The following is from an answer I wrote to the same question posted on Quora. Also, the following answer is assuming that you don’t have something as leverage to get your payment (such as delivering the goods, etc.).
As others have mentioned, using a software tool that sends automated email reminders (like Harpoon & others) when an invoice is past-due is a great way to automate the initial steps of this process. I’ve freelanced for many years and it happens from time to time that a client just forgot about the invoice, had the intention of paying, whatever. My strategy for the automated emails is as follows:
- Payment is due: “Hey there! Just a friendly reminder that you invoice was due today. Let me know if there are any problems, and if the payment is already on the way, please disregard :)”
- Payment is 7 days late: “Hey there, just following up on that invoice that was due 7 days ago. Can you update me on when I can expect payment? Thanks!”
- Payment is 14 days late: “I’m starting to get concerned about the recent invoice that has gone unpaid. As you recall we agreed that my invoices should be paid [within x days, upon receipt], and I still haven’t received payment. I understand that these things happen, but I would like to know when I can expect your payment. Thanks.
- Payment is 21 days late: “It has been 21 days since your invoice was due and unfortunately I have not received payment. I would like to schedule a phone call to discuss this matter before taking any further collections action.
Hopefully you get the gist here, I like to start off friendly, because 9 times out of 10 they really did send the payment, or were just about to, or perhaps I forgot to mark the invoice as paid!
However, as time goes on, the tone gets more and more serious. There are people out there that will tell you over and over again that they are going to send payment. Many times they have believable excuses as to why they haven’t paid yet. Eventually you realize that they just aren’t paying and are taking advantage of you. These people are flaky and not the types that you want to do business with anyway.
At that time, you should send their invoice to collections.
Just remember, at all times, remain professional, don’t get personal even though it is indeed effecting you personally, and don’t make empty threats. Simply and calmly tell then that you’d like to work things out before sending them to collections, and if you can, great! If you can’t, then send them to collections and focus on serving and acquiring clients who do pay.