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Chasing small overdue payments is a nightmare. It keeps CFOs and their teams up at night with sheer exhaustion and frustration.

At best it’s something that saps your time and your soul. At worst it will have you questioning life and reality.

It’s something so many of us have gone through. And it’s an end-to-end process that always follows the same pattern.

Does this sound familiar to you?

The Polite Reminder

Okay, so you‘ve just noticed that a client has missed a payment. You think “Hmm, that’s odd and send them a gentle nudge- a polite reminder sent. But first you agonize over the wording – DON’T BE RUDE!

There might even be a few smiley faces in there (you know who you are) and not too many exclamation marks. Anything to remind them “We’re friendly! We’re not mad! You can pay in this very easy way and let’s put it behind us.”

And then…tumbleweeds in the inbox…

Chasing Small Overdue Payments

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The Voicemail Diplomat

So then you move on to the next stage: phone calls. Your optimistic fingers might dial, excited, anticipating something. Anything.

Nothing except endless rings. On hold to the same two songs everyone plays when you’re on hold, and then, just the voicemail.

So you leave messages so diplomatic you wonder how on earth no one ever contacted you to be an ambassador.

Yes, it’s urgent but we’re here to listen

We understand what you might be going through

We’re looking forward to sorting this out for everyone

And the calls are unreturned.

Your eye starts to twitch. You might pop an ibuprofen. Maybe two.

The Passive-Aggressive (but oh so Creative) Escalation

Desperate times call for desperate measures. Trying to get their attention in any way possible. Eye-catching payment reminders. Meme-inspired emails. Poetic verses about the beauty of prompt payments. And when it gets bad, the LinkedIn post about paying on time.

It’s all creative ways to get the client to definitely, absolutely, fully know that they have our attention. All you want is to not have that invoice sitting on your desk or blinking on your screen, mocking you. Mocking you most cruelly.

Which is a fun pressure to feel when you’re talking to stakeholders about revenue in.

Note: this is where the sleepless nights really kick in.

The Great Detective

Because you obviously have nothing better to you, it’s time to channel your inner Angela Lansbury. Or Poirot. Or Benoit Blanc. (Whatever floats your boat.)

And with your double espresso because you’re tired, you try to find them. LinkedIn. Facebook. Twitter. Insta. TikTok. Looking for something that gives the slightest bit of hope that they’re 1) alive 2) still trading 3) have money to pay their debts.

You probably know where your client likes to get their coffee, and what their favorite band is, but unless you find some magical sentence like “just landed a huge account”, you’re probably feeling a lot more nervous.

The Emotional Roller Coaster

Days turn into weeks. Weeks into months. You’ve been sending them more messages than your best friend. You don’t even remember the last time you didn’t think of them.

The emotions are all over the place. Hope. Despair. Cruel optimism. Frustration. More excuses. More “It’s getting paid today. It’s first on the list” as you pop ulcer medication and eyeroll yourself into a coma.

And you can’t believe how much time and mental space this overdue payment has cost.

Then the big philosophical questions start – What is life? This can’t be it, right? What has happened to me?! Will I never be able to close out this invoice spreadsheet?!?  

Epilogue: The Triumph (Or So We Hope)

But then, 2 months late, 5 months, 7 months late, it happens! It’s paid. Not with a bang, but a whimper. It really happened! You won!

You no longer have to sleep under your desk. You can emotionally let the chase go. You’re packing up to finally go home, and then…

You realize another client’s payment is late.

Give me strength.

It’s a truly awful experience. It takes its toll on your work life and your bottom line.

Chasing Small Overdue Payments

You’ve probably already tried things to tackle this problem (besides changing your name and leaving the country and business altogether). But just in case you missed one, here are some things you can do to cut down on the frequency of chasing small overdue payments:

  • Set up clear payment terms from the beginning
  • Follow it up more regularly (ie before the payment is late)
  • Change your approach from aggressive or confrontational to collaborative from the start
  • Stop using the wrong way to communicate (ie email chasing vs. a phone call)
  • Offer flexible payment options using the client’s preferred method of payment
  • Use automation so that much more of the process is taken care for you.

Whatever you decide to do, just know that you’re not alone. Most finance people know all about this, the worst end-to-end process.

Hang in there- that payment’s coming. Eventually.

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