Aged receivables is the report to start from. The assistant reads it, sorts it, cross-references who actually pays on time, and drafts the reminders. What it does not do is send anything on its own. Every send is a separate, explicit confirmation in the conversation, one document at a time. That gate is the reason this is safe to point at real customers.
Start with the aging, then immediately leave it
"Pull aged receivables as of today, grouped by customer, oldest first."
You get the usual buckets: current, 1 to 30 days, 31 to 60, 61 to 90, over 90. Useful, and available in QuickBooks too. The prompt that is not available in QuickBooks is the next one:
"For everyone past 30 days, list the individual invoices with due date and days late, and tell me when that customer last paid anything."
Now the aging is a list of decisions instead of a total. The detail report holds the invoices, the payment history holds the pattern, and asking for both in one question is the whole point.
Genuinely late versus always late
These are two different problems and they need two different emails.
"For each customer with something overdue, work out their average days to pay over the past year and compare it against their terms."
A customer who has paid at 45 days on net 30 terms, every time, for three years, is not a collections problem. They are a terms problem. You change the terms, price the float in, or stop looking. A customer who has always paid on time and is suddenly at 62 days is a different signal, and that one deserves a phone call rather than an email.
Two questions worth asking before you write a word:
"Is any of this already partly paid, or does it have an unapplied credit sitting against it?"
"Do any of these customers have an open estimate or work in progress right now?"
Chasing an invoice that a credit memo already covers is how you lose a customer over 400 $.
Drafting the reminders
"Draft a reminder for each customer past 45 days. Polite, three sentences, invoice number, amount, original due date. For the one we spoke to last week, acknowledge that call."
You get the drafts in the conversation. Read them. They will be reasonable and slightly generic, and the customer-specific sentence is the one you will rewrite. That is fine. Writing the first version of five near-identical emails is the tedious part, not the skilled part.
Tone is worth being explicit about, because the default is softer than most people want by day 60:
"Redo the ones past 90 days. Same facts, no apology, and ask for a payment date rather than a payment."
Nothing leaves without a confirmation
The gate is not a setting you can leave open:
- Every connection starts read-only. On a read-only company nothing can be created, changed, or sent at all, so you can do the whole reading and drafting exercise before you ever grant more.
- With full access enabled, emailing an invoice still requires an explicit confirmation for that specific document, in the conversation, every time.
- Voiding and deleting work the same way.
So the realistic flow is: read the aging, draft, edit, then confirm each send. If you would rather copy the drafts into your own inbox and send them from there, do that. Plenty of people should, if only because replies land where you already read them. The security page covers the access model in more detail.
The pattern under the panic
"Over the last twelve months, which customers were consistently late, and what does that add up to in days of cash tied up?"
This is the question that changes something. Chasing is symptomatic treatment. Deposits up front, shorter terms for the repeat offenders, and dropping the customer who is permanently at 70 days are the actual fixes, and you need a year of pattern to argue for any of them.
Where this is the wrong tool
You invoice a handful of customers a month. QuickBooks has automatic payment reminders built in. They are free, they run without you, and a process that fires on its own beats a better process that needs you to start a conversation.
Collections is a real function at your company. Dunning ladders, escalation rules, promise-to-pay tracking, thousands of open invoices: buy a receivables tool. This is an assistant reading a report, not a system of record for collection activity.
You are on QuickBooks Desktop. Not supported, structurally. The API is Online only.
If you have not connected a company yet, start here. Everything above except the sending works on the read-only access that every connection starts with, which makes chasing invoices a good first week task.