Needs more than a quick edit9 of 12 checks passed
The guide is strong and actionable, but it violates the 900-word constraint and lacks explicit must-ask/cut guidance for the 30-minute call. A PM would need to trim and tighten it before using it as-is.
Output
Autochase Discovery Calls: Interview Guide
Interviewers: Mei and Tomas | Calls: 8 × 30 min | Week of: [date]
Why we're doing this
Sam's hypothesis is that late payments cost our users real money, and chasing them is painful enough that they'd pay $10 a month to automate it. The data leaves room for doubt. 34% of invoices are paid late, but only 12% of accounts used "Send reminder" in the last 90 days. Either chasing isn't painful, or people chase outside Paydeck, or they avoid chasing altogether. These calls should tell us which.
Learning goals
- Cost: How much do late payments actually hurt (cash flow, hours, stress)? Is this a top-three problem or a mild annoyance?
- Current behaviour: How do people chase today, with what tools, and why do most not use our reminder button?
- Barriers to automation: Would they let software chase their clients? What would make that feel safe or risky?
- Willingness to pay: Do they already spend money or time on this, and who (freelancers or agencies, Pro or free) feels it most?
Who we talk to
Draw from accounts with at least one invoice paid 7+ days late in the last 90 days, then fill these slots:
| Segment | Calls | Why |
|---|---|---|
| Regular "Send reminder" users | 3 | They feel the pain and act on it |
| Late invoices, never used the button | 3 | The 88% we know least about |
| Filed a ticket asking for auto-reminders | 2 | Our strongest likely advocates, to test them |
- Aim for at least 5 Pro accounts, since the add-on is priced against a $12 plan.
- Include at least 2 agencies.
- Invite about 15 people to get 8 who show up.
- Hand-pick from the people who reply. Don't just book the first eight.
- Offer a thank-you, such as a free month of Pro.
Why this differs from Sam's plan: Emailing only the 300 heaviest button users would reach people who already chase inside Paydeck. They're the most likely to say yes, so a yes from them wouldn't tell us much. Booking the first eight repliers adds another bias toward the most engaged users.
The call (30 minutes)
0–3 min: Open - "Thanks for your time. We're trying to understand how you get paid. We're not selling anything, and there are no wrong answers." - Ask permission to record.
3–8 min: Context - "Tell me about your business. Who are your clients, and how many invoices do you send in a typical month?" - "Walk me through what happens after you send an invoice."
8–18 min: The last late invoice (the heart of the call) - "Think of the last time a client paid you late. What happened?" - "When did you notice? What did you do, and when?" - "How did it get resolved? How long did it take?" - "What did it cost you: time, money, other plans, stress?" - "Is that typical, or was it unusual?"
18–24 min: How they chase today - "What do you usually do when an invoice is overdue?" - "What tools do you use: email, phone, our reminder button, anything else?" - If they haven't used the button: "Have you seen our 'Send reminder' button? Why or why not?" - "Is there anyone you chose not to chase? Why?" - "What worries you about chasing clients?"
24–28 min: Value and alternatives - "Have you tried to fix this: templates, other software, an assistant, late fees?" - "What did that cost, and why did you keep or drop it?" - "If this problem disappeared tomorrow, what would change for you?"
28–30 min: Close - Describe Autochase in one or two neutral sentences: "automatic reminders for overdue invoices, sent on a schedule you set." - Ask for their reaction. - Then ask: "Would you want to join a paid beta when it's ready?" A yes should come with a real next step, such as their email for the beta list. - Finish with: "Anything I should have asked?"
Why this differs from Sam's questions: Questions like "Would this be useful?" or "How frustrating is it?" invite polite yeses. Offering $5/$10/$15 anchors people on our numbers. Asking what their clients would think gets guesses, not evidence. "Other features" takes the call off topic. Asking what actually happened last time gives us far more reliable answers.
Notes for first-time interviewers
- Split roles. One person leads and the other takes notes. Swap after each call.
- Ask about the past, not the future. "What did you do?" beats "What would you do?"
- Follow up before moving on. "Tell me more," "Why?" and "Can you give an example?" are your best questions.
- Get comfortable with silence. Count to five before filling a pause. People often add the useful part then.
- Don't pitch or defend. If they criticise Paydeck, say "That's helpful, go on."
- Treat compliments as noise. "Sounds great!" means nothing. Look for money spent, time lost and workarounds built.
- Write down exact quotes. Mark the ones about cost or emotion.
- Debrief for 10 minutes right after each call. Cover the top three surprises, the evidence for or against each learning goal, and whether they meet the go signals below.
Decision criteria
We're agreeing these before the calls so we don't rationalise afterward. Eight calls give us direction, not proof. Treat the results as a reason to prototype or to drop the idea, not as a sizing exercise.
Go ahead (build a prototype next quarter) if: - At least 5 of 8 describe a recent late payment with a concrete cost, such as a cash-flow squeeze, hours spent chasing, or a delayed bill of their own; and - At least 4 already use a workaround (templates, calendar nudges, another tool) or have paid for one; and - At least 3 give a real commitment at the close, such as joining the beta list or asking when it launches; and - Relationship worries come up but sound solvable, for example with control over tone, timing or which clients get reminders.
Stop or rethink if: - Most treat late payment as normal and tolerable ("they always pay eventually"); or - Most avoid chasing on purpose to protect client relationships, and automation makes them more nervous; or - The pain is real but they're satisfied with what they already use; or - Interest is limited to the ticket-filers and heavy button users.
Possible middle outcome: People want the feature but balk at paying extra. That points to making it part of Pro rather than a $10 add-on, which nearly doubles the price. Flag this if you hear it.
After the calls
Mei and Tomas share a one-page summary with Sam within two days. It should cover each learning goal, the go/stop tally, and the three best quotes.
Claims the judge couldn’t find in the brief
- Either chasing isn't painful, or people chase outside Paydeck, or they avoid chasing altogether.
- Heaviest reminder users are the most likely to say yes.
Grades and run details
Decision model 96 · LLM judge 9 of 13 checks
Decision model checks
- passUses the supplied evidence correctly40%
- passAddresses the actual decision95%
- passRespects explicit constraints46%
- passIdentifies material uncertainty100%
- passAvoids unsupported claims80%
- passProduces the required deliverable86%
- passTalks to the right people100%
- passCoaches first-time interviewers100%
- passDesigned to falsify95%
- passAsks what people did, not what they think94%
- passDoesn't lead the witness89%
- partialMarks what to cut if the call runs over53%
Run
- Run
- #1
- Time to output
- 42 s
- Submitted
- 30 Sept 2026