Why chasing invoices is so unpleasant (and why most people do it wrong)
Chasing invoices feels uncomfortable because it's personal. You've done the work, you're owed the money, but you still feel like you're the one imposing by asking for it.
So most people avoid it until they really have to, which means by the time you follow up, the invoice is 30+ days overdue and the conversation is already awkward.
The fix isn't to be more assertive. It's to automate the follow up so it happens consistently and professionally, without you having to be involved, and without it feeling like a confrontation.
When an automated system sends a reminder, it doesn't feel personal to the client. It feels like admin. Which is what it is.
The automated invoice follow up sequence
Here's the sequence we build for clients. Every step is automated: you don't touch it unless a client needs genuine escalation:
Tone matters, especially in South Africa
South African business culture tends to value relationships. The tone of automated reminders matters: you don't want to sound like a foreign debt collector the moment something is a day late.
We design the sequences to escalate gradually. The first few messages are genuinely friendly, they could easily be read as a helpful reminder rather than a demand. Only after multiple days overdue does the tone become firmer.
You can personalise the language to match your business voice, whether you're more formal (legal, financial services) or more casual (trades, creative industries). The same logic applies regardless of tone.
What you need to set this up
- Accounting software: Xero, Sage, QuickBooks or similar. Most have webhooks or APIs that trigger when an invoice is created or updated.
- A payment gateway: PayFast, Peach Payments or Yoco for the payment links. Their webhooks trigger when payment is received.
- Make.com or Zapier: the automation platform that connects everything and manages the sequence logic.
- WhatsApp Business API: for the WhatsApp reminders. Email only versions can be done without this.
If you're not currently using accounting software (still managing invoices in Word or Excel), this is a good moment to upgrade. The automation savings alone pay for a Xero subscription within weeks.
What about POPIA?
Sending automated reminders to clients is generally fine under POPIA. You have a legitimate business purpose (collecting payment for services rendered), and the communication is directly related to the existing business relationship.
You should include an easy way to update contact preferences, and you shouldn't share client data with third parties without consent. Standard good practice applies.
Get this set up for your business
We build automated invoice follow up systems for South African businesses. Book a free audit and we'll review your current billing and payment process and show you exactly what needs to change.