with the skill
# Review of your interview questions
Only #5 is a good question as written. #2 is fine with a tweak, and the other four would give you misleading data.
| # | Verdict | Problem | Fix |
|---|---|---|---|
| 1 | Rewrite | Leading and closed. It tells them what to feel, and they'll say "yes, so frustrating" to be agreeable. | "Tell me about the last time a client paid you late. What did you do?" |
| 2 | Tweak | Fine, but vague. People estimate badly. | "Walk me through the last few invoices you sent. How many in the past 3 months? How did each get paid?" |
| 3 | Cut | Hypothetical future behavior plus a price pitch. People say yes to "would you pay" and then don't. | Ask about current spend: "What do you pay for today to manage invoices or payments? Have you ever paid for something to get paid faster?" |
| 4 | Cut | It's a pitch, and it invites compliments ("sounds cool!"), which are noise. | "What have you tried to get paid faster? How did your clients react?" |
| 5 | Keep | Specific, past-tense, and story-based. This is your best question. | Add follow-ups (below). |
| 6 | Cut | Leading, and a 1-10 "hate" score tells you nothing actionable. | "Which admin tasks do you tend to put off? When did you last put one off, and what happened?" |
## Follow-ups to add to #5
- "What happened next?"
- "How late was it, and how much was the invoice?"
- "How did you follow up? How long did that take?"
- "What did it affect, such as rent, other bills, or your stress level?"
- "How did you feel about reminding them?"
- "Did it change how you work with that client?"
Show the rest (40 more lines)
## What's missing
- **Existing solutions.** FreshBooks, QuickBooks, Wave, and PayPal already send reminders. Ask what they use now and why it does or doesn't work.
- **Relationship risk.** Many freelancers avoid chasing because they fear damaging the client relationship. This could decide whether your product works, so explore it without leading: "How do you decide when and how to follow up?"
- **Frequency and severity.** How often are payments late, by how much, and what does it cost them? A freelancer with one late invoice a year isn't your customer.
- **Workarounds.** Calendar reminders, spreadsheets, and templated emails all show real pain.
- **Screening.** Confirm they've had a late payment in the last 6 months, or you'll get opinions instead of experience.
## Suggested flow (about 30 min)
1. **Opening (2-3 min):** "I'm here to learn, not sell. No right or wrong answers. OK to record?"
2. **Context (5 min):** "Tell me about your freelance work. What does a typical week look like?" Then Q2.
3. **Core (15-20 min):**
- Q5 with follow-ups
- "What tools or methods did you use to follow up?"
- "What's the hardest part of getting paid?"
- "What have you tried to fix this? What happened?"
- "What does a good payment process look like for you?"
- "What do you spend on this today, in time or money?"
4. **Wrap-up (3-5 min):** "Anything I didn't ask that matters?" and "Who else should I talk to?"
Don't mention your product or its price during the interview. If they ask what you're building, say "I'll tell you at the end."
## Note-taking template
```
Participant: [Name / ID]
Date:
Key Jobs: [What they're trying to accomplish]
Current Solution: [What they use today]
Last late payment: [Amount / how late / what they did]
Biggest Pain: [Their #1 frustration, in their words]
Relationship concerns: [Fear of chasing clients?]
Desired Outcome: [What success looks like]
Willingness to Pay: [Current spend in time/money, past attempts to solve it]
Strong emotions: [Where and about what]
Surprise Finding:
Follow-up:
```
Listen for specific stories, workarounds, and money or time already spent. Treat compliments and "I'd totally use that" as noise.
If you tell me the interview length and who you're recruiting, such as solo designers versus consultants, I can tailor the full script.