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Overdue Invoices? Simple Tips To Ensure Your Clients Pay On Time, Every Time. No More Overdue Invoices

by Sheldon Nesdale on 5 November 2013

in Marketing

  • Did you know that poor cashflow is the #1 killer of small businesses world-wide?
  • Do you have clients with overdue invoices right now?
  • Do you grit your teeth when you check your bank account on the 20th of the month and find the deposits you were expecting, missing?
  • Are your customers/clients slow to pay?
  • Are your invoices due on the 20th of the month but sometimes they don’t get paid until much later? Sometimes 60 days or 90 days?

Well you’re in luck, because today I’m going to tell you how I get the following results:

  • 89.6% of my clients pay on time (within 7 days)
  • 9.4% of my clients pay within 7 days past due
  • 1% don’t pay at all, but only because they go bankrupt (no fault of mine, I assure you)
  • I’ve never needed to use a collection agency

Here’s how you can get results like that:

4 Ways to Ensure Your Customers/Clients Pay On Time, Every Time

1. Change your terms to 7 days

Do it.

Right now.

Send out an email to warn everyone that it starts this week.

When your terms are 7 days your clients will file your invoices right under their accounts-payable-clerks nose for immediate attention.

Invoices that are due 20th of the month are so easy to ignore, or postpone, or forget about, or get lost.

“But my client’s accounting system can’t handle paying within 7 days!


Ask nicely for an exception.

I’ve been paid within 7 days from Government Departments, City Councils and District Health Boards. Their policy is to pay 20th of the following month but they all made an exception for me because I asked for it.

2. Email your invoices instead of posting them

Ask for the accounts-payable-clerks email address and email them directly (and cc your contact at the company too).

No more posting. This slows things down far too much. And with 7 day terms, 3 of those days are used up in printing/delivery.

Don’t know how to convert your invoices to PDF? You don’t need Adobe Acrobat Professional (NZ$600!), just download 1 of hundreds of free/cheap PDF writers (they install as “virtual printers”).

3. Stop sending statements with OVERDUE stamps on them

Receiving a statement with a big red overdue stamps on it is like slapping your client in the face with a wet fish.

Acutally, it’s like slapping the accounts-payable-clerk in the face with a wet fish because your contact at the company will probably not even see this document.

Why would you treat the person who is going to pay you like this?

It is a deep insult. It is shouting out “You are crap at your job! Paying invoices is easy but somehow you screwed it up! Wow, you really suck!”

If you sent me a statement with a big red, angry overdue stamp on it, I would purposely not pay you just to piss you off.

4. Within a few days of the invoice being overdue, email a reminder

Send the following reminder to the accounts-payable-clerk and copy in your contact at the company too.

With these exact words: “Hi Bob, I just noticed invoice #1234 is a few days overdue. Would you like an extension?”.

That’s it.


To the point.

No waffle.

Notice the first part “I just noticed”? This lets them know that you know it’s overdue. It lets them know you are watching. Now they know that you know.

And notice how it ends with an open ended question?

I could have said “Let me know if you need an extension.” But this isn’t as powerful, because it isn’t a question. It’s weak. Don’t use it.

The magic of asking a yes/no question like “Would you like an extension?” is that people instantly form a response in their heads once they’ve read it.

There are two possible answers. Yes, and No.

Most of the time they are too proud to email you back and say “yes, could we have until the end of the month please?” (although some do, and that’s perfect fine, now you have a new due date to work with).

So they will think “no” in their head. “No, I don’t need an extension, I’m going to pay this today to show them how in control I am of my finances!”. You might not get an email response from these people but the payment will turn up in your bank account the next day.

Why this method works so well

You must stick to this schedule because this is how you train your clients. It lets them know what your expectations of them are, and they quickly learn what to expect from you next time.

If you ease up, that’s when it slips away and you’ll spend more time chasing overdue invoices and less time serving clients.

What if you still don’t get paid?

Wait another 7 days and send this email (and attach the invoice): “Hi Bob, could you check on invoice #1234 for me please? It is now a few weeks overdue. Would you like a further extension?”

What if you still don’t get paid?

Wait another 7 days and send this email (and attach the invoice): “Hi Bob, Invoice #1234 is now 4 weeks overdue. May I have payment today please or would you like a further extension?”

What if you still don’t get paid?

Wait 30 days and then email them every day with a variation like this:

  • “Hi Bob, just checking on invoice #1234, may I have payment today please, or would you like a further extension?”
  • “Hi Bob, could you have another look at invoice #1234 please. Could you arrange payment today please, or would you like a further extension?”
  • “Hi Bob, I just wanted to check on your payment for invoice #1234. Could you make that payment today please, or would you like a further extension?”
  • “Hi Bob, I was hoping to hear from you by now. May I have payment on invoice #1234 today please, or would you like a further extension?”

The key is to not get angry. Keep your tone respectful and calm. Don’t acknowledge that you are being ignored.

“Why not just pick up the phone and call them?”

Because emailing saves face. It’s embarrassing to make a call to ask someone to pay, and its even more embarrassing to receive one. Email creates a comfort zone.

“What if they do ask for an extension?”

Fantastic! That is a great outcome. It’s not as good as getting paid, but it is pretty close.

Remember, they have chosen the new due date, you didn’t choose it for them. So reset your reminders and as soon as that new due date lapses without payment, repeat the process outlined above.

“This seems like a lot of work, is it really worth it?”

Once you have set expectations using the suggestions above, very few clients will progress to the daily harassment stage.

“How about I just use a collection agency instead?”

No. It’s your problem. It’s your fault for not training your clients properly. You deal with it.

What do you think about this advice?

What tips do you have for dealing with late invoices? Tell your story in the comments below.

{ 83 comments… read them below or add one }

1 Lucy Smith June 3, 2011 at 12:32 pm

β€œThis seems like a lot of work, is it really worth it?” To which I’d answer: is it worth doing work you don’t get paid for?

These are some good suggestions – normally I give them a week after the invoice is due and follow up with a statement. I like the idea of the open-ended question.

I’ve never had a bad debt, just one client I had to chase for a couple of months for the invoice (it was less than $300). The work never got used either!


2 Sheldon Nesdale June 3, 2011 at 12:42 pm

Excellent point Lucy, thanks for that πŸ™‚


3 Good Websites | Erwin June 3, 2011 at 12:54 pm

Great tips Sheldon!

Not 100% sure about only emailing the invoice. We’re sending an email and a printed version of the invoice to prevent ‘huh? didn’t receive any email…’ (hehe…)



4 Sheldon Nesdale June 3, 2011 at 12:55 pm

Thanks Erwin!


5 Gareth Robins (Auckland Wedding Photographer) June 3, 2011 at 2:15 pm

Great post and I like the tone of the emails, very non-confrontational. That’s important to maintain a good relationship with people afterwards.


6 Sheldon Nesdale June 3, 2011 at 2:18 pm

Very true, thanks G-Dog


7 Sheldon Lendrum June 7, 2011 at 10:25 pm

Great tips Sheldon, I have now removed the OVERDUE flag from all my invoices, and put a nice message in the email that says “Your payment is a little late, please give me a call or make payment as soon as you can !”


8 Sheldon Nesdale June 7, 2011 at 10:34 pm

Cool, thanks for that report Mr Lendrum


9 Chris Bell August 1, 2011 at 12:39 pm

This is all good advice, Sheldon. Sadly though, there are too many companies that simply won’t make an exception to their accounting policies. This applies in particular to the largest, which generally have to raise a purchase order before you submit your invoice. It would be relatively simple for them to issue a PO at the time of commissioning the work from you, especially when these are what amount to ‘petty cash’ payments for them, so that the money is available for payment on acceptance of the work. Sadly, though, they won’t raise the PO until you invoice (most likely to protect their own delicate cash flow) and you’re left with no alternative but to drop them as clients. In the days when there was more than enough work I could afford to sit out the delays; nowadays I can’t risk blocking in time to do work for them and potentially missing out on other work if they’re not going to pay until the 20th of the following month. This is one of the (many) ironies of freelancing.


10 Sheldon Nesdale August 1, 2011 at 12:43 pm

Thanks for your thoughts on this Chris


11 Matt @ Kurb August 26, 2011 at 4:58 pm

Just came from twitter, I need to sort this out. It’s not as if big companies won’t pay, but the extent to which invoices go missing and get overlooked I find is ridiculous. And you can’t get haughty with your contact about it, it’s not their dept.! The issue really is as chris puts it, can you afford to alienate big clients because of your terms?

This is business in NZ. New Zealanders are going to stick with suppliers and providers that they personally like and appreciate. It’s such a fine line, and with the media and friends full of doom and gloom it seems sacrilegious to turn away business because you won’t wait a month or 2 to get your money.


12 Sheldon Nesdale February 29, 2012 at 3:55 pm

Sorry Matt, I read this message of yours when you posted but didn’t write a reply at the time.

I say: if a big client can’t pay you on time, find another one that will. The worst situation you can be in is to have just a couple of really big clients that are slow to pay you. It will kill your business. Give them a chance to follow your payment rules, and if they can’t do it, fire them.


13 Pippa Wheeldon August 1, 2012 at 10:20 pm

This is something we’re experiencing far too often now and can seriously affect cashflow when you have 20+ clients all settling invoices a month or two later than they should be.

We’re doing pretty much all of the above already – to little success. I’m thinking we may reduce the payment terms to 7 days however (rather than 14) and send an announcement out to all clients to explain why. Maybe this could make a difference.


14 Sheldon Nesdale August 2, 2012 at 4:09 pm

Yes, 7 is better. It prompts faster action “ooo, I better get this to accounts because it’s due soon”. 14 days is very forgettable.


15 Leanne Briggs August 7, 2012 at 5:12 pm

So if you have terms of trade and email/phone customers checking they have their invoices and they haven’t paid and haven’t paid, what time frame do you have for sending a letter threatening legal action. We do use that tool as it is reasonably effective too for the very slow payers – individuals, rather than companies.


16 Sheldon Nesdale August 8, 2012 at 12:42 pm

Never ever ever threaten legal action. Everybody loses in that scenario. You have 2 choices:

1) Give up and write off the debt (sometimes its best to just get on with life)
2) Email them every day as per my instructions above (repeated here for your convenience):

Email them every day with a variation like this:

β€œHi Bob, just checking on invoice #1234, may I have payment today please?”
β€œHi Bob, could you have another look at invoice #1234 please. Could you arrange payment today please?”
β€œHi Bob, I just wanted to check on your payment for invoice #1234. Could you make that payment today please?”
β€œHi Bob, I was hoping to hear from you by now. May I have payment on invoice #1234 today please?”
The key is to not get angry. Keep your tone respectful and calm. Don’t acknowledge that you are being ignored.

β€œWhy not just pick up the phone and call them?”

Because emailing saves face. It’s embarrassing to make a call to ask someone to pay, and its even more embarrassing to receive one. Email creates a comfort zone.

You’ve heard the old saying “the squeaky wheel gets the grease”? Well, be the squeakiest damn wheel that guy has ever heard in his life.

If you get to the point where you can’t be bothered emailing every day, then move to option 1 and give up. Don’t be ashamed of that choice. It can actually feel just as good as getting paid because you’ll feel the weight come off your shoulders.


17 Robert May 8, 2014 at 4:35 pm

Sorry, but I do not agree about never threatening legal action, you say to just give up and write off the debt? If they sent you a P.O. and took delivery of the product then they should pay for it! this no paying action happens more often then you think and really hurts the economy, thousands if not millions of dollars in taxable profits are lost each year I an sure because of this practice! alot of these companies simply order product from their suppliers knowing that in a few momths they are going to go out of business so they just do not pay their bills! why let them get away with this?


18 Sheldon Nesdale May 8, 2014 at 10:32 pm

Hi Robert, thanks for your input on this. It’s simply the idea that you need to decide if the amount you are due outweighs the costs of court/lawyers, your preparation time and having that negative energy in your life, and the chance of them not paying in the end despite a court decision. All the best!


19 Dan May 29, 2014 at 6:40 pm

Sheldon, you article is possibly the best I’ve read on the subject and if your only dealing invoices related to a couple hundred dollars, a law suit would not be in order. With my type of work, invoices are in the thousands. Even getting 66% is better than nothing.

20 Patrick November 21, 2012 at 1:53 pm


17 months after you wrote this, I used it for the first time with great success.

We never have a problem with bad debt but we have lots of slow payers and people who we need to call a number of times to get things resolved.

35 emails sent yesterday with “do you need an extension?” has resulted in 10 payments and 5 responses.

20 left…
Emails due to go next week.


21 Sheldon Nesdale November 21, 2012 at 2:22 pm

Wow, that’s fantastic! Thanks for letting me know, you’ve made my day πŸ™‚


22 scott November 21, 2012 at 2:29 pm

Sheldon you rock matey!


23 Sheldon November 21, 2012 at 3:31 pm

Hi Sheldon,

I also have shifted across to “Do you require an extension for this invoice?” and it has also changed this dramatically.

They appreciate being asked for it, and it tones down asking for money from the customers.

Much appreciated!



24 Sheldon Nesdale November 21, 2012 at 7:37 pm

Great! Thanks Sheldon!


25 Nina Mole January 24, 2013 at 3:53 pm

Hi Sheldon

I’m just on day 2 of having to email a client everyday! (and so far including the email that had the invoice attached I’ve had 5 emails ignored!)

How long do you email them everyday for before you would delete what you are advertising for them?

Thanks for your help, the rest of my clients are following up and paying after I have asked them if they require an extension. (There’s always one!)

Kind Regards


26 Sheldon Nesdale January 25, 2013 at 8:27 am

Hi Nina, great to hear about your successes so far. I want you to try 10 emails in a row. 1 every morning for 10 working days in a row. Vary the start of the email each day, and keep the tone light. No threats. You just want to be the squeakiest wheels he/she has ever heard. You’ll get the grease.

Let me know how that goes.


27 Nina Mole January 30, 2013 at 12:13 pm

Indeed it did work after Day 4 I got a reply and Day 6 payment!
Thanks so much for the tips as I have come away looking, professional and courteous and been paid!
Thanks again!
Kind Regards


28 Sheldon Nesdale January 30, 2013 at 4:23 pm

Oh wow, that’s great Nina!!


29 Jesse Archer March 1, 2013 at 5:49 am

This has made a major difference to the response our clients give us accounts team.

“Would you like an extension?” is the key question.

We’ve set a small message up as a template in Xero which can be customised on a per client basis.

I think clients appreciate human contact over our canned auto-followup email system.


30 Sheldon Nesdale March 1, 2013 at 5:51 am

Nice work! If customers detect a robot (some are better than others at this), then they are more comfortable ignoring the message. But if they suspect their is a human pushing the button and waiting there for a response, that gets more attention for the message.


31 Josie March 8, 2013 at 7:08 pm

How do i write an email about an overlooked invoice?


32 Sheldon Nesdale March 8, 2013 at 8:27 pm

Hi Josie. No changes to the recipe above. Assume they have seen it. Just go straight to step #4.


33 Jade Grobler May 20, 2013 at 11:12 pm

Hi , I like the suggestions here but what I have found has worked best for me is a 50% upfront deposit before eanywork is even started, if they have a deadline then the customer/client needs to hurry up on getting that or th elead time is moved forward, we do this because every1 has dead lines, and we cant meet all of them so the clients who are serious and willing to meet me half way we make a priority, and the 50% remaingin settlement fee is paid before the wotk is shipped out, this works so well you have no Idea, it sorted out almost all issue I hade with the clients forcing in rush jobs to the clients who “order” but never intend on actually paying us, this was a huge fight at first and yes i did lose a few very loyale customers but these are the customers that i normally had to wait 90 days to pay, I have just 1 more client on my books on the old system and he is now taking advantage, he is almost over 100k over due and I have been carrying his debt for almost 4 months, I need to get him on my new system but Im having trouble typing the email and putting it in a way with out scaring him away, i need him to pay up and settle his invoices and begin to pay me on a regular basis but Im scared I will scare him away, like the others, but this client I can not afford to lose but I also can not afford to carry his bad debt any longer, does any1 have any suggestions? please note that he has had a 20 year relationship with the company, i have only been in the company for 2 years now


34 Sheldon Nesdale May 21, 2013 at 6:48 am

That’s great advice Jade because that tests the clients ability to pay, excellent.

As for your client with the huge overdue balance you are only asking for what you already own so be bold. Give them a call, tell him your business runs on cashflow and that you can’t carry the debt, and ask them for a date when the debt will be cleared, and then put the above process into action.

All the best!


35 Tom January 10, 2014 at 10:43 pm

Sheldon, I can’t wait for my next client to not pay an invoice. So I get to practices on them


36 Sheldon Nesdale January 12, 2014 at 3:02 am

haha awesome, that’s the spirit Tom πŸ™‚


37 Jennifer S. January 28, 2014 at 4:38 pm

What would you suggest if after the work is completed at the time of payment the customer writes the check for only 2/3 the agreed amount? A customer was a landlord whose tenant didn’t want to live on premises where construction (our service) was taking place. We had in the contract that we would minimize disturbance, and we did, but they made that choice. They deducted rent from the landlord, who then passed on that loss to us. I see you don’t recommend a lawyer, what do you suggest? Do we just refer to the original invoice/contracted remainder? Do we acknowledge their difficulty but explain that it is not us who is in breach? Please advise ASAP.


38 Sheldon Nesdale January 28, 2014 at 8:43 pm

Hi Jennifer,

As you mentioned, your arrangement is with the landlord, not with their tenant, so the landlord still owes you 1/3. Follow the above process and be generous with the payment date for the remaining 1/3 as the landlord may be short on funds right now until they have another tenant.

I propose an email such as this:
“Thank you very much for paying 2/3rds of the invoice amount, we do appreciate it. We understand that you may be having cash flow problems at the moment so we have provided you with an extension for the remaining 1/3 until the xx of February, does that date suit you?”

If they miss that deadline, proceed with the rest of the steps in the method described above.

Involving a lawyer will not help. It adds lawyers fees for both you and them, and it’s likely they are short on funds anyway so diverting any funds they do have to a lawyer will not help you to get paid.

All the best!


39 Jacob Kuster February 27, 2014 at 6:43 pm

Interesting tips. I find with larger companies my experience has been completely reliant on the work ethic of the person commissioning me. For example; I finished two projects for the same company in the same week. Two invoices were sent out to two separate brand departments. This company has a two week cycle between processing invoices. Both clients had more then a week and a half to submit the invoices for processing. One does while the other does not. One payment is received a few days after the first cycle and another is not. Now the client that did not submit will have to wait for the next cycle two weeks later. Company policy. The worst is when my payment terms are ignored and once submitted they are held back for an additional 30 days by accounts payable. This all comes down to the person who submits the invoice. The only solution is as you mentions. Polite persistence with authority.

Its a hassle to deal with invoices but “firing” a very important client because of slow payments is not always option. Only other advice I could add to all the great tips given is to get to know the accounts payable department, learn the policies, learn the process , keep track of the schedule and make sure to follow up consistently because chances are you are not the only person waiting on payments.

The life of a freelancer is harsh. Most of your clients start by asking for urgent speedy production with deadlines that demand sleepless nights. You would expect the same on their end when it comes time to pay, yet that is usually not the case. This life style has taught me a lot about managing my budget and always anticipating these issues. Apart from keeping on your clients it would be best to start budgeting your finances months in advance. So you can manage financially in between the waiting process.


40 Sheldon Nesdale February 28, 2014 at 6:41 pm

Excellent Jacob, thanks very much for this πŸ™‚


41 Anonymous March 7, 2014 at 4:31 pm

“If you sent me a statement with a big red, angry overdue stamp on it, I would purposely not pay you just to piss you off.”

And then you’d lose my business, get a negative credit report, and likely be speaking with a collection agency and/or a lawyer. Good luck with that.

I don’t send overdue notices. I contact people directly by phone if I they don’t pay in a timely manner. This usually works very well, but in the rare case that it doesn’t, I stop doing business with them. I don’t have time to deal with incompetent people.


42 Sheldon Nesdale March 8, 2014 at 2:11 am



43 Nolan March 29, 2014 at 12:55 pm

Would it be considered bad form to fax a reminder to the company with the invoice attached?


44 Sheldon Nesdale March 30, 2014 at 1:58 am

Thanks for your questions Nolan. Yes, lots of problems with that. Having a fax machine in the first place is pretty lame. Secondly, if you know who to attention the fax too, you might as well email or call them instead.


45 martin engelbrecht April 15, 2014 at 10:31 am

Advice from South Africa, to get faster payment, I charge interest and an administration fee, a few years ago I waited 9 months for a large company to pay, the next time I had interest and an administration fee on the invoice, I just send out a reminder that the invoice from this date will be charged interest and an administration fee, now this large company phones me up to check I have received payment! I also don’t mind if they don’t pay as the interest and administration fee adds up … these are large invoices …


46 Sheldon Nesdale April 15, 2014 at 7:03 pm

oh wow, thanks for this Martin! I’m glad that techniques is working for you.


47 Tom May 16, 2014 at 6:25 pm

Cutting to the chase and peppering clients every day with polite requests for payment is working a treat!
I used to get a bit stroppy, that didn’t seem to work, but polite and emails every day seems to work after 7 days straight!
Plus the occasional ‘do you need a time extension to find the money?’ cheeky insult added in for good measure!


48 Sheldon Nesdale May 17, 2014 at 7:57 am

haha, that’s great Tom!


49 Belinda May 28, 2014 at 10:42 pm

We have a client who says they have paid on a certain date (7 days ago) but we still have not received payment. They have said it has left their account and is now trying to put it on us. How do you word a letter telling them that it is still outstanding when they are adamant it paid and is no longer their problem??


50 Sheldon Nesdale May 29, 2014 at 1:36 am

That sounds like a stalling tactic. All you need to do is wait a few days, check you account, and if the funds are not there, just email them back with “Hi there, could you double check your payment has gone through please? Your funds haven’t arrived yet”.


51 Digexart June 30, 2014 at 11:19 pm

I have a client that has buyers remorse. I have documented everything. They have made partial payment, but refuses to pay a balance owed for “out-of-scope” changes that were given out of the parameters of the original project.

I made the client aware by e-mailing a timesheet each week. At anytime the client could have raised concerns, but now the work is complete, the client wants to know why the charges are ‘excessive’. The client has the timesheet with all the hours and tasks. I have been courteous and professional, documenting everything. I have been waiting for payment, have sent emails, taking advice from lateinvoicetips (Thank-you). Now The client has become rude and dismissive. It is difficult to broach the subject.

What to do?


52 Sheldon Nesdale July 1, 2014 at 12:02 am

Ouch, that is certainly a difficult situation. It doesn’t sound like the “excessive” costs are a complete surprise to them so I think they are being slow to pay because of cash-flow issues. Therefore, keep up the daily emails asking for payment so that you are the squeaky wheel that gets the grease.


53 Digexart July 1, 2014 at 4:06 pm

I needed the work, and I ignored a warning sign when the client asked for a discount, or a reduction in price. Since I markup my prices for protection from these types of occasions, I marked it back down to my regular price no harm done right? I got the job. But at what cost? I am now playing the fools game with a client helping to sabotage my business.


54 Sheldon Nesdale July 1, 2014 at 8:53 pm

uggh. That must be very frustrating!


55 snkt July 16, 2014 at 9:03 pm

We have been doing this for years and most send cheques within 3 days or less. We do make exceptions for a few companies if asked. But if we do not receive payment in a timely fashion the next time the customer is told they have to pay before we leave or even 50% before the job. This works well and they even have to sign a contract. My biggest concern is the clients that think they can make their own invoice and just pay that amount just because they don’t like the cost. Still haven’t figured out how to deal with this.


56 Sheldon Nesdale July 17, 2014 at 6:49 am

Thanks for this snkt πŸ™‚


57 MoTeStr September 7, 2014 at 9:32 pm

I have a client who has ignored payment for several months now. I sent follow ups and the customer apologizes for the overdue invoice and says they’ll pay “ASAP”. The customer will always say that but never pay or give me a date. I set new payment deadlines and still same thing. I tried your method if sending daily emails. I received an email back saying he knows it’s overdue he doesn’t need to check the invoice again he’ll pay ASAP. Should I continue to email him everyday till I receive payment? Thanks!


58 Sheldon Nesdale September 8, 2014 at 8:59 am

Hell yes Motestr. Be that squeaky wheel! Get your grease!

There are 2 ways it could go:
1) He’ll actually pay
2) He’ll go quiet because he can’t pay right now

Either way, keep insisting on getting what is yours.


59 Allare October 4, 2014 at 6:29 pm

Hey Sheldon, thanks so much for these tips.
I followed them on my last project with great success. Right before I finished the project, the client started to avoid me and I thought it would be very hard to get paid. With your great tips, it worked like a charm!
So, many thanks for that.


60 Sheldon Nesdale October 4, 2014 at 8:34 pm

Oh wow, that’s great, thanks for letting me know Allare. Appreciate it πŸ™‚


61 Marcy October 30, 2014 at 5:29 pm

So we have a client that has not paid since April and we have tried this technique. He keeps asking for extensions which we give but its been something like 7 extensions and over 100 (in total) emails after each extension expires before a new extension is set up. I have a feeling he thinks he can extended indefinitely. I no longer want to give him the extension courtesy. What do you think I should do in this case. Its quite a large sum of money and we don’t want to lose this money


62 Sheldon Nesdale November 3, 2014 at 12:15 am

Ouch. Quite simply, he doesn’t have the money right now. So it’s a matter of being at the front of the queue if and when he does have money. It’s interesting he is still communicating because I would have expected him to go silent by now.

You have 3 choices:

  1. Continue the process and wait until he has money in his bank and can forfil his promise to you
  2. Get angry and threaten legal action (which will put you at the bottom of the queue to get paid)
  3. Write off the debt and get on with your life
  4. Choices #2 and #3 are so bad that I think you should stick with #1. What do you think?


63 Marcy November 7, 2014 at 6:11 pm

Well our last live contact with him has been over two month ago. Our emails and phone calls now go unanswered and we receive no read receipts from the emails we send now. As a pillar of society you would think he would want to clear this up.


64 Sheldon Nesdale November 9, 2014 at 8:58 pm

ah, I see.

In that case here’s what I want you to do: Email him every day for 10 days in a row. Maintain a pleasant and non-demanding tone in the emails (keep them short), and create a long, unique subject line that gets your whole message in there without him having to open the email, using the formula above.

Don’t miss a day. Don’t get angry or demanding. Be a sweet as pie.

By day 6 or 7 he’ll wonder if you will ever stop. You’ll be the squeakiest wheel he’s ever been in contact with. He’ll provide you with your grease.

Let me know how you go.


65 Designer November 13, 2014 at 4:29 pm

What I find most unsettling is people who are millionaires and skirt the issue of paying you a simple $700 bill. As someone who is not a millionaire in any way I would rather starve for 5 days then gain the reputation as someone who doesn’t have their finances in order and can’t pay such a small amount.
Also I have no problems sending such a person (one with obvious ability to pay) to collections just to mess up their credit. It then becomes unimportant to me about whether I ever see the money. It is about setting the bar for your business and teaching those types of people a valuable lesson. Not all small business owners are spineless. I did a job, you didn’t pay-now you will be the millionaire with bad credit for under $1000. Congrats! Sometimes we need to make an example out of clients so we can survive. Word gets around. Fast.


66 Sheldon Nesdale November 14, 2014 at 12:02 am

Interesting “Designer”. Thanks for your thoughts on this πŸ™‚


67 Sean Banks November 20, 2014 at 9:24 am

hey thats why billbooks has come up with an auto reminding feature… pretty cool.


68 Sheldon Nesdale November 24, 2014 at 12:07 am

ok, thanks Sean


69 Lena November 26, 2014 at 5:56 pm

I found this article a few months ago and started following your advice. Only today did I have to resort to sending “reminder #2”. Reminder #1 works like a charm. It’s amazing. I have been getting paid, and even trained some late payers. It’s the BEST advice for getting paid. Thank you so much for writing this article.


70 Sheldon Nesdale November 26, 2014 at 10:55 pm

Yay! Thanks for letting me know Lena, you made my day πŸ™‚


71 Chris McClimans February 17, 2015 at 12:15 am

I am a partner in a member run coop in the US.
We send out a discount inside our Statement Of Work (defines what we will do and for how much) that must be signed before work is started. We encourage prepayment be reducing the cost if payment is made before work begins.

Standard: 100% per hour
Discounted: 90% per hour pre-paid blocks of 40 hours

This catches the eye of any financial officers or folks who pay the bills and work quite well for us.


72 Lara March 24, 2015 at 12:15 am

Hi Sheldon,

Firstly, thank you for your website – so helpful and good of you to put this info out there.

I am a peripatetic music teacher who is very bad at chasing up unpaid invoices, and also rather lax at sending them out to begin with. Before you tell me how silly I am (and you’d be right!), I am currently in the process of changing my ways for future invoicing and late payment collection (and your tips are helping with this). However, I would like your advice on how to correct some mistakes that have already been made.

Firstly, I have some accounts that are about 2 YEARS overdue! How do you advise I follow these late payments up?

Also, I have been very slack in sending out invoices for the past year or so. How would you advise I invoice a student who I no longer teach for lessons provided a year ago? And how would you advise I invoice a current student for a whole year of lessons (instead of just one term)?

Many thanks in advance,


73 Sheldon Nesdale March 24, 2015 at 1:07 am

Hi Lara, thanks for your kind words.

Great questions!

1) 2 years overdue: Start with a phonecall and say “Hi there, I’ve just been tidying up my accounts and I noticed an invoice I issued to you a few years ago. I’m so sorry I haven’t gotten in touch with you before now! It’s for $xx. I’ll send you a copy in a moment, what email address shall I use for that? Ok thanks, what due date would you like me to put on the invoice?”

Notice how we are asking them to set the due date? That’s important. Last years due date is now irrelevant, and just saying “immediately” doesn’t help either. They need a new target to aim for.

2) 1 year with no invoice: Again, start with a phonecall to confirm contact details, and start the conversation a little differently: “Hi there, I’ve just been tidying up my accounts and I noticed that I didn’t invoice you for the lessons we did together last year…” And then use the other sentences above “I’m so sorry…”

3) Invoice for whole year: Use the same approach as written above. If you suspect the payment is too big for them to afford in a big chunk, ask the question “Would be easier for you if we split the payment into 3 chunks? What due dates shall we use for each chunk?”


74 steve May 19, 2015 at 6:17 pm

These tips are really helpful. I’ve been working for a major client for three years who have always paid on time. Now we’re picking up additional clients, Credit Control is a bit more involved. Your tips are helping me write a protocol so that we have a procedure to follow and no excuses for forgetting. Hopefully this will help us keep our 100% record.


75 raphy May 29, 2015 at 11:38 am

thanks man for the tips.


76 John F. April 27, 2016 at 5:39 am

Hi Sheldon,

I read your article titled “Overdue Invoices? Simple Tips….” and it is working great! I have collected most all outstanding debts and I feel much better with myself using the positive and open ended wording.

My question: I am a heath care provider in USA near San Francisco. I have collected almost all outstanding small debts (thank you!) but don’t have email addresses for one remaining bad debt following your recommended 3 collection attempts every 7 days ( I now request email addresses with new clients).

What do you recommend following the “30-day period of no response and then bombarding them everyday with an email” when I don’t have an email address? Thank you again for the positive suggestion.



77 Sheldon Nesdale April 27, 2016 at 9:31 pm

I get the impression you are trying to avoid an awkward phonecall? If so, you are not alone. πŸ™‚

The next thing I’d try would be the same sequence using SMS messages to their mobile device.

If that is not possible, let’s consider a phonecall. If you pick an odd time of the day/night like 7am or 8pm at night, you are more likely to get voicemail. With a voicemail you save yourself the stress and embarassement of a conversation, but you still get to say what you want to say.

More alternatives: an in-person visit, a tracked letter (signature required) delivered by courier (not regular mail).

I hope that helps πŸ™‚


78 Veronika Tondon August 25, 2016 at 7:04 am

I would suggest you Invoicera. It’s an online subbilling solution helps subscription billing, auto billing and auto reminder features. Besides that, you may also send estimates for s and expenses for approval to your clients. It is a feature rich solution with user friendly interface. (http://www.invoicera.com)


79 Sheldon Nesdale August 31, 2016 at 9:22 pm

Issuing invoices and reminders is the easy part Veronika. It’s collecting that’s hard.


80 Jean September 1, 2016 at 6:46 pm

I”m trying this today! It’s nice to ask for payment with such a positive approach. I’ll let you know how it goes. Thank you.


81 Sheldon Nesdale September 5, 2016 at 10:05 pm

Great Jean!


82 Sheldon Nesdale May 29, 2014 at 9:18 pm

Thanks for that Dan πŸ™‚


83 Dave Herron April 27, 2015 at 1:35 pm

Hi Sheldon,
Any tips for a masonry contractor? I repaired concrete curbs for a big apartment building on Cincinnati’s eastside. The apartment manager agreed to pay for the work on that day and has been hiding from me ever since. He said he was going to send the payment directly to my bank – he has the routing number and account and was supposed to deposit a penny to ensure that the payment goes to the correct account but he hasn’t even done that.


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