Lesson 5.1
Running discovery interviews
You will be able to run an interview that gets facts about real past cases instead of opinions and polite agreement.
Why this matters on a client engagement
Your proof of concept is only as good as your understanding of the problem. People are kind in interviews: they say your idea sounds great and describe the process as it should be. An FDE who asks about the last real case, and listens more than talks, finds the exceptions, workarounds and numbers that decide whether a solution will work.
Shape of a discovery interview
- Open and set expectationsNo wrong answers; learning their work
- ContextRole, systems, who sends and receives work
- Last real caseStep by step, on screen if possible
- Dig into painSlowest step, what went wrong, how often
- Workarounds and numbersSpreadsheets, tricks, volumes, times
- Close with asksDocuments, shadowing, next person
The short version
A discovery interview is a structured conversation to learn how someone does their work, what goes wrong, and what it costs them. The most useful single technique is to ask about the last real case: 'Walk me through the last invoice exception you handled.' A specific, recent case has real details, real systems and real time spent. A general question such as 'How do you handle exceptions?' gets the official version.
Rob Fitzpatrick's book The Mom Test gives three rules that fit discovery well. Talk about their life, not your idea. Ask about specifics in the past, not generics or opinions about the future. Talk less and listen more. The name comes from the idea that even your mother would lie to you about your idea to be kind, but she cannot mislead you about facts from her own week.
Why opinions and future questions mislead
Questions like 'Would you use a tool that does X?' or 'How much time would this save you?' ask people to predict their own behaviour. Most people answer yes to be helpful, and their estimates are guesses. Compliments ('That sounds really useful') feel like progress but carry no information.
Facts from the past are different. 'How many exceptions did you handle yesterday? Which one took longest? What did you do?' gives you things you can check against system data later. When someone says 'always' or 'usually', ask for the last time it happened.
A simple interview structure
Forty minutes is enough for most interviews. Book an hour so you never rush the close, which is where you get access to the next source of evidence.
- Open (2 minutes): who you are, why you are here, that there are no wrong answers, and that you want to learn their work, not test them.
- Context (5 minutes): their role, their day, the systems they use, who they get work from and hand it to.
- Last real case (15 minutes): walk through one recent case step by step. Ask them to show you on screen if possible.
- Dig into pain (10 minutes): which step was slowest, what went wrong, what they did about it, how often that happens.
- Workarounds and numbers (5 minutes): spreadsheets, notes, personal tricks; volumes and times they can point to.
- Close (3 minutes): ask for documents, a chance to shadow, and who else you should talk to.
Question bank
The question 'Have you tried to fix this before?' is especially telling. If someone has built a spreadsheet or asked IT for help, the pain is real. If they have never done anything about it, it may be a minor annoyance.
- Tell me about the last time you did this. When was it?
- What happened just before it reached you? What happened after you were done?
- Which system did you have open? Can you show me?
- What took the longest? What were you waiting for?
- What did you do when it did not fit the normal steps?
- How did you know you had done it right?
- Have you tried to fix this before? What happened?
- If this problem disappeared tomorrow, what would you do with the time?
- Who else deals with this, and who decides how it is done?
Avoiding leading questions and taking good notes
A leading question hints at the answer you want. 'Isn't it frustrating to chase buyers by email?' leads. 'What happens after you email the buyer?' does not. Avoid naming your solution until the end, if at all. When you hear something interesting, ask 'Tell me more about that' or 'Why?' and then stay quiet. Silence feels awkward, but people fill it with the most useful details.
Take notes in three kinds: facts (what happened, with numbers), quotes (their exact words, in quote marks), and your own interpretations, clearly marked as yours. Write up within an hour while memory is fresh. If you record, ask permission first, and follow the client's policy on recordings and transcripts. Interview in pairs when you can: one person asks, the other writes.
Interview: AP clerk, 12 min call, 2025-03-04
Case: INV-102, price mismatch, raised 3 Mar
FACT Opened ERP exception queue, 41 items waiting
FACT Checked PO price vs invoice: 4 percent higher
FACT Searched shared mailbox for buyer approval, none found
QUOTE "I email the buyer and then just wait"
FACT Emailed buyer twice (4 Mar, 6 Mar); reply 7 Mar
FACT Tracks open items in a personal spreadsheet
MINE Waiting on buyer may be most of elapsed time
NEXT Ask buyer how approvals are decided; get ERP logWorked example
Worked example: rewriting a weak interview
A first-time interviewer asked an AP clerk: 'Would an AI that explains exceptions help you?' The clerk said 'Yes, definitely.' That answer is worthless: it is a prediction and a kindness.
Rewritten using the last real case, the same interview learned that the clerk handled 41 queued exceptions that week, that the longest one waited three days for a buyer reply, and that the clerk kept a personal spreadsheet to track chasers. Those facts point to a different problem than expected: the delay is waiting for approvals, not understanding the exception.
- Weak: 'Is the process slow?' Better: 'How long did the last one take from arrival to payment?'
- Weak: 'Would you use this?' Better: 'What did you use last time to work out the cause?'
- Weak: 'Do you find the ERP hard?' Better: 'Show me the screens you used for that case.'
Start practicing
Interview someone about their last expense claim
40 minGoal: Practise the last-real-case technique and fact, quote, interpretation notes.
- Find a friend or colleague who has filed an expense claim, booked travel or submitted a timesheet recently.
- Ask them to walk you through the last time they did it, using the structure and question bank from this lesson. Do not suggest any solution.
- Take notes in FACT, QUOTE and MINE lines as in the example.
- Within an hour, write up the case as a numbered list of steps with the time each took.
- Paste your questions (not their personal details) into Claude and ask it to flag any that were leading or about the future, then rewrite those.
Done when: You have a step list with times, at least three exact quotes, and a rewritten version of every leading question.
Fix ten bad questions
15 minGoal: Train your ear for leading and hypothetical questions.
- Write ten questions you might naturally ask about a process you want to improve.
- Mark each as past-specific, general, future or leading.
- Rewrite every one that is not past-specific so that it asks about a real recent case.
Done when: All ten questions ask about something that already happened and none hints at an answer.
Common mistakes
- Pitching your solution during the interview. Once people know what you want, they tell you what you want to hear.
- Accepting 'always', 'never' or 'usually' without asking for the last real case.
- Interviewing only managers. They know the official process; the people doing the work know the real one.
- Mixing your interpretations into the facts in your notes, so you later cannot tell what was said.
- Ending without asking for documents, shadowing time and the next person to talk to.
Check yourself
- What are the three rules of The Mom Test, in your own words?
- Why is 'Would you use this?' a poor discovery question?
- Rewrite 'Isn't the approval step a pain?' so it is not leading.
- What three kinds of notes should you keep apart, and why?