Cultivate a mindset of “general non-specific curiosity”
Your job is to learn about how this person thinks about/does/interacts with [something] with lots of specifics
Tell the person this is your job: “Hi, I’m Christina, and I’m working on a new startup. I’m here to learn more about how you communicate with other teams at Airbnb.”
The more stories you can get someone to tell you — or show you — the better. Stories tend to be where all the interesting stuff lies.
Try to do interviews in their world — their office / home / etc., as it helps you better see/understand their worldview. (It’s also often logistically easier for these people, too.)
Avoid phone calls, which are tough, because it’s more difficult to infer meaning, understand vocal intonation, read body language, and ultimately, understand what really matters to the person.
Interviews aren't normal meetings. Embrace that! You can ask seemingly-silly questions under the cover of “being on an interview” without problem. Framing the interaction:
If you're not fully comfortable, the other person will be able to tell. (Humans are very good at telling when another human is uncomfortable.) That’s fine! If you’re uncomfortable, play up the fact that you’re not in a normal meeting and lean into a structured interview.
If you can take photos — of the person, their workspace, their screen(s), their tools, etc., try to. It can be nice for the rest of us at the office. (Ask permission before you start taking photos!)
Write what you’re hearing; don’t try to do analysis in the moment. (“Works for 8 hrs/day, 7 days/week” vs “WORKAHOLIC.”) Do this because:
Beside your questions, you say ..
Always ask open-ended questions
Ask the shortest question you can
Suggest that they think aloud. Filters are bad!
After you ask a question, be quiet (even if it's awkward) The other person will fill in the silence.
For most topics, you’ll need a series of questions to get to the information you want. After you’ve been given an answer, reflect whether it really gives you all you want to know; if it doesn’t, ask something further.
As people talk, you’ll think of lots of questions to ask. Your challenge / goal is to keep those threads in your mind but not let them derail the interviewee.
* *In general, these questions are designed to get someone talking about something specific.
Ask about a specific occurrence “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 from which you can ask more questions.
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 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.
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?”
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 think about our government?” or “Do you like what the government is doing lately?” This indirect approach offers options associated with the generic “some people” rather than the interviewer or the interviewee.
Explain to an outsider “Let’s say that I’ve just arrived here from another decade, how would you explain to me the difference between smartphones and tablets?”
Teach another “If you had to ask your daughter to operate your system, how would you explain it to her?”
Compare processes “What’s the difference between sending your response by fax, mail, or email?”
Compare to others “Do the other coaches also do it that way?”
Compare across time “How have your family photo activities changed in the past five years? How do you think they will be different five years from now?” The second question is not intended to capture an accurate prediction. Rather, the question serves to break free from what exists now and envision possibilities that may emerge down the road. Identify an appropriately large time horizon (A year? Five years? Ten years?) that helps people to think beyond incremental change.
A few ending questions you can use:
Remember the "doorknob phenomenon": people say the most interesting stuff when your hand is on the doorknob — so be ready to listen to (or receive) their “one more thing”