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4 non-confrontational ways to get your overdue invoices paid

Don't let your shyness get in the way of getting paid!

One of the most infuriating (but also vitally important) things we have to deal with as freelancers and business owners is getting paid. Can you imagine if an employer just… forgot to pay you? I’m sure it’s happened, but it’s SO rare in the world of employment that chasing our earnings isn’t something that we’re typically used to.

Add in a dose of good ol’ imposter syndrome, and you have a recipe for dancing on eggshells, trying not to upset your client just so you can – oh, I don’t know? – eat and pay your goddamn bills?

Dealing with late payments is an absolute must if you’re going to survive, but you don’t have to play “bad cop” with your clients and ruin your professional relationship with them to get paid (at least, save that for a last resort). Over the years, I’ve found a few… “gentle nudges” which usually get the job done.

(I’m certainly not saying these are the only “polite” ways to get paid, but they’re some of the easiest methods for while you’re still on your confidence-building journey. It’s hard to shine when you can’t pay your electricity bill, y’know?)

Before you continue – it’s only fair to let you know that some of the links in this post may be affiliate or sponsored links, so if you click on them and sign up for their service, I could earn a small commission.

C’mon, let’s get you paid already!

1. The “Is everything ready to go, as agreed?” phone call or email

You can do this one even before your invoice is due since it’s not actually a request for payment but more of a reminder that they’ve made an agreement to pay you. And if the invoice’s due date has passed, it works just as well with a payment that is only slightly late if you don’t want to seem “too pushy”.

You could say something like this:

“Hey, I just wanted to make sure you were happy with the terms of our agreement and the proposed timeline and to make sure all the details on the invoice are correct – do you need me to tweak the billing info for your records?”

Obviously, modify a little if you’re selling a physical product: “Hey, just checking your order arrived safely and everything was in order with the shipping and billing?”

At this point (unless they’re really ballsy and say, “Well, you could knock off a zero if you like!” – FYI: you can safely assume this is a joke, just laugh politely and ignore it), they’re likely to tell you that everything is fine, or if there is an issue, you’ll get a jump on it right away: Is a stakeholder taking some unexpected time off that they’ve not told you about yet? Are they confused about the payment plan you’ve offered? Was their order delivered to the deli down the street by mistake?

Consider this an opportunity for proactive troubleshooting. You’re not pestering them – you’re following up. If you make it a charming customer service experience, you can build trust and demonstrate your value, and they won’t even realise they’ve been delicately reminded about their outstanding bill.

Robots are just doing their job image
You can’t blame a robot for doing its job, right?

2. The “automated” overdue invoice email reminders

Before I used FreeAgent, I used to do this a lot. It felt super awkward sending a message that amounted to: “Heeeey, you owe me money, pay me please!”. Because it’s a written medium, it can easily come across as stuffy and abrupt, so… why not make it that way on purpose?

Except you’re not being stuffy and abrupt. Your billing system is!

The trick here is consistency – make sure your signatures, formatted styles, and wording/structure are roughly the same every time:

“Hi [their full name],

Your invoice #[insert the invoice number] dated [invoice date] is now overdue by [number of] days. Please ensure your payment is made promptly using the details provided on the invoice to avoid [late fees/delays to your project/a visit from Pay-up-Pete (delete as appropriate)].

Kind regards,

[your first AND last name – formality is key!]”

Use a typical subject line like “Invoice #[invoice number] overdue reminder”, proofread and double-check it’s grammatically correct (that’s a dead giveaway), and attach a copy of the invoice to the email (seriously, invoices get “lost” all the damn time, so make it effortless to find), and, if possible, schedule the email for a top-of-the-hour send time.

You can save this as a template and reuse it as much as you like. In fact, it’s better if you use precisely this email (update for the number of days overdue, naturally) every time, and send it every few days, as regularly and shamelessly as possible. You know… the way a robot would!

Voila! You now have a non-confrontational “pay me now, damnit!” email that you can detach yourself from emotionally and just get-’er-done. One more thing off the list, and you didn’t even have to be – or speak to – a human. Bliss!

If you want to save yourself the hassle and set yourself up for some really nifty automation, I highly recommend FreeAgent – it’s perfect for freelancers and small businesses and rolls all of your invoicing, bookkeeping, bank statements, tax returns, and financial forecasting all into one easy to use platform. It even integrates with Stripe and GoCardless for flexible payment options for your clients (see steps 4 and 5 below!).

3. The “proof-of-life” phone call

Ew, a phone call. But again, you’re just checking up on them. They might have been busy or had the flu, or got a new puppy that won’t stop cocking its leg at the modem router. Hopefully, they have a good reason, and whether or not that’s the case, you can generally prompt an “oh shit, I need to pay that” moment of clarity like this:

“Hi there, [first name – friendly, right?], I just wanted to make sure you were alright, as I haven’t heard from you in a little while in relation to your account. Is everything okay for you?”

At this point, they’ll either admit they just forgot, inform you that they’re overwhelmed by grief over someone’s death (you just kind of have to assume they’re being honest with that one), or they’ll sheepishly blame it on their chipper but unfortunately not-terribly-bright admin assistant, Paula. (Don’t feel bad for Paula, though – I bet she’s still getting paid on time.)

In any case, unless they state their clear intention of paying it very soon (like, today), you’ll need to encourage them a bit:

“I don’t want to add more pressure, but would you know roughly when you’ll be able to make a payment, so that way I can keep an eye out for it and make sure it’s gone through alright?”

Yes, it’s a little nudge, but you’re still helpful!

You’re making sure their precious pennies are going where they’re meant to. You’re helping to ensure their account is in order. You’re even offering for them to set their own “payment due” date. Generous customer service, indeed!

Luckily, they’re not likely to say, “Oooh, I don’t know… three weeks next Wednesday?” because they’ll know they’re taking the Mick. The only reasonable thing they can say is an equivalent of “as soon as humanly possible” because they’re in your debt, and they know this. People are often subtly inconsiderate through carelessness, but rarely willing to confess their desire to take advantage of you.

It’s hard for them to be difficult with you when you’ve just called to ask if they’re alright.

Remove objections (and therefore delays) by making the process as easy and “win-win” as possible.
Remove objections (and therefore delays) by making the process as easy and “win-win” as possible.

4. The “Would you like a different payment method?” offer

You’ll be tempted to email this one – but don’t if you can help it. This is their last chance to offer a reasonable excuse, and you want them to commit to a specific action instead. People are more likely to do this when you have them on the spot because they’ve just picked up the phone – but if it’s an email, they’ll take all the time they want, leaving you with neither a reason nor a paid balance.

Here we go, then:

“Hi, I’m just checking in to see if you need any help with paying your invoice. If you’re having issues, would you like to try another payment method that’s more convenient for you?”

This one requires a teensy bit of preparation in the form of having another payment method available to them if they say, “Yes, let’s do that instead!”:

If the usual method is bank transfer, also consider offering card payments (such as via Stripe), or PayPal. While there’s a processing fee (and sometimes a delay before the funds finally reach your bank account), you can usually swallow this with the understanding that you’re paying for the convenience of not spending more of your precious, finite days on this good earth chasing an invoice.

Again, you can frame this as a helpful courtesy call, as opposed to a “how dare you haven’t paid me!” complaint. It often makes for a fairly pleasant interaction, too, since you’re not even calling them out on their impertinence- you’re just asking them if you could make it easier for them to stop being, well, rude.

Some people don’t like banking apps and prefer the ease of a card payment. Some people don’t like card payments and would rather use their PayPal account. Some people pay you in far too many £5 notes, and the cashier at the bank will quirk an eyebrow at you and silently assume you’re a stripper. Money is money. Sometimes, the best way to get paid is just to get paid.

5. Prevention tactics: Payment plans and automation

Bonus round!

There’s no guarantee you’ll see all of the money you’re promised (even if you have a Pay-up-Pete ready to break some toes), but you can avoid much of the friction with automated payments.

You’re no stranger to these: Your Netflix subscription, your utility bills, your gym membership that you should probably use/cancel by now. All over the place, other businesses are getting paid promptly and efficiently, and you can, too.

My two favourite services for automated payments are:

  • GoCardless – used for setting up Direct Debit payment plans at regular intervals
  • Stripe Billing – used for repeated card payments (such as subscriptions)

Both have no up-front costs for an account, so they’re easy to access as a small business, and you pay the fees only when you use the service.

You deserve to get paid on time – every time

These steps are only the beginning and are “diplomatic” tactics I’ve used to ease myself into a more assertive financial stance. I still use them with as much compassion as possible, but these are sales agreements and financial boundaries like any other – if they’re not respected, you’ll eventually need to draw a line. When and how will depend on your situation, but you should prepare yourself to draw a line somewhere, at some point, in case it’s do-or-die for your business.

If you’re timid about chasing late payments and feel like a wee orphan asking for more gruel, make no mistake: you are a business owner, and cash flow is the lifeblood of any business. Yours is no exception.

Just because you may have more flexibility with your work than the average employee, you still have the added burdens of finding new clients, managing your schedule and finances, and shouldering the responsibility of your business’s future success.

That’s not “easier” or any “less worthy” of a fair and punctual income.

You work damn hard and deserve to get paid, on time, every time, for your work. It does get easier to chase late-paying clients without fear, shame, or self-doubt. The more you practice, the more your confidence will grow, and the healthier your business’ cash flow will be as a result.

P.S. If you’ve been reading this thinking, “Hey! Wait a gosh-dang minute… she’s used these cheeky methods on me!” Well, yeah, and maybe you should’ve paid me on time. Geez. 😅

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