Qualitative interview questions are open questions that ask a person to describe their own experience in their own words, so you learn how something happens and why, not how often. Example: “Walk me through the last time you filed an expense report.” A structured interview asks everyone the same questions in the same order; a semi-structured interview keeps a short list of topics and lets the probes follow what each person says. Below: 55 questions sorted by what they ask for and by the interview you’re running, each with the probe for a vague answer, and a four-part structure for the guide.
The described process and the real one differ. Requests get in through people, and the data is used to justify them after the fact.
The first answer in an interview is usually the tidy version. A probe built from the person’s own words gets the messy, useful one. Four examples, none of them real people.
The described process and the real one differ. Requests get in through people, and the data is used to justify them after the fact.
Success is one workflow, in one group, by one date. Not a general adoption chart.
The gap isn’t documentation, it’s knowing which document is current. One person is quietly carrying it.
“Fit” was an export format. The cancellation followed a repeated manual fix, which is something that can be changed.
In practice most qualitative interviews end up semi-structured: a fixed list of topics, a flexible order, and probes that follow the person. The questions on this page work in any format; the format decides how much you stray from the list.
| Structured | Semi-structured | Unstructured | |
|---|---|---|---|
| What you bring | The same questions, in the same order, for everyone | Three to five topics, each with a main question and probes | One opening question and the topic in your head |
| What you get | Answers you can compare across people | Depth on the topics you chose, plus what you didn’t expect | Whatever mattered most to the person |
| Use it when | Many interviewers, or you need to count answers | You know the topics but not the answers | Very early, when you don’t yet know the topics |
| Risk | You miss what you didn’t ask about | Interviews drift if the probes aren’t written down | Hard to compare; easy to run out of time |
Grand-tour questions ask for a walk through a normal day or a normal task. They’re easy to answer, and they hand you the person’s own words to probe with for the rest of the hour.
Walk me through a normal week in your role.
Pick last week. What took the most of your time?
How did you come to be doing this work?
What was the first job or project where this became part of your day?
Walk me through what you did the last time you [did the task].
Where in that did you pause, go back or ask someone?
What are you trying to get done when you use [the product or process]?
What does done look like: what do you hand off, send or close?
What does a good day in this work look like?
Think of the last good day. What happened that made it one?
Ask about the last time, not the usual time. “Usually” is a story; “last Tuesday” is evidence.
Describe the last time you [did the task], step by step.
Which step, if any, do you do differently from how you were shown?
What did you do right after you noticed the problem?
Who, if anyone, did you tell first?
How do you keep track of [the thing] today?
Describe what that looks like right now, as it is, not as it should be.
What do you do when [the tool or process] doesn’t work the way you expect?
What did you do the most recent time that happened?
Which parts of this do you do by hand?
How long did the by-hand part take the last time you did it?
What have you stopped doing that you used to do?
What made it not worth doing anymore?
These ask what the person thinks should happen. Probe them with what did happen, so an opinion comes with a story behind it.
What do you think is the most important part of this work?
What happens when that part goes badly?
How well does the current way of doing this work for you?
What’s one thing about it you’d keep exactly as it is?
What would you change first if it were up to you?
What has stopped that change from happening so far?
How do you decide when something is good enough to send?
Think of the last time you were unsure. What tipped it?
What do people outside this work get wrong about it?
What would they see if they sat with you for a day?
Ask these after the facts are on the table, not before. A feeling question too early gets “fine”; asked about a specific moment, it gets the real reaction.
Take me back to the moment [the event] happened. What went through your head?
What part of it stayed with you the longest?
What part of this work do you look forward to?
What did it feel like the last time that part went well?
What part of this wears on you?
When in the week does that hit hardest?
How sure of yourself do you feel when you [do the task]?
Think of the last time you did it. At which point were you least sure?
How do you feel about the way this is changing?
What would the change have to get right for you?
Five checks before a question goes in the guide. The first two catch most of the problems.
Start with what, how, walk me through, or tell me about. A yes/no question ends the turn.
“Usually” invites a summary. The last time invites a story with details you can check.
Two questions in one sentence get one answer, and you won’t know which.
A question that names the problem gets agreement, not information. See biased and leading questions.
Jargon from your side of the table makes people guess what you mean. Say the thing the way they’d say it, then echo their word in the probe.
What the person knows, and how they came to know it. The second half is where the gaps in training, documentation and handoffs show up.
How does [the process] work here, as you understand it?
Which part of that did you have to work out yourself?
What rules do you follow when you [do the task]?
When did one of those rules last get in your way?
Who do you go to when you’re stuck on this?
What did you ask them the last time?
What would a new person need to know on day one?
What took you the longest to learn?
What do you know now that you wish you’d known when you started?
How did you find that out?
When a person can’t name what’s wrong, the difference between two cases usually names it for them.
What’s different about doing this now compared with a year ago?
Which of those differences was your choice?
What separates a handoff that goes well from one that doesn’t?
Think of the last bad one. What was missing?
How does the way you were trained to do this compare with how you actually do it?
When did the two first come apart, if they have?
If you had half the time for this, what would you drop?
What would break, if anything, once it was dropped?
What do you do differently from the colleagues who do the same work?
What happened that made you switch to your way?
The last five minutes often hold the best answer, because the person has warmed up and you’ve stopped steering. Leave room for it.
What haven’t I asked about that matters here?
Tell me about the last time that came up.
Of everything we talked about, what matters most to you?
What would change for you if that one thing were sorted?
Who else should I talk to about this?
What do they see that you don’t?
What would you like me to take away from this conversation?
If you had one sentence to put in my notes, what would it say?
A guide is one page: the opening, three to five topics, the probes you keep beside you, and the closing. Write it so a colleague could run the interview from it.
Ask about what they did, what it cost them and what they’d do without you. Questions about whether they like your idea get polite answers; there’s a fuller set for founders in questions to ask customers.
What were you trying to do the first time you looked for something like this?
What had you tried before that?
Walk me through the last time you used it, from opening it to closing it.
At which point did you switch to another tab or tool?
What surprised you, good or bad, when you started using it?
When did that surprise wear off, if it has?
What would tomorrow look like without it?
How long before that stops being a problem, if it does?
What does it cost you when it doesn’t work?
Who notices first when that happens?
How do you explain what it does to a colleague?
What did the last person you told ask you back?
Run these at kickoff, one person at a time. You’re after four things: what success looks like, what’s been tried, what could stop the project, and how each person wants to be involved.
What does success look like for this project a year from now?
What’s the first number or event that would tell you it’s working?
What has already been tried here?
What happened to that attempt?
What would make you call this project a failure?
What early sign would you watch for?
Who else has a stake in how this turns out?
What do they need from it that’s different from what you need?
What decisions are you waiting on this project to make?
What happens to that decision if the project slips a quarter?
How do you want to hear about progress?
What did the last useful project update you received look like?
What constraints should we know about before we start?
Which of those could move, if the case for it were strong enough?
What do you hear from users or customers about this today?
What was the last thing one of them said to you about it, as close to their words as you can?
For stay interviews, onboarding check-ins and research into how work gets done. These are easier to answer honestly one at a time than in a group; employee feedback questions has the survey version.
What part of your work would you protect if things got busier?
What was the last thing that threatened it?
How do you find out about decisions that affect your work?
Think of the last one. How long after it was made did you hear?
What slows you down that shouldn’t?
Roughly how much of last week went to it?
What did your manager do last month that made your week easier?
What would you have done without it?
What would have to change here for you to start looking?
Think of the last time you felt that. What set it off?
What do you want to be doing in two years?
What would that look like on an ordinary Tuesday?
A handful of interviews a week is what one person can run well, and the notes pile up. When you need the same conversation with forty people, Spoke asks your questions in the browser and follows up on each answer. The limits are stated on AI-moderated interviews.
Open questions that ask a person to describe their own experience in their own words, such as “Walk me through the last time you filed an expense report.” They aim at how something happens and why, rather than how many people do it.
“Walk me through what you did the last time you…”, “What did you do right after you noticed the problem?”, “What separates a handoff that goes well from one that doesn’t?” and “What haven’t I asked about that matters here?” Each is open, asks about one thing, and points at a real moment.
For a 45 to 60 minute interview, plan three to five topics with one main question each and two probes written down for each. That’s about 8 to 15 written questions, with time left to follow what the person says.
Structured: the same questions in the same order for everyone, so answers compare. Semi-structured: fixed topics, flexible order, probes that follow the person. Unstructured: one opening question and a conversation. Most in practice are semi-structured.
Short follow-ups that ask the person to go deeper into what they just said: “When was the last time?”, “What happened next?”, “What did that cost you?” They turn a general answer into a specific one. The full set is in the probing questions guide.
Four things: what success looks like and the first sign of it, what has already been tried, what would make them call the project a failure, and how they want to be involved and informed. Ask one person at a time, at kickoff.
Enough that the last few interviews stop surprising you. For one question in one group, five to ten is a common starting point; add more when each group you care about is smaller than that.
Thirty to sixty minutes is the common range. Shorter loses the closing questions; longer loses the person.
Spoke asks the follow-ups for you, with every person. Free to start, no card. Your first ten agent surveys are on us.
