How to chase unpaid invoices (without becoming the bad guy)

The exact wording, timing, and tone that gets invoices paid — without burning the client relationship. Plus what to automate.

The longer you're in business, the more you realise that chasing invoices isn't really about the money. It's about the awkwardness. Nobody wants to be the person sending "just a gentle reminder" for the third time to someone they'll see at a networking event next Tuesday.

But unpaid invoices aren't a rounding error. The UK's average small business has £24,841 tied up in late invoices at any given time, according to Intuit QuickBooks. For a sub-£500k/year business, that's often more than one month of operating cash.

Good news: there's a way to chase reliably that works, doesn't damage relationships, and doesn't require you to be assertive beyond your comfort zone. Here's the framework.

The foundation: send the invoice the same day

Every chase conversation starts with when you sent the invoice. And the biggest lever most businesses are not pulling is invoicing on the day the job ends.

Data from FreshBooks: invoices sent within 24 hours of job completion get paid 30–45% faster than invoices sent a week later. It's not because faster invoices are scarier — it's because the job is still fresh in the client's mind, still on their to-do list, still budgeted in their head.

If there's one change you make after reading this post, make it this one. Send invoices the day the work is done. Everything else in this article gets easier by 10× if you do.

The three-stage chase

The trick with late invoices isn't a single scary email. It's a graduated sequence that escalates in tone but never in volume. Three stages is the sweet spot — most businesses stop at one, some go too aggressive in two.

Stage 1 — Day 7 past due: the friendly nudge

Tone: genuinely warm. Assumes good faith. Never mentions consequences.

Subject: Invoice [number] — just a nudge

Hi [Name],

Hope you're well. Quick heads-up — invoice [number] for [amount] was due on [date] and hasn't come through yet. Totally possible it's just sitting in the "to do" pile — happens to me too. If it's simpler, the payment details are on the invoice attached.

Let me know if there's anything holding it up.

Cheers,
[Your name]

Why this works: you've reminded them without accusing them. You've pre-empted the "oh I forgot" excuse (and validated it — happens to me too). You've made it easy to pay (the invoice is re-attached). You've also opened a door for them to flag any problem ("if there's anything holding it up").

Stage 2 — Day 14 past due: the direct check-in

Tone: still warm, but now you want a response. You're asking a question they have to answer.

Subject: Invoice [number] — can you give me a date?

Hi [Name],

Just following up on invoice [number] for [amount]. It's now two weeks past the due date.

Can you let me know when I should expect payment? If there's a problem with the invoice or the work, I'd rather know so we can sort it out.

Thanks,
[Your name]

Why this works: you're asking for a specific commitment (a date). You're still leaving room for problems. You're not threatening anything, but you're also not pretending this is fine.

At this stage, most of the invoices that are going to get paid will get paid. The remaining ones fall into two buckets: genuine dispute, or client in financial difficulty.

Stage 3 — Day 30 past due: the final notice

Tone: formal. Polite but businesslike. Next step is explicit.

Subject: Invoice [number] — final notice

Hi [Name],

This is a final notice on invoice [number] for [amount], now 30 days past due.

I'd like to resolve this without any formal steps. Can you confirm a payment date by [5 working days from today]? If I don't hear back, I'll need to apply statutory interest and late payment charges under the Late Payment of Commercial Debts Act, and consider next steps.

Regards,
[Your name]

Why this works: you've named the law. You've given them a deadline. You've made the consequence explicit but left a path to avoid it. Most clients at this stage either pay or surface the real problem.

When to break the pattern

The three-stage sequence works for 80–90% of late invoices. But there are cases where you should break it:

• Long-term relationship client: call first, don't email. A 30-second phone call usually resolves what three emails can't.
• Known cash-flow issues on their side: skip to stage 2 or 3, but offer a payment plan. A 50% now, 50% in 30 days arrangement beats a 0% now, 0% in 90 days one.
• New client, first invoice: be slightly warmer than the template above. First invoices often have teething problems (wrong PO reference, wrong email, wrong accounts contact).
• Client going silent: escalate faster. If they didn't reply to stage 1, compress stage 2 and 3 into a single email on day 14.

What to actually automate

The chase sequence above is standardised enough to automate. Most accounting software (Xero, QuickBooks, FreeAgent) has basic "invoice reminder" features — but they're blunt. They'll send the same "your invoice is overdue" email at day 7, 14, 30 regardless of relationship, tone, or context.

The right level of automation is:

• Send the invoice automatically (day-of-completion) — this is the biggest lever.
• Schedule the chase sequence in advance — written in your voice, graduated in tone, sent on day 7/14/30.
• Pause when the client replies — so you don't send stage 3 to someone who's in the middle of a payment dispute with your bank.
• Log everything — so when you're on a call with the client three months later you can say "I sent you an email on the 12th, then a follow-up on the 19th..."

This is exactly what Maestren's Get Paid category does. Invoice sent the day the job ends, chased on the three-stage cadence, paused if the client replies, logged automatically. Nothing forgotten, nothing repeated, nothing awkward.

What not to do

A quick list of chase-email patterns that don't work, in case you were considering them:

• Passive-aggressive "Per my last email..." — signals you're emotional about it. Emotion is leverage the client can use against you.
• Threatening consequences you won't follow through on — "I'll have to take this to court" is fine only if you actually will.
• Cc'ing someone higher at their company — embarrasses the person who was going to pay you eventually. They'll pay you last next time.
• Daily reminder emails — you become spam. They filter you out.
• Emotional language — "this is really affecting our business" — only use if true and the client cares.

The TL;DR version

Send invoices same-day. Run a three-stage chase: friendly nudge on day 7, direct check-in on day 14, formal final notice on day 30. Use payment-plan offers for genuine cash-flow problems. Automate the repeatable parts; handle the relationships yourself.

The clients who are going to pay will pay. The ones who aren't need you to say so firmly once, and then take action. Neither of those conversations has to be uncomfortable if you've set the expectations in writing from the start.