Unlock Interesting Answers With This One Great Question

First-time conversations often follow a pretty standard form that yields only the barest level of insight. All of us are used to our own answers and can give them on auto-pilot; therefore, everyone is on some degree of auto-pilot and conversations can be rote.

Some time ago I hit upon a question that, when posed to someone who was telling me about their job or some previous life experience, can break the auto-pilot problem and lead to real insight.

The question essentially is, “what surprised you about (insert job/experience they had)?”.

There are many forms I use of this question – for instance, I might say about someone’s current role “what would surprise someone who learned more about your job?”, or “what did you learn from that?”.

I have found that since these are not typical questions, it breaks the auto-pilot mode and many times people will actually think about their answer. I have heard some really interesting insights from people responding to this question, and oftentimes they seem as if they hadn’t really thought of the question until now (the question itself can be a surprise). As a result, the answer seems fresher and more honest.

Other advantages of this question….

• It forces the respondent to think from the perspective of someone who is unfamiliar with the job or experience they are talking about, therefore they avoid uninteresting detail or jargon.

 

• It conveys respect to the respondent. Every job or experience has complexities that are hidden from plain view, and people often feel like what they have to do to deliver results can be invisible to others. This question gives them an opportunity to tell you about those complexities in a way that is understandable.

 

• The word “surprise” is key – I find it causes the respondent to dig one level deeper than “learn” (e.g. “what surprised you” causes more thought than “what did you learn”). Although either question is great to ask, consider using “surprise” in your question.

Bonus: this is a great question to ask in an interview because it gets the interviewee out of their own interview auto-pilot mode and you get a better insight into who they are and what they’ve accomplished.

This is a fun question to ask that will lead to great conversations. Take it out for a test drive and enjoy the results.

Good luck!