User interview — freelance bookkeeper, invoice reminders
A freelance bookkeeper with 14 small-business clients explained how he chases unpaid invoices every week and why he wants to approve reminders before they are sent.
Summary
Robert manages invoicing for 14 small businesses, mostly tradespeople. Every Monday he exports unpaid invoices to a spreadsheet, because the overdue list in the app can’t be filtered by client. Reminder emails go out by hand: he worries that automatic reminders would upset his clients’ best customers, who are often only a few days late. He would pay for reminders he can review and approve in one batch, and asked for read-only access for each client.
Participants
- Nina Alvarez — product researcher, leads the interview
- Robert Hale — freelance bookkeeper, 14 small-business clients
Agenda
- Background and clients
- How unpaid invoices are tracked today
- Reminders
- Wishes and ideas
Action items
| Owner | Task | Due |
|---|---|---|
| Nina Alvarez | Send Robert the thank-you voucher for taking part | This week |
| Nina Alvarez | Invite Robert to a second session with the reminder prototype | — |
Interviewee profile
Robert Hale, freelance bookkeeper for nine years. Works for 14 small businesses, mostly plumbers and electricians, and sends around 300 invoices a month on their behalf. Uses the app every day on a laptop, rarely on the phone.
Key insights
- Chasing unpaid invoices is a Monday routine that takes about two hours.
- He exports the overdue list to a spreadsheet because it can’t be filtered by client in the app.
- Automatic reminders feel risky: he wants to see each one first, because some late payers are his clients’ best customers.
- Read-only access for clients would save him several emails a week.
Notable quotes
- “Every Monday I export the overdue list and sort it by client by hand.” (6:12)
- “I can’t send a reminder to someone who orders every week — I need to see it first.” (14:48)
- “If I could approve them all in one go, I’d pay for that tomorrow.” (22:05)
Pain points
- The overdue list can’t be filtered or grouped by client.
- Reminder emails are written and sent one by one.
- Clients email him to ask whether a customer has paid, because they can’t check themselves.
Feature requests and ideas
- Reminders prepared automatically but sent only after his approval.
- A filter for overdue invoices by client.
- Read-only access for each client.
Questions and answers
- Q: How do you find out which invoices are overdue?
- A: He exports the overdue list every Monday, sorts it by client in a spreadsheet and works through it client by client.
- Q: What stops you from using automatic reminders?
- A: Fear of upsetting good customers who are only a few days late; he wants to see each reminder before it goes out.
- Q: If you could change one thing, what would it be?
- A: Reminders he can review and approve in one batch.
Next meeting
Second session with the reminder prototype — date not set yet.