Send a short list of what is outstanding to each customer, name a date, and make paying easy. Most late invoices are unpaid because nobody was reminded.

Why this week works

Chasing payment in December feels like poor timing and is usually the opposite.

The person who approves your invoice is also trying to finish things before they close, and a clear reminder helps them do that.

Many businesses want costs settled within the financial year, which gives them a reason to pay now rather than in January.

And once everybody closes, an unpaid invoice waits until the second week of January before anybody looks at it.

Most late payment is not refusal

Which changes the tone of the whole exercise.

The common causes are an invoice that never reached the right person, one sitting in an approval queue, one missing a reference the customer's system requires, and one simply forgotten.

None of those is resolved by waiting, and all are resolved by a short message.

Which means chasing is usually helping rather than pressing, and it should read that way.

Assume an oversight until you have evidence otherwise, because that is what it almost always is.

What to send

The last item does more than the rest combined, because it converts a demand into an offer of help and surfaces the actual blocker, which is frequently a purchase order number or a wrong address.

Attach the invoices again

Since the most common blocker is that nobody can find it.

Do not ask them to look it up, and do not refer to an invoice sent in October as though they have it open.

Attach copies to the reminder, so the person can act without going anywhere.

Include the payment details in the body of the message as well as on the invoice, since somebody paying from a phone will not open an attachment to find them.

Every step you remove increases the chance it is paid this week rather than added to a list.

A worked example

A business had eleven unpaid invoices in mid-December, several from October.

They sent one short message per customer with a list, the attachments, the total, and a question about whether anything was missing.

Four were paid within three days.

Three replied that they needed a purchase order number on the invoice, which had never been mentioned and had been holding them since October.

Two asked for a January date, which was agreed and honoured.

Two did not reply, which was useful information about those customers.

Ask for a date rather than payment

A small change in wording that produces more replies.

When can I expect this is easier to answer than please pay, because it asks for information rather than money.

Somebody who cannot pay this week can still give you a date, and a date is considerably more useful than silence for your own planning.

It also creates a commitment you can refer back to without any awkwardness, since you are following up on their own answer.

Where a customer names January, accept it, note it, and follow up on that date rather than before.

Ring the ones that matter

Since email is easy to defer and a call is not.

For the two or three largest, a short friendly call finds out in a minute what a fortnight of email will not.

Ask for the person who processes payments rather than your usual contact, since those are frequently different people and your contact may not know the status.

Be pleasant and specific: which invoice, what date, is anything needed.

Most such calls end with an explanation and a date, and a proportion end with it being paid that afternoon.

That is an uncomfortable twenty minutes with a better return than anything else this week.

Fix what caused it

While the reasons are in front of you.

Where several customers needed a reference or a purchase order number, add that field to your invoice template.

Where invoices went to the wrong person, record the correct billing contact for each customer now.

Where terms were unclear, state them plainly on the invoice: what the terms are and what happens after them.

And where nothing was ever chased until December, set a routine: a reminder at seven days past due and another at twenty-one.

That routine is what prevents next December being the same exercise.

Deal with the genuinely old ones separately

Since an invoice from six months ago is a different situation.

By that point it is either disputed, forgotten by both sides, or from a customer in difficulty, and a routine reminder will not resolve any of those.

Ring rather than email, and ask directly whether there is a problem with the work or with paying, since one of those is usually the answer.

Where it is a dispute nobody raised, that is worth knowing even if it costs you the invoice, because the same misunderstanding is probably in your other jobs.

And decide what you will do if it is not paid, before the conversation rather than during it, since a threat you have not thought through is worse than none.

The counter-case

Timing is a judgement.

Some customers genuinely cannot pay until January and chasing hard achieves nothing except damage to a relationship worth more than the delay.

A message that reads as pressure at Christmas is remembered, which is why the wording matters more than usual.

And for a business with two outstanding invoices, this is two messages rather than a campaign.

Send the list, attach the copies, ask what is missing, and ring the largest two.

This week

  1. List everything outstanding.
  2. Send one message per customer.
  3. Attach the invoices again.
  4. Put payment details in the message.
  5. Ask what is missing.
  6. Ring the largest two.
  7. Set reminders for seven and twenty-one days.

Step five is the one that finds the real blocker, since a purchase order number nobody mentioned can hold an invoice for three months without anybody raising it.

Taking money before the work is covered in holding a deposit on work you cannot schedule.


Frequently asked questions

Is December the wrong time to chase?

Usually the opposite. The person approving your invoice is trying to finish things before closing, and many businesses want costs settled within the financial year.

Why are invoices unpaid?

Rarely refusal. Usually the invoice never reached the right person, is in an approval queue, is missing a reference their system requires, or was forgotten.

What should the message contain?

A list of what is outstanding with numbers and dates, the total, how to pay, a date you would like it by, and a question about whether anything is missing.

Why attach the invoices again?

Because the most common blocker is that nobody can find it. Put payment details in the message body too, since somebody paying from a phone will not open an attachment.

What wording works better?

Asking when you can expect it rather than asking for payment. It requests information rather than money, and a date is more useful than silence for your planning.

What should I fix afterwards?

Whatever the replies revealed: a missing reference field on your template, the correct billing contact per customer, and a reminder routine at seven and twenty-one days.

West Coast Media Solutions Inc. provides web design, web development, hosting, digital marketing, and business consulting to organisations across Canada, drawing on more than twenty-five years in the field.

Invoices outstanding from October?

Send a list with the copies attached and ask what is missing. A purchase order number nobody mentioned holds invoices for months.

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