10 ways to eliminate awkward conversations and get paid

Even in the accounting business, talking about money can feel uncomfortable. And when it comes to getting paid by your customers, it can also be a bit of a balancing act.

After all, you need to get paid, and preferably sooner rather than later in today’s climate. Otherwise, your cash flow will be squeezed, making it harder to plan ahead, make decisions, or spend on new purchases and investments.

At the same time, you don’t want to annoy customers by repeatedly asking for what you’re owed; you’ve likely spent time and energy building a great relationship that will hopefully bring more business.

But you’re not providing products or services for free. You must have the payment conversation at some point. Fortunately, there are ways you can make the whole thing less of a big deal.

In this article, we give ten tips that will help you eliminate awkwardness from these conversations, preserve relationships with your customers, and most importantly, get the money you’re owed.

1. Show understanding
2. Communicate payment terms early
3. Talk about more than money – Ask for service feedback
4. Frame as questions
5. Be responsive throughout the project
6. Personalize invoices
7. Automate where possible – recurring invoices, automated reminders.
8. Share what other customers do
9. Share how your business is affected
10. Thank customers no matter what

Show understanding

Having empathy for your customers is essential in making conversations smoother. This starts with trying to understand the motivations and pressures around delaying payment.

You might consider:

Are they dictated by strict processes?

Are they so busy that paying you isn’t their top priority?

Are they just procrastinating?

Figuring out what might be stalling them will help you take a nuanced approach to talking about payment that will resonate and drive them to settle an invoice.

Whatever the case, you’ll need to remove as many obstacles as you can, so that settling your invoice is easy to do. That could be simplifying the payment process, adapting to the customer’s needs, or giving them polite but regular reminders.

In other words, be compassionate to their situation and try to support them but stay persistent.

Communicate payment terms early

Making sure that you and your client are on the same page in terms of payment needs to happen early in the process. This is a preventative measure that reduces awkwardness further down the line. There are several ways to do this depending on how your business works, but the most essential element here is clarity.

There should be no confusion about when you expect to be paid and what the options are for making the payment. It’s also better to confirm this in writing, so that both parties have something to refer back to if they need it.

Much like tip four reveals, talking about these terms can be part of a wider conversation.

Talk about more than money

When you need to talk about payment, it’s good to raise your points within wider conversations. That’s because booking a meeting specifically to discuss payment and nothing else puts all the focus on what’s sometimes a sensitive topic.

Instead, you could arrange a service feedback session, and discuss payment at whatever point in the conversation that feels natural.

This works great, because the customer will know you value their opinion and want them to be happy with what you’ve delivered. You can also share how you felt the project went and offer to tie up any loose ends, which reinforces the value you are providing.

By broadening the conversation, you show that you care about more than just money, which puts your client in a more receptive frame of mind for when the topic does drift in that direction. You’ll also learn more about what your customers need, helping you to tailor their experience and inform future conversations.

Frame payment terms as questions

Another tactic when discussing payment terms is to position them as questions whenever possible. If you’re flexible when it comes to how you’re paid, whether you accept payment up front, or how to schedule recurring payments, framing these as questions can be very accommodating to customers.

Asking “how would you like to pay?”, “do you prefer to pay up front?”, or “would you like to be invoiced monthly or quarterly?” takes away some of the pain of payment.

On the other hand, asking the client to agree to your preferred terms might introduce some friction if any go against their usual methods. This will sometimes be unavoidable, of course.

Be responsive during the project

A client that has experienced fantastic, attentive service throughout a project is going to be much more motivated to pay you quickly. This means getting back to them promptly when they contact you, completing any agreed actions, and doing whatever you can to ensure the project stays on schedule.

Of course, these are the kind of things you’ll likely be doing anyway, but it’s worth thinking about them with future conversations around payment in mind. If you’ve been slow to reply to emails, forgotten to do things you’ve agreed to, or failed to meet deadlines, chasing payments after delivery will only be more awkward.

Make paying invoices effortless

The easier you can make the actual act of settling an invoice, the more likely the customer will be to get it done. This where technology comes in. If you can, you should aim to use an invoicing solution that allows your customers to pay however, whenever, and from wherever they want.

There are a few invoicing capabilities that you’ll find particularly useful when it comes to getting paid quicker; from personalization to including a ‘Pay now’ button directly on the invoice.

Features like these make conversations less awkward by cutting out any excuses around the payment process itself. By making it faster, easier, and more flexible to pay, you’re anticipating and removing potential objections.

Automate where possible

A great way to skip past some discomfort (especially in the early stages), is to take advantage of automation. Many accounting software solutions offer features that remove some of the need to chat to customers about payments.

Of course, you don’t want to lose the human touch entirely, but being able to set recurring invoices and automated reminders can be incredibly effective. As well as saving you time by removing the need to do these tasks manually, automated notifications improve accuracy and consistency too.

Regular customers will get to know how often these types of messages come in, helping them to better understand your expectations and keep your business front of mind.

Share what other customers do

Behaving in line with others is a great human motivator. For particularly slow-paying customers, subtly highlighting that they are behind the average in settling your invoice can trigger them to do so quicker.

You can drop this into conversation at any point during the relationship. Even before work has started, you could mention it when discussing payment terms, using language such as “we stick to the usual 30 days after invoicing, but most of our customers get it out the way within a week” (or whatever time is true for your business).

Another approach is to add a similar line as a note on personalized invoices, or within emails. Just remember to frame it almost like you’re making them aware, rather than setting a demand.

Be open about your business

If you’ve been chasing long after an invoice is due, you might feel that you need to change tone.

Of course, you never want to be impolite, but if friendly reminders haven’t worked so far, you need to adjust your language to reflect the seriousness of the situation.

Instead of sternness, another approach is to appeal to the client’s better nature. You may be showing a bit of vulnerability but try explaining how waiting for their payment is impacting your cash flow and that timing is crucial for a small business like yours.

This can be quite effective if your client is a larger organization that’s simply unaware of how significant that impact might be.

Thank customers, no matter what

There are many reasons your client may have delayed paying you. Though sometimes it’s a simple case of procrastination, it could also be because they are facing cash flow issues of their own. You won’t always know their motivation, but once they’ve paid you should always thank them.

Even if the lateness has caused you some difficulty, showing appreciation is essential for protecting that relationship going forward.

If you don’t make the effort to send an email or thank you note, they’re going to be less motivated to pay you quickly next time, which may make for future awkward conversations.

Final thoughts

With tough economic conditions on the horizon, finding the balance between making sure you’re paid and not hounding customers will be extremely important. Following these tips to adjust your language, make use of technology, and reduce the pain of paying, will help you get there.

Just remember that your customers are facing those same conditions, so being understanding and supportive will go a long way in protecting the relationships you’ve worked hard to build.

Editor’s note: This article was first published in November 2022 and has been updated for relevance.