The reason it feels awkward is that you are treating the money as a favour to ask for. It is not. You did the work under terms both of you agreed, and payment is part of those terms. Every template below is written from that footing, which is what makes them comfortable to send.
Send something earlier than feels comfortable
The most common mistake is waiting. Two weeks of silence turns a one-line message into a difficult one, because now you have to account for the gap as well as ask about the money. Say something the day after it is due, while it is still small enough to be nothing.
The second most common mistake is sending the same message five times. If two polite reminders have not worked, a third polite reminder will not either. Each stage below does something different: the first assumes an oversight, the third asks a question that needs answering, the fourth states a position.
The four messages
Replace anything in [brackets]. Keep them short. A long chase reads as an apology for chasing.
Three days before it is due
Optional, and the highest-value message you will send
Nothing is late yet, so there is no awkwardness at all. This one exists to stop the problem happening.
Subject: Payment due Friday, anything you need from me?
Hi [name], Quick heads up that [reference] is due on [date]. If you need anything from me to get it processed, a PO number, a different contact, a copy of anything, just say and I will send it over today. Thanks, [your name]
A few days late
Day 3 to day 5
Assume they forgot, because they usually did. Give them an easy way to fix it without either of you addressing it directly.
Subject: Re: [reference]
Hi [name], Just circling back on [reference] for [amount], which was due on [date]. I suspect it has slipped through. If it is already in your next payment run, ignore me and apologies for the nudge. Thanks, [your name]
Two weeks late
Day 14
Two reminders have not worked, so stop repeating and start asking a question they have to answer. A date is the ask, not the money.
Subject: When can I expect payment on [reference]?
Hi [name], [reference] for [amount] is now two weeks past its due date and I have not heard back. Could you let me know what date it is scheduled for? If there is a problem with the invoice or the work, I would rather know so we can sort it. Thanks, [your name]
A month late
Day 30
State your position plainly and without threat. You are not asking for a favour and you do not need to pretend otherwise.
Subject: [reference], overdue 30 days
Hi [name], [reference] for [amount] is now 30 days overdue and I have chased three times without a reply. I would like to get this resolved directly rather than escalate it. Can you confirm a payment date this week? For reference, UK law entitles me to statutory interest and a fixed sum on late commercial payments. I would prefer not to apply either, and I am not doing so yet. Thanks, [your name]
What not to do
- Do not apologise for asking."So sorry to chase" tells the reader you think you are imposing, and invites them to agree.
- Do not explain your cash flow. It shifts the reason for paying from their obligation to your hardship, which is a weaker position and an uncomfortable one to be in.
- Do not threaten anything you will not do. Mentioning legal action you have no intention of taking is the fastest way to be ignored by someone who has seen it before.
- Do not go quiet after the last reminder. This is where most money is actually lost. The schedule ends, nothing replaces it, and the amount simply ages.
When politeness has run its course
Past thirty days you are no longer dealing with an oversight. UK law entitles you to statutory interest and a fixed sum on late commercial payments, and you do not have to go to court to be entitled to it. Work out what you could claim before you write that message. Knowing the number changes how the message reads, even if you never mention it.
Common questions
Is it rude to chase an invoice?
No. You did work under agreed terms and payment is part of those terms. Chasing is administration, not a favour you are asking for. The discomfort most people feel comes from wording that treats it as a favour, which is what the templates here are designed to avoid.
How long should I wait before chasing?
Send something the day after it is due. Waiting a fortnight to say something makes the eventual message harder to write, not easier, because you then have to explain the delay as well as ask for the money.
What if chasing damages the relationship?
In practice a client who pays late and is asked about it politely almost never leaves over the asking. A client who would leave because you asked to be paid for work you did was not a durable client. The larger risk is the reverse: quietly resenting a customer you never actually spoke to.
Should I mention interest and late payment fees?
Not early, and mentioning your entitlement is different from applying it. Around day 30 it is reasonable to note that the entitlement exists while making clear you would rather not use it. That framing often moves a payment on its own.
Should I phone instead of emailing?
For anything significant, yes, and sooner than feels comfortable. A two-minute call at day 14 resolves more than four emails. Email after the call to confirm what was agreed, so there is a record.