100 Questions to Ask During a User Interview

No.	Item	Definition
1.	Can you clarify what you mean?	Requests clearer meaning.
2.	Can you compare those?	Invites direct comparison.
3.	Can you describe that moment?	Focuses on a specific moment.
4.	Can you estimate how often?	Requests a rough frequency.
5.	Can you give an example?	Requests a concrete example.
6.	Can you rank these options?	Asks for preference order.
7.	Can you remember a time?	Prompts a past example.
8.	Can you show me how?	Requests a live demonstration.
9.	Can you think aloud?	Invites spoken reasoning.
10.	Can you walk me through it?	Invites a step-by-step explanation.
11.	Did anything go wrong?	Asks about failures.
12.	Did anything surprise you?	Looks for unexpected reactions.
13.	Did this meet your needs?	Checks need fulfillment.
14.	Did you change your mind?	Explores decision changes.
15.	Did you feel in control?	Assesses sense of control.
16.	Did you hesitate anywhere?	Looks for hesitation points.
17.	Did you look for alternatives?	Checks alternative seeking.
18.	Did you need help?	Checks for support needs.
19.	Did you skip any steps?	Finds omitted actions.
20.	Did you trust the result?	Assesses trust in outcomes.
21.	How confident do you feel?	Measures confidence level.
22.	How did you learn this?	Asks about learning sources.
23.	How difficult is this now?	Assesses current difficulty.
24.	How do new people learn it?	Explores onboarding and training.
25.	How do you check your work?	Asks about verification habits.
26.	How do you choose a tool?	Asks about selection criteria.
27.	How do you decide?	Explores decision-making.
28.	How do you do this today?	Explores the current process.
29.	How do you feel afterward?	Explores post-task feelings.
30.	How do you feel during this?	Explores emotions in context.
31.	How do you keep track?	Asks about tracking methods.
32.	How do you know it’s done?	Defines completion criteria.
33.	How do you measure success?	Asks about success metrics.
34.	How do you prepare for this?	Asks about preparation steps.
35.	How do you prioritize tasks?	Explores prioritization approach.
36.	How do you recover from errors?	Explores error recovery.
37.	How do you share this?	Explores sharing behavior.
38.	How long does this take?	Measures task duration.
39.	How much effort is involved?	Measures required effort.
40.	How often does this come up?	Measures frequency of the task.
41.	How urgent is this?	Measures urgency.
42.	Is there a better way?	Invites improvement ideas.
43.	Is there a workaround?	Asks about unofficial solutions.
44.	Is there anything missing?	Looks for gaps.
45.	Is there anything unnecessary?	Looks for excess elements.
46.	Is this a high priority?	Assesses priority level.
47.	Is this what you expected?	Checks expectation match.
48.	What actually happened?	Compares reality with expectations.
49.	What almost stopped you?	Finds near-blockers.
50.	What are you trying to do?	Asks about the user’s goal.
51.	What do you call this?	Asks for the user’s term.
52.	What do you do after that?	Explores later steps.
53.	What do you do manually?	Identifies manual work.
54.	What do you expect to happen?	Asks about expectations.
55.	What do you worry about?	Surfaces concerns and risks.
56.	What does this mean to you?	Explores personal interpretation.
57.	What feels confusing here?	Identifies confusion points.
58.	What happened last time?	Asks about a recent example.
59.	What happens next?	Continues the process flow.
60.	What information do you need?	Finds needed inputs.
61.	What information is missing?	Finds missing inputs.
62.	What is frustrating about it?	Surfaces pain points.
63.	What is the first step?	Identifies the starting point.
64.	What made that difficult?	Explores cause of difficulty.
65.	What made that easy?	Explores cause of ease.
66.	What made you choose that?	Asks about selection reasons.
67.	What made you confident?	Finds confidence drivers.
68.	What made you hesitate?	Finds hesitation causes.
69.	What made you uncertain?	Finds uncertainty drivers.
70.	What matters most to you?	Reveals top priorities.
71.	What options do you compare?	Asks about alternatives considered.
72.	What problem are you solving?	Asks about the core need.
73.	What seems unclear here?	Finds unclear parts.
74.	What slows you down?	Finds blockers and delays.
75.	What stands out to you?	Finds notable elements.
76.	What takes the most time?	Finds time-consuming parts.
77.	What tools do you use?	Asks about current tools.
78.	What triggered this need?	Explores what started the need.
79.	What were you looking for?	Asks about sought information.
80.	What works well right now?	Finds current strengths.
81.	What would make this easier?	Asks for improvement ideas.
82.	What would make you quit?	Finds abandonment triggers.
83.	What would make you trust it?	Explores trust factors.
84.	What would make you try it?	Finds adoption motivators.
85.	What would stop you?	Finds barriers to action.
86.	What would success look like?	Defines a successful outcome.
87.	What would you change first?	Asks for top improvement.
88.	What would you do instead?	Explores alternative actions.
89.	What would you expect next?	Asks about next-step expectations.
90.	What would you keep the same?	Finds valued elements.
91.	When do you usually do this?	Asks about timing and context.
92.	Where does this happen?	Asks about the setting.
93.	Who is involved in this?	Identifies other people involved.
94.	Why is this important to you?	Asks about personal importance.
95.	Would you need training?	Checks training requirements.
96.	Would you pay for this?	Tests willingness to pay.
97.	Would you recommend this?	Tests likelihood of recommending.
98.	Would you switch from current?	Tests switching willingness.
99.	Would you trust this data?	Assesses trust in information.
100.	Would you use this again?	Tests repeat-use intent.