The end of the year is busy enough without chasing money you’ve already earned. But if you let unpaid invoices slide into the holiday period, you could find yourself starting the new year with a cash flow gap you didn’t plan for. Customers wind down, businesses close, and getting paid becomes harder – not impossible, just harder.

The good news? A bit of EOY housekeeping now can give you a much clearer picture of what’s coming in and when. It’s not about hounding customers, it’s about knowing where you stand. Here are nine practical strategies to help you get on top of outstanding payments before the break.

Review your outstanding and overdue invoices

Start with a clear picture. Pull up your invoices and separate them into two groups: those that are outstanding (sent but not yet due) and those that are overdue (past their due date). For each one, note the amount, the customer, and how long it’s been outstanding.

A small design studio might find they have three invoices overdue by more than 30 days – together worth several thousand dollars. A plumbing business might discover that a handful of small job invoices have slipped through the cracks. You can’t follow up on what you can’t see, so this first step is essential.

Send completed invoices promptly

If you’ve finished work but haven’t sent the invoice yet, now’s the time. The faster you invoice, the faster you’re likely to get paid. It sounds simple, but it’s one of the most common reasons payments are delayed – the invoice simply hasn’t been sent.

A tradesperson who completes a job on a Friday but waits until the following week to invoice is adding days to their payment cycle. A consultant who delivers a report and holds off on invoicing until month-end is doing the same. Send invoices as soon as the work is done, and make sure all the details are correct the first time so there’s no back-and-forth.

Follow up customers before holiday closures

Timing matters. If you wait until late December to follow up on an overdue invoice, your customer may have already closed for the holidays, and your payment could slide into January. Reach out now, while businesses are still operating and people are at their desks.

A quick, friendly email or phone call is usually all it takes. Something like: “Hi [name], just a quick reminder that invoice #123 for $X is now overdue. If you could arrange payment before the holiday break, that would be much appreciated.” Keep it polite, clear, and easy to action.

Check payment terms and expected payment dates

Do you know what payment terms you’ve set for each customer? If some have 7-day terms and others have 30-day terms, it’s worth mapping out when each invoice is actually due. This helps you prioritise your follow-ups and predict when money is likely to land.

A catering business might have a mix of upfront deposits and 14-day terms for final balances. A building supplier might have some clients on 30-day accounts and others who pay on delivery. Knowing the terms for each invoice means you can forecast your incoming cash more accurately and follow up on the right ones at the right time.

Make it clear to customers how and when to pay

Make paying you as easy as possible. Does your invoice clearly show your bank details? Does it state the due date prominently? Is there a link for online payment if you offer one? If a customer has to hunt for payment information, you’re adding friction – and friction delays payments.

A retail supplier might include a “Pay by [date]” line at the top of every invoice, along with clear bank transfer details. A freelance graphic designer might add an online payment option so clients can pay instantly from their phone. The easier you make it, the faster you’re likely to see the money.

Send reminders for invoices that are nearly due

Don’t wait until an invoice is overdue to follow up. A gentle reminder a day or two before the due date can prompt customers to pay on time – many simply forget or let it slip, and a friendly nudge is often all they need.

This can be as simple as a short email: “Hi [name], just letting you know invoice #123 is due on [date]. Let me know if you have any questions.” It’s not pushy, it’s helpful. And it can significantly reduce the number of invoices that slip into overdue territory.

Offer a payment plan for larger overdue amounts

If a customer owes a significant amount and is struggling to pay it all at once, offering a payment plan can be a practical way to get some money in rather than none. Breaking a large invoice into a few smaller payments over a set period can make it manageable for them and bring cash into your business sooner.

A construction business might agree to split a large outstanding invoice into three weekly payments. A marketing agency might offer a client the option to pay half now and half in January. The key is to agree on the plan in writing and confirm the dates, so there’s no ambiguity on either side.

Keep a record of all follow-ups

When you’re juggling multiple invoices and customers, it’s easy to lose track of who you’ve contacted and when. Keep a simple log – a spreadsheet or even a notebook – recording each follow-up: the date, the method (email, phone, text), and the customer’s response.

A bookkeeping business might note that they emailed a client on 1 December, followed up by phone on 5 December, and the client promised payment by 10 December. Having this record means you know exactly where things stand and can follow up again if needed without repeating yourself.

Consider cash flow management software to help with keeping records.

Understand what income may still be outstanding heading into January

Once you’ve reviewed, followed up and recorded everything, step back and look at the full picture. How much money is still outstanding? How much is likely to come in before the break, and how much will carry over into January?

Download our free cashflow forecast template.

Know what’s coming in

It’s not about chasing customers, it’s about knowing what’s coming in and when. When you have a clear picture of your outstanding invoices, you can plan with confidence.