Late payments are, without a doubt, one of the most common headaches for small businesses. Often operating on lean budgets and quick working capital cycles, having access to cash is crucial. However, being too aggressive in your collections process can potentially lead to damaged client relationships.
Gateway Commercial Finance, an invoice factoring company, put together a two-day structured follow-up approach that is both professional and direct. By combining gentle reminders, clear communication, and professional documentation to your customers, you can improve your chances of getting paid on time without creating friction.
Day 1: Send the gentle confirmation email (within 24 hours)
In the event a payment due date comes and goes without a payment from a customer, your first step should be prompt but not aggressive. It’s always best to assume positive intent. Perhaps the client forgot about the invoice or maybe there was a technical glitch on their side. Sending out a short and polite email within 24 hours of the missed deadline will convey professionalism while also sending the message that you are monitoring invoices.
Day 2: Make direct contact and offer solutions (24-48 hours later)
If you haven’t heard back relatively soon after sending your first email, you shouldn’t wait weeks to escalate the issue. Should Day 2 pass with no response, a direct follow up the next day should be considered. Whether this is a phone call, follow-up email, or even a scheduled chat live or on video will depend on your relationship with the customer.
Direct contact makes it harder for an invoice to slip through the cracks, but it also offers you the chance to give the customer actionable solutions. The 2025 QuickBooks Small Business Late Payments Report, derived from a sample of over 1,700 small-business decision makers, found that businesses with outstanding invoices were owed $17,000 on average. Major corporations may not be impacted by such an amount, but for a small or new business it can be a meaningful sum.
Create and resend a clean invoice copy (if technical issues are suspected)
Beyond making direct contact, there is another step you can follow on the second day. Sometimes a late payment isn’t intentional. Emails can automatically go to spam, PDFs can fail to load, and things can get lost in digital translation. If you have reason to believe that a technical issue is to blame, re-sending the original invoice along with proof of receipt when it was originally sent on the second day isn’t a bad choice. In no circumstances should you amend the date of the original invoice.
Getting a clean copy over to your customer will not only reduce the number of excuses they can give you for not paying, but it will also show proof that they were already in receipt of the invoice and that you’re actively working with them to get the payment made.
Document everything and set the next action date (end of Day 2)
At the end of the additional 48 hours you gave your customer, you should now have a clear trail of documentation. The initial follow-up email you sent shows your outreach, your attempt to contact them directly shows a follow-up, and any re-sent invoice shows your effort to reduce error. At this point, it’s time to set an action date for your next escalation. This date shouldn’t be more than a week or two out, as you don’t want to let the issue fall through the cracks.
Copy-and-paste message templates
Considering that 38% of businesses fail due to exhausting their capital, according to Forbes data, there is no room for error. Below are some ready-to-use templates you can adapt for your own business:
Day 1 quick SMS option:
“Hi [Client Name], I just wanted to quickly reach out to confirm you received the invoice I re-sent on [insert date]. Please let me know if you need me to resend it and I will be more than happy to. Thank you!”
Day 2 phone follow-up or email content:
“Hi [Client Name], I tried giving you a call earlier today to quickly follow up on my note from yesterday about the invoice from [insert date]. I’ve gone ahead and attached a copy along with the original submission date here just in case the original was missed.. Let me know if there’s anything on your end that’s holding up processing. I’m more than happy to work with you on a solution if so.”
Professional email subject lines:
- Follow Up on Invoice [#] Sent on [Insert Date]
- Resending Invoice [#] – Please Confirm Receipt
- Friendly Reminder on Invoice [#] from [Insert Date]
Conclusion
Late payments most likely won’t ever disappear entirely, but that doesn’t mean you should let them slip through the cracks. By sending a gentle follow-up the day after a payment is due, reaching out directly if there’s no response, and creating a trail of documentation, you can cover your bases while increasing your odds of getting paid.
This story was produced by Gateway Commercial Finance and reviewed and distributed by Stacker.
