How to Communicate with Potential Late Payers

The most pleasant feeling a business owner or a freelancer can experience in terms of business is getting properly paid after a completed project.

However, many entrepreneurs witness late payments.

The key issue with payments made past the due date is that the business in question needs to find a way to finance their own obligations during that period.

This may lead to lower cash flow, delays in paying their workers and associates and other inconveniences. So, it’s vital for every business to ensure that they charge their services timely.

This is why we’ve prepared six handy strategies that will teach you how to deal with payment-seeking correspondence.

Setting the rules at the beginning

Every business collaboration starts with negotiations. And here’s where you should set the rules that will affect that entire collaboration, all the way to the payments.

Therefore, far-sighted business people will know how to negotiate the terms of such an agreement, so that they protect themselves in advance.

Nevertheless, if you’re still trying to find your way to business success, you might need some help in reaching such a self-protective deal. In order to do that, you should apply the following tactics:

  • Give a precise estimate – Always give yourself more time than necessary to finish a project or a milestone (this can vary from 10% – 30% on top of your initial estimation). That way, you won’t miss any deadlines. As a result, your client won’t have a reason to postpone their payments. On the other hand, if you have more associates working on the same project, ask them to follow suit and include more time than necessary for their share of work, as a time-backup.
  • Divide projects into milestones – When you break a business task into several smaller parts, i.e. milestones, it will force both you and your client to fulfill your promises and put your deals to practice. What makes this strategy perfect is the option to suggest sending invoices and making payments after every milestone.
  • Determine the invoicing pace – You need to tell each and every client what invoicing and payment pace you prefer. For instance, you can establish a 15- or 30-day invoice-payment rhythm and ask your client to stick to it. If that pace can follow the pre-set milestones, you’ll make a great agreement.

Leaving out unnecessary details

If you don’t get paid by the due date, you shouldn’t immediately jump to any negative conclusions.

Business owners might not have even received or seen your email with the invoice. Sometimes email services redirect valid messages to the spam folder. It’s not a common thing, but it happens.

Moreover, some other times business owners or their assistants might simply miss some emails.

Also, if you clutter your invoice emails with too many details, the receiver might overlook the payment details. Therefore, make your payment-requesting emails as straightforward as possible.

That way, the subject of the mail should contain the reason why you’re sending the message.

For example, you can apply the following template: “Company Name, Invoice for MM/DD/YYYY”. Furthermore, the body of the mail should contain a short message saying that you’re sending an invoice for the due payment date. Make sure you attach the invoice to that email or include a direct link to it.

Leave out any other business matters from that particular message (and invoice) and send them in a separate email.

By focusing strictly on the payment-related features, you’ll grasp your client’s attention, which will increase the chance of getting paid on time.

Classy communication

One of the most important features that will make you look more serious is being assertive in business communication.

This means staying determined and decisive in everything you do and say, including your emails pertaining to invoices. However, it doesn’t mean that you should develop aggressive or pushy communication style.

On the contrary, each and every email you send should be written in a careful and polite manner, with a pinch of determination.

Also, don’t make any hasty decisions if you realize your invoice still hasn’t been paid. It’s important to gradually remind your clients about their missed payments.

What you can do to achieve that tone is use proper adverbs for different emails. For instance, if you’re writing the first reminder email after the payment due date, you can formulate your dissatisfaction by saying:

We sincerely hope we’ll receive our payment until MM/DD/YYYY.

Also, if your first reminder letter doesn’t get a proper reaction, you should intensify your adverbs. That way, if your client doesn’t make their payment after the next reminder, you can go with something like:

Your payment needs to be paid by MM/DD/YYYY. Unfortunately, we’ll have to file a lawsuit if you don’t meet our request.

The adverb “unfortunately” expresses both remorse and assertiveness to get what’s yours.

The key here is to gradually use stronger words if the previous attempts ended in the gutter.

Avoiding vague formulations

Apart from clear initial communication, assertive language and concise messages, businesspeople should do their best to stay as clear as possible in their invoice and payment reminder emails.

Let’s say that you’ve just started working for a new client and it’s time to reap the first fruits of your labor. What’s vital here is to say to them explicitly by what date you expect to receive your payment.

For example, if your invoice or the email contains the phrase “payment required upon receipt”, it might cause confusion.

The client could understand such a statement the way they prefer it and make the payment in a few weeks’ time, while you might expect the payment the day after the mail is sent.

Moreover, don’t use the phrase “as soon as possible” in your invoice or reminder emails. As you can see, even some set phrases could sound unsettling in a different context, especially related to payments.

So, in order to avoid any possible ambiguity, make sure you call a spade a spade (especially if you’re in the gardening business) and not confuse your clients with unclear requirements. That way, if you tell your client in your first invoice “Please, pay the $2,000 check by July 24”, there will be no room for misunderstanding.

That way, if you tell your client in your first invoice “Please, pay the $2,000 check by July 24”, there will be no room for misunderstanding.

Adding links for swift payments

Clients will pay you faster if you offer them various payment methods. The most convenient thing to do that is to include the links to different payment services in your emails and invoices.

The most convenient thing to do that is to include the links to different payment services in your emails and invoices.

For instance, you can open a Stripe account and connect it with an invoicing system such as Invoicebus. With this setup, all your invoices will contain one-click option to receive payments.

Additionally, you can use a variety of other payment solutions, as well as let your clients pay you via PayPal.

No matter what options you add to your payment fleet, make sure that you include user-friendly links in your regular invoices and reminder emails, so that your clients can pay you in many different ways and as quickly as possible.

Bringing serious measures

If all the aforementioned efforts have come up against a brick wall, your next email, i.e. the ultimate email, will need to contain some serious measures.

Here it’s important that you retain your manners and not lose your temper.

Since the entire correspondence can be used in court in case you decide to file a lawsuit, any threatening or aggressive reactions could be used against you.

So, stay calm, but inform your client about your future steps.

These could include going directly to court or contacting a debt-collection agency, which will legally force the debtor to pay what they owe you.

Also, your client might react differently if they’re contacted by such a business entity.

This is why you could write something like:

We’re sorry to inform you that your debt towards our business has been redirected to a collection company. They’ll contact you for more details.

If your client’s business is still alive, it’s highly likely they’ll contact you immediately after such an email, asking for a settlement.

Nevertheless, don’t bluff with such messages, because you’ll look ridiculous if the other party realizes you didn’t mean it for real.


The entire communication regarding invoices and payments requires utter seriousness and determination from the very beginning.

If you bring your own set of rules in advance and present them to each and every client, it’s highly likely you’ll experience fewer issues with late payments.

Still, there will always be clients who can’t pay you on time.

This is where our tactics will help you write emails and invoices that will ensure getting paid on time while showing respect to your debtors.

Only such an honest but decisive payment policy will ensure straightforward collaboration with clients and steady business development.

Mark Thomasson
Mark is a biz-dev hero at Invoicebus - a simple invoicing service that gets your invoices paid faster. He passionately blogs on topics that help small biz owners succeed in their business. He is also a lifelong learner who practices mindfulness and enjoys long walks in nature more than anything else.
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