Five design thinking questions you can ask to boost insight

As an occasional interviewer I am often a bit stumped when coming up with questions at short notice.  This is my go-to grab bag of questions to get the most out of a design thinking interview.

1. Why?
Five year olds* are annoying for their repeated ability to keep asking "Why?" Why do they do it? Because it's staggeringly effective at getting to the heart of something. As an interviewer though, try to find ways to keep building empathy though focussing e.g. Why was that important to you at that time?

*Scratch that I know of one very smart sixteen year old who still does it.

2. What is your most memorable experience of xxxx?
This is a good question for tapping into strong emotion - positive or negative. It can open the floodgates sometimes.  Consider probing to find get more detail.

3. What is the most surprising thing about xxxx?
I've found it near impossible for an interviewee to give a blandly normal answer to this.

I recently asked a homeopath I know what the most surprising thing about their recent trip to India - and their answer involved doing a consultation for their taxi driver on the way to another appointment, why people go to homeopaths there and the near celebrity status some homeopaths have in India.

4. How would you rate your current experience of xxxx out of five, with one being the lowest and five being the highest?

To follow up, ask them why they gave it that rating. And then for additional insight ask them what a five, six, seven, eight, nine, ten, eleven or twelve star experience would look like.  You will likely get some crazy answers once you start asking them what it would take to get a twelve out of five rating - but it can also be very revealing and give you some fascinating directions to pursue in prototyping.

5. What is the question I should have asked but was too dumb to think it up?
This is a fantastic question to perhaps finish with as it demonstrates humility/self-deprecation and gives the interviewee the chance to air any final thoughts. If you've had any experience being interviewed then the chances are, you've sometimes walked away frustrated that the question you really wanted to be asked, wasn't.

Bonus tip:
Some of these questions will challenge your interviewee to think so don't be afraid to give them a few moments to mull on them.  Or if you have a chance, send them through in advance.  If your interviewee is really stuck, consider parking and coming back to them later on.