How to Remind Someone to Pay You Without Feeling Bad

Are you owed money by someone and feeling stressed about how to ask for it? This article will walk you through how to remind someone to pay you without feeling guilty about it. Asking for money is never easy. Even if the said money is rightfully yours, you still might feel awkward having to send payment reminders to clients.

Luckily, you don’t have to be the most confident person in the world to successfully remind someone to pay. If you're looking to avoid dealing with outstanding invoices and having to make awkward phone calls, you're in the right place.

How to remind someone to pay you

When you find yourself in a situation where clients owe you money, you need to think before you act.

Before you resort to a phone call or a never-ending amount of messages, think about how you want the conversation to go. You need to be polite but direct. That's the only way you'll get paid.

Payment reminders only work if done right. Otherwise, you'll ruin your cash flow.

Let's take a look at how to remind someone to pay you.

Give them the benefit of the doubt

If this is your client's first time being late with a payment, don’t automatically jump to conclusions. It could be that they just forgot or had an emergency that prevented them from dealing with invoices. 

That’s why your first message should be friendly. Send them a short email reminding them of a previously sent invoice and give them a new deadline for payment. Don't start off by threatening legal action.

This way, your client has an out for why your invoice wasn’t paid. They can easily say that it slipped their mind and pay without making the process awkward for anyone.

On the other hand, if you start off by accusing them of being malicious, they will get offended and it may affect your business relationship moving forward. 

Give them the same amount of respect you would want to receive from them and keep in mind that they are your source of revenue. 

It’s easy to see how a single invoice can slip through the cracks and if that is the case for your client, they will appreciate your friendly reminder. 

Don’t be aggressive when reminding someone to pay you

If you have a good relationship with your client and want to salvage it, you need to keep your cool. Being aggressive will only alienate you from the client and ruin the business relationship. 

The less demanding your approach is (in the early stages of the process), the easier it will be to communicate.

If your first payment reminder message to the client is aggressive and comes with a list of demands, it will give your client pause and they will start to rethink whether this partnership is worth it for them. 

Think about how your message will come across. After all, you want your client to pay and to do it in a timely manner and the best way to go about it is to make the process easy for them. 

You have to make sure your emails and messages are easy to respond to. If you automatically ask for the payment and interest, you’ll make things unnecessarily hard for yourself. 

Payment reminders can still be effective even if they're not rude.

Make sure your approach has enough empathy. After all, not everyone has malicious intent and showing grace in a situation where they owe you money goes a long way. 

Create a clear plan

If your client doesn’t seem cooperative in this process, you might want to bring out the big guns. In order to do so, you’ll need to create a plan. 

The How to remind someone to pay you plan, if you will, needs to focus on a few things:

• How much work (if any) will you be doing until your client pays?
• Who will be communicating with the client moving forward?
• How often will you send reminders to the client?
• Are you going to change the price - to include interest?
• Will you take on more work/clients in the meantime?
• What will you learn from this example?

Make sure to include your team for help recovering outstanding payments

It’s important that you get your team together and explain the situation to them. A lot of companies decide to stop working on any projects associated with clients that are late with payments. 

This decision is completely up to you. However, whatever you decide, make sure to communicate it openly with your team.

Otherwise, your clients may try to undermine you by messaging your employees directly and getting them to do additional work. 

That’s why we recommend that you put an embargo on all communications and make sure you’re the only person talking to the client. 

Make sure to also create a plan on how often you will send reminders to the client. This will depend on your payment plan - are you charging the client weekly or monthly? Once you figure out when is the best time to send your reminders, create a simple template. 

It doesn’t have to be long, nor should you use an emotional plea, just get straight to the point. 

A good example is

Hey [insert name],

Our last invoice still hasn’t been paid. 

Can you please settle the payment in a timely manner?

I’m attaching the invoice below.

Thank you in advance.

Should you add interest? 

This is an interesting question that deserves special attention. The answer to it can be found in the initial contract. Did you outline what happens in a situation like this in your terms and conditions? 

If not, you’ll need to invest a lot more time and effort in the whole process. Make sure to clearly communicate with your client and set boundaries for future business dealings. 

Once you’re already in this situation, you can at least learn from it.

There is a better way

The best way to avoid chasing your clients for payments is by starting the business relationship with a proposal that clearly outlines the roles and responsibilities of both sides. 

If you’re not a masochist, you’d probably want to find a way to create your documents in a quick and easy way.

Say goodbye to creating business proposals from scratch or sending boring PDFs by discovering Better Proposals. We offer more than 80 free proposal templates that you can customize to your needs in minutes. 

Every template comes with a prewritten structure that includes Terms and Conditions. In it, you can write exactly what happens in a situation like this, step by step. Outline your payment terms and provide practical examples.

That way, you can ensure that your clients pay any outstanding invoices regularly since there is a clear outline of the process that comes in place if they don’t. 

Maybe you increase the invoice with every week that passes, stop working on all projects or hinder progress in a different way. The more hypothetical scenarios you cover, the better. After all, small businesses can't afford to have outstanding payments.

This way of thinking will help you never have to remind someone to pay you again.

Stay confident, and don't feel bad about reminding people to pay you

If the process of reminding someone to pay you drags out, you’ll need to prepare for a lot of pushback. The important thing is to keep your head up and stay confident. 

Your approach will have a huge impact not just on your client but also on your employees. If they see you losing your nerve and being stressed out about a missing payment, they’ll start to get anxious. 

Once your team members feel that you’re tense, they will start fearing for their livelihood and in turn, their productivity will go down. Thereby if you stay confident, you can facilitate productive team coordination and boost the productivity level of your team.

That’s why it’s important to explain to them that even if your client misses a few payments, you’ll be good.

Don’t underestimate the effect this could have on your employees and make sure to speak to them anytime something like this happens. 

Be consistent and stand your ground

Stay consistently confident when communication with clients. Don’t let them get to you and make sure you never lose your cool. If you let your clients push you around, they will never pay the invoice. 

When communicating with a client that’s late with a payment, make sure to keep it short and straight to the point and don’t let them lead the conversation. 

Since they’re not paying you, they are not entitled to your time, so make sure to cut them out if they start giving you the same excuse over and over again. 

Not everyone is born with negotiation skills, but you can work on them. The most important thing is to know when to cut the other person off. There is only so much patience you can have for a person that’s avoiding payment. 

If all fails, give a discount

In some instances, dragging out the payment process isn’t worth it. It can be a draining process, and we’re not talking exclusively about money. 

You could save time and effort by giving your client a discount. That way, they will have more incentive to pay and settle the entire deal. 

It may sound counterintuitive since we mentioned interest earlier in the article, but sometimes, the best thing for you is to receive a smaller amount and move on. 

That way, you can start a clean slate, look for new clients and remove a source of stress in your life. With no overdue payments in your way, you can focus on more productive things.

However, if you’re going to use this technique, make sure to put a time limit on it. That will create a sense of urgency and your client will know that you won’t lower your price further. 

Make sure that the time limit isn’t longer than 2-3 days. If you give them more than that, they won’t take the offer seriously. Also, don’t go overboard with your discount. Keep it under 15%. 

Avoid payment reminders by asking for payment upfront

To avoid reminding people to pay you moving forward, once you settle the outstanding invoice, create a different payment plan that ensures you get paid upfront.

That way, you can avoid any hangups and headaches from bad clients. Charging upfront also helps you have a steady stream of revenue, which is crucial for scaling your business. 

Once you have a reliable monthly recurring revenue, you can make predictions about future periods and figure out how much money you can invest, save and use on gaining new leads. 

If you're constantly focusing on the money owed by clients, you won't be productive enough to work on new projects. After all, we're not talking about a few dollars here.

How can Better Proposals help?

If you’re not sure how to change your payment model, you can rely on Better Proposals. Our documents come with an online payment option that lets your clients pay their fees straight through the proposals. 

This means that you don't have to create separate invoices since everything is outlined in the business proposal.

With this feature, you will never miss another payment and you will gain a polite way of explaining to your clients why it’s a necessity for them to pay upfront. 

Since this is so convenient, collecting payment should be a breeze both for you and your client.

The payment option can be set up through PayPal, Stripe and GoCardless, which means that you can set up weekly, monthly or one-time payments, depending on the provider. This effective feature will help you say goodbye to payment reminders.

Since all of the payment details are already lined up it's easy to make the payment happen.

However, Better Proposals isn't just a tool that helps you out if you're owed money.

With our tool, you get much more than proposal creation. We’re here to help you every step of the way, from a request for a proposal to the follow-up and payment process. 

The magic of web-based proposals

All of our documents are web-based, meaning they get sent as links to landing pages. This allows us to track the readers with proposal analytics. 

We know exactly when they opened your documents, how much time they spent on each of the sections, when they digitally signed and paid and whether they forwarded your proposal to anyone. 

This type of data is priceless in the follow-up process since it tells you everything you need to know. 

If your clients haven’t even opened your proposal and you start bombarding them with emails and messages, they might get turned off by your offer. 

Dealing with unpaid invoices and sending payment reminders is never fun. Sometimes it can drag out and cost you more time and effort than money.

That’s why it’s important to have a bulletproof strategy for reminding someone to pay you without feeling awkward about it. 

Once you know how to shape your approach, it’s important to have an open line of communication with your team members. Explain the situation to them and make sure they understand how it will impact their day-to-day work. 

As soon as everyone is on the same page, you can get back to work without sacrificing your team’s productivity levels. 

Otherwise, you will constantly be in the situation of asking someone to pay and dealing with a new overdue invoice.

Key takeaways

If the question How to remind someone to pay you? is often on your mind, you can follow our easy guide. It will also help you be proactive about these types of situations and make sure that you don't end up in situations where you have to remind someone to pay.

If you want to automate your client’s payments and charge them upfront, sign up for Better Proposals. We can help you transform your sales process by selling more products and services faster. 

Our sales documents will help you avoid ever having to ask yourself how to remind someone to pay you.