Interviewing Users: How to Uncover Compelling Insights

• Ask about relationships. “How do you work with new vendors?” This general question is especially appropriate when you don’t even know enough to ask a specific question (such as in comparison to the earlier example about streaming movies). Better to start general than to be presumptive with a too-specific question.
• Ask about organizational structure. “Who do the people in that department report to?”
Questions that probe what’s been unsaid:
• Ask for clarification. “When you refer to ‘that,’ you are talking about the newest server, right?”
• Ask about code words/native language. “Why do you call it the bat cave?”
• Ask about emotional cues. “Why do you laugh when you mention Best Buy?”
• Ask why. “I’ve tried to get my boss to adopt this format, but she just won’t do it....” “Why do you think she hasn’t?”
• Probe delicately. “You mentioned a difficult situation that changed your usage. Can you tell me what that situation was?”
• Probe without presuming. “Some people have very negative feelings about the current government, while others don’t. What is your take?” Rather than the direct “What do you

Ask about sequence. “Describe a typical workday. What do you do when you first sit down at your station? What do you do next?”
• Ask about quantity. “How many files would you delete when that happens?”
• Ask for specific examples. “What was the last movie you streamed?” Compare that question to “What movies do you stream?” The specific is easier to answer than the general and becomes a platform for follow-up questions.
• Ask about exceptions. “Can you tell me about a time when a customer had a problem with an order?”
• Ask for the complete list. “What are all the different apps you have installed on your smartphone?” This will require a series of follow-up questions—for example, “What else?” Very few people can generate an entire list of something without some prompting.

You can provide him with sticky notes to write his questions on as he thinks of them (so even if the asking is deferred, at least capturing the question provides some—albeit muted—immediate gratification).