By KYN AI Advisory Team — AI implementation specialists, Singapore
Chase an unpaid invoice three times: at 3 days overdue with a friendly reminder, at 14 days with a firm request and a named payment date, and at 30 days with a call from a person and a clear next step. This is the schedule we run on KYN's own receivables. Each touch has one job, a fixed tone and an owner. The schedule works because it removes the decision of whether to chase. The calendar decides.
Why a fixed schedule beats chasing when you remember
Overdue invoices are rarely disputes. They are usually a missed approval, a wrong purchase order number, or an invoice sent to the wrong person. A prompt, polite message fixes most of them. The cost of waiting is that the invoice drops down the customer's list, and the friendly tone becomes harder to justify.
Founders delay for three reasons: they do not want to damage the relationship, they are busy, and they cannot tell who has paid. A schedule answers the first two. A clean reconciliation answers the third.
What is the 3, 14, 30 day schedule?
Days are counted from the due date, not the invoice date.
| Day overdue | Channel | Tone | Goal | Owner | |---|---|---|---|---| | 3 | Email | Friendly | Confirm receipt, surface blockers | Finance, with a draft ready | | 14 | Email and WhatsApp | Firm | Get a payment date in writing | Finance | | 30 | Phone call, then email | Direct | Agree a plan or escalate | Account owner or director |
Some teams add a day -3 courtesy reminder before the due date. It is optional. Start with the three above.
What do you say at each step?
Day 3: the check-in
Subject: Invoice [number], due [date]
Hi [name], our records show invoice [number] for [amount] was due on [date]. I have attached a copy. Could you confirm it has been received and let us know the expected payment date? If anything is blocking approval, tell us and we will fix it today.
The goal is not payment. It is information. Often the reply is "forwarded to accounts" or "need a PO number". Both are solvable.
Day 14: the firm request
Subject: Invoice [number], now 14 days overdue
Hi [name], invoice [number] for [amount] is now 14 days past its due date of [date]. Please confirm the payment date by [two working days from now]. The payment details are below. If there is a dispute, tell us what it is and we will resolve it.
Two changes from day 3: a deadline for a reply, and the word "dispute" invites any objection into the open.
Day 30: the call
Pick up the phone. Say: "I want to agree how and when invoice [number] gets paid." Then do one of three things:
- Agree a payment date and confirm it by email within the hour.
- Agree a part payment and a date for the balance.
- Learn the real reason and assign who fixes it.
If the customer will not engage, the account owner or a director decides the next step: pause new work, stop supply, or move to a formal demand. Do not let the day-30 step be the first time a senior person hears about it.
What should you check before sending any chase?
A wrongly sent reminder costs more goodwill than a late one. Run these checks first, every time.
- Has the payment arrived? Check the bank feed or the latest statement, not just the ledger.
- Is there a partial payment? Chase the balance, and say so.
- Is there a credit note, dispute or hold? Do not chase a disputed amount with the standard text.
- Is the contact right? Send to accounts payable, with the buyer in copy.
- Is the invoice correct? Missing PO numbers and wrong entities cause a share of delays. Fix and resend.
This is where bank matching pays off. If the ledger cannot tell who has paid, you either chase customers who paid or stay silent with those who did not. Our notes on automating bank reconciliation in Singapore and Xero bank feeds versus automated reconciliation cover the matching step.
How do you handle special cases?
- Large customers with long approval chains. Ask on day 3 for the name of the approver and the payment run date. Chase against that date.
- Instalment contracts. Treat each instalment as its own invoice with its own clock.
- Repeat late payers. Move them to shorter terms or a deposit. The schedule diagnoses; terms are the cure.
- Overseas customers. Account for time zones and bank holidays. Quote the currency and who bears bank charges.
- Sensitive relationships. Let the account owner send day 3 and day 14 in their own words. Keep the timing; change the author.
What should be automated, and what should not?
| Step | Automate? | Why | |---|---|---| | Spotting an invoice that is 3, 14 or 30 days overdue | Yes | A date calculation | | Checking the bank feed for payment | Yes | A match against data | | Drafting the message | Yes | Fixed text with fields | | Sending the message | Wait for a person, at least at first | It carries your name and affects a relationship | | Logging the chase and the reply | Yes | Builds the history | | Reading the reply and labelling it (promise, dispute, wrong contact) | Yes, with review | Saves reading time | | Deciding to stop supply or demand payment | No | Commercial and legal judgement |
A common pattern is a daily queue. Each morning the finance lead sees the drafts due that day, with the invoice, the bank check result and the history. One click approves or edits. A queue of ten takes a few minutes.
How do you measure whether it works?
Track four numbers monthly.
- Days sales outstanding (DSO). Receivables divided by credit sales, multiplied by the days in the period.
- Percent of invoices paid within 7 days of due date.
- Overdue balance older than 30 days, in dollars and as a share of receivables.
- Chases sent in error: reminders to customers who had already paid. The target is zero.
If DSO falls and the error count stays at zero, the schedule works. If errors appear, fix the matching before increasing volume.
Where KYN fits
This is the schedule we run on KYN's own books: receivables chased at 3, 14 and 30 days, with a reply desk that sorts each answer. For an insurance brokerage, the reply desk sorts replies at about S$0.01 each. Outbound messages wait for a named person, every action is logged with the actor, and the system runs in a cloud account in your name.
The first 14 days are a review of your stack and interviews with your team. A full build ships in under 90 days. See finance systems and operations.
Frequently asked questions
Should I charge late payment interest?
Only if your contract or terms say so. State the rate and the trigger in the terms before the sale, not in the day-30 email. Many SMEs keep it as a right they rarely exercise, because the relationship matters more than the interest.
Is WhatsApp acceptable for payment reminders?
For many Asian markets, yes, and replies are faster than email. Use it for the day-14 step with an email copy, so there is a written record the customer's finance team can forward.
When should I send an invoice to a collection agency?
After the day-30 call fails, the customer has stopped replying and any dispute is resolved. Check the contract and get legal advice before sending a demand, because the wrong step can damage a relationship you may want to keep.
Checked 30 October 2026.
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