewer to get a legitimate read on the candidates ethics, communication style, and thus “cultural fit.”