How to ask for payment (when asking feels awkward)

Frankie Kemp

9 February 2020

Simon had his own engineering business. He was owed around £30,000 by clients.

This debt was now in its second year and he needed the cash to stop his business hitting the floor.

He had the whole situation under control, he said. They still meet him for drinks, he said. That means they’ll eventually pay him, he said. Meanwhile he was burning through around 40 credit cards before his business went bankrupt.

Whether you have your own business or you’re working within one, you may, at some point, need to chase the cash.

How do you do this assertively without sacrificing the relationship you have with your client?

They may have forgotten your invoice.  Cash flow issues might be preventing the prompt payment. However, your terms are what you agreed.

Some of the participants on my Effective Business Emails course raised this issue.  As a result, I’ve outlined a couple of iterations so you can see how we came up with the final request for payment.

We didn’t want to sound weak and apologetic. Neither did we want to get our guns out.

Draft One:

Reminding of the terms: Hi….. I hope you’re well. I just wondered whether payment is on the way for the attached invoice. I look forward to hearing from you today, if possible. All the best,,,,,

(weak – ‘just’ and ‘wondered / if possible’. You may as well pray for the money.??)


Draft Two:

Please let me know if it’s on the way and when I can expect it?

(wishy washy – don’t use. ‘On the way’ could mean they haven’t even passed the invoice to accounts yet.)


Draft Three:

Hi Carys, I hope you’re well. I’ve reattached the invoice for the xxxx work. Can you please confirm today that it will be paid by end of day Friday?

(specific deadlines stated as a question make this assertive but not domineering.)


Your Action:

  1. In your emails, set deadlines.
  2. Be very sparing with your use of the word ‘just’. If you’re using it to describe time such as in ‘I’ve just sent it’, that’s fine.  However, it’s often used as an unnecessary softener.
  3. In a strong request, be as thrifty with phrases like ‘I’m wondering if…’ It’s not direct enough. “I’m wondering if you’re free for a meeting, Sam”, for example, is better reworded as “Are you free for a meeting, Sam?” It sounds more confident.
Photo by Karolina Grabowska on

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