Friday, 4.15, payment run. The plasterer's invoice is in. His timesheet for week 42 is not. His public liability certificate expired on the 3rd and nobody noticed, because the copy you have is a photo of a photo on WhatsApp from last year.
You pay him anyway, because he did the work and he has a family, and you make a mental note to ask for the certificate. The mental note lasts until Monday.
The system keeps a file per subcontractor. Insurance certificate with its expiry date, the invoices received, the timesheets received, and which weeks are missing. When an invoice comes in and the timesheet for that week is not there, the sub gets a text asking for it. When a certificate is 30 days from expiry, the sub gets a message asking for the new one, and again at 7 days.
When a payment is about to go, you see a single line per sub. Green if everything is in, with a note of what is missing if it is not. Payment can still go through. You decide with the facts in front of you instead of finding out in an audit or after an accident.
The chasing is the bit nobody wants to do. It reads as nagging when a person does it and as admin when a system does it. We set it up so the messages come from your business and the files land in a folder per sub. What is the oldest insurance certificate you are relying on right now?