An invoice that sits unpaid for sixty days rarely got there because nobody sent a reminder. It got there because the reminders were three near-identical emails, sent whenever someone remembered, to an inbox that wasn't the one paying.
Nagging isn't frequency. Nagging is repetition with no new information. Six well-spaced messages that each move something forward read as competence. Two identical "just checking in" notes read as pestering. So build the cadence around one rule: every touch adds something the last one didn't.
The cadence
Days are counted from the due date, not from when you last got around to it.
Day −3 — the courtesy note. Short, no tone at all: invoice #1042 is due Friday, here's the link, tell me if anything looks wrong. This one isn't about payment. It's about surfacing paperwork problems — missing PO number, an approval that never happened, an invoice that never reached accounts payable — while there's still time to fix them. A large share of sixty-day waits start as a clerical error nobody caught in week one.
Day 1 — the receipt check. Nothing accusatory. "Invoice #1042 came due yesterday — can you confirm it's in the queue?" You're asking a question with an easy answer, and the answer tells you which problem you actually have. Silence here often means the invoice isn't in their system at all.
Day 7 — the specific ask. Now you ask for a date. Not "please remit at your earliest convenience" but "Can you tell me which pay run this is scheduled for?" A date is a commitment you can follow up against, and most AP teams will give you an honest one if you ask plainly.
Day 14 — the second recipient. Same facts, new person. Loop in the client contact who hired you — the one who wants the work to continue. AP processes what it's told to prioritize; your champion is the person who tells them. Keep the tone identical. The escalation is who is reading, not how loud you got.
Day 21 — the terms message. State the consequence once, flatly, and never repeat it. Late fee applies as of this date per the signed agreement; new work pauses at day 30. Repeating a stated consequence is how you teach people it isn't real. (Check your state's ceiling before you set a late-fee rate.)
Day 30 — the decision message. Give two doors, both easy to walk through: pay in full by a named date, or start a three-payment plan on Friday. People who have gone quiet are usually embarrassed, not hostile. A payment plan lets them answer you without admitting anything, and a client on a plan is a client who is paying.
After day 30 — one line every ten days. Dated, short, referencing the last unanswered question. You're keeping a live paper trail, not restarting the conversation each time.
Change exactly one thing per touch
Between any two messages, move one variable: the recipient, the ask, the channel, or the terms. That's what keeps a sequence from feeling like a machine. If nothing changed, don't send — wait until something does.
And stay in one email thread. A single thread with six dated messages is a record; six new threads is clutter that gets archived. When you eventually need to show someone the history, it's already assembled.
Small timing details that carry real weight
Send Tuesday through Thursday, early morning in the client's time zone — Monday is triage and Friday is a promise nobody keeps. Learn their pay-run schedule and land two days before it, not after. If they run payments on the 15th and 30th, a day-7 note that arrives on the 16th just waits two weeks. Ask once, early: "When are your pay runs?" Then aim at them.
One ask per message. Two questions in an email means you get an answer to the easier one.
Where cadences actually die
Not at the writing — at the sending. Day 7 falls during a launch week. Day 14 lands when you're at a client site. The sequence quietly becomes "whenever we remember," which is the state you were in before you wrote it down.
That's the part worth handing off. FetchDue runs the cadence from your own mailbox in your own voice, reads what comes back, drafts the payment-plan reply when a client asks to split it, and holds every message for your approval before it goes. The rhythm stays exact even in the weeks you have no attention to spare — and the relationship stays yours, because it's still your name on the message and still your call.
A good cadence isn't pressure applied on a timer. It's a series of clear, easy questions, sent to the right person, on a schedule you never have to hold in your head.