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Automate invoice chasing without souring a single relationship
Every outstanding invoice followed up on a courteous, escalating cadence you approve once - and a receivables picture you can read in one glance.
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Reminders, not collections
Get one distinction straight before any setup: this system sends reminders, not demands. The overwhelming majority of late invoices in a relationship business are late because the client is busy, the invoice slid below the fold, and nobody said anything - not because anyone decided not to pay. A courteous reminder at the right moment is not an imposition on the relationship. Silence followed by resentment is.
What makes chasing feel awkward by hand is that every reminder is a small emotional decision: is it too soon, will they mind, should I wait until after their event. A system makes the decision once, in calm blood, and then simply executes. The client experiences it as professionalism - which is exactly what it is. Your AskEleven Employee will run the cadence from your QuickBooks data, write every note as you would on your most gracious day, stop instantly when money or a reply arrives, and hand you a receivables picture you can read in one glance.
You stay in the loop at exactly two points: you approve the cadence and letters once, and you personally take over any account the cadence cannot resolve. Everything between those points stops being your job.
Before you start: decide four things
- Connect the books. QuickBooks (or Xero, or FreshBooks) connected through your AskEleven dashboard, so the system reads invoice status directly. This is non-negotiable: reminders driven by a spreadsheet go out against stale data, and one reminder for an invoice the client already paid costs more goodwill than a year of correct ones earns.
- Your cadence points. When does each note go? A sensible default for a services practice: a friendly note at 7 days past due, a firmer one at 21, a direct one at 40, and a handoff to you at 55. Adjust to your world - but pick numbers, because "when it feels right" is how invoices got to 90 days in the first place.
- Your client tiers. Not every client gets the same letter. A 20-year client with one late invoice gets more warmth than a new client with three. Two or three tiers is plenty: something like "longstanding," "standard," and "watch." Note any client who should never receive an automated nudge at all - there are usually one or two.
- The stop conditions. Payment received, payment plan agreed, any reply of any kind, or a dispute raised: each of these halts the cadence for that invoice immediately. Write them down; they go into the prompt verbatim.
Step 1: The cadence prompt
Set the machinery first, letters second:
You are taking over our receivables follow-up. Read our open and overdue invoices from QuickBooks every morning. Run this cadence per invoice: [7 days past due - friendly note; 21 days - firmer note; 40 days - direct note; 55 days - stop and hand the account to me with the full history]. Apply the client tiers I have listed - [longstanding / standard / watch] - and never contact anyone on the exempt list. Hard stop conditions, checked against QuickBooks before every single send: payment received, partial payment or plan agreed, any reply from the client, or any dispute - each of these halts the cadence for that invoice and routes the thread to me. One reminder covers all of a client's overdue invoices in a single note - never send anyone two reminders in one day, or reminders for the same invoice by two channels. All notes go from [[email protected] / my email], signed [SIGNATURE]. Nothing sends until I approve the letters and, for the first month, each day's batch.
What to expect: a playback of the rules and a first honest report of your aging - which is often the moment owners discover an invoice at day 84 that everyone assumed someone else was watching. The check-before-every-send rule is the one to verify hardest in testing: the mortal sin of automated chasing is reminding someone who paid yesterday.
Step 2: The letters
Three letters, escalating in directness, never in temperature:
Draft the three reminder notes, each in versions for our client tiers. Rules for all of them: short - under 90 words; plain subject lines ("Invoice 2041 - March furnishings"); state the amount, the invoice number, and the original due date without apology or accusation; attach or link the invoice so paying requires no archaeology; and offer the payment link if QuickBooks has one. The 7-day note assumes the invoice was simply missed, because it usually was ("I suspect this one slipped past - resending in case it is useful"). The 21-day note is warm but unambiguous that we are asking ("following up properly on invoice 2041, which is now three weeks past due - is anything holding it up on your end?"). The 40-day note is direct, respectful, and names the next step ("if there is a problem with this invoice I would genuinely rather know - otherwise we do need payment by the 15th"). Never: guilt, exclamation points, "friendly reminder" as a phrase, or any threat we would not act on. Show me all versions before anything is used.
What to expect: drafts you will edit lightly for voice, then approve as the standing set. The "is anything holding it up" question in the middle note earns its place - it is the line that surfaces the real reasons (a disputed line item, an invoice sent to a departed bookkeeper, a client quietly in trouble), and every one of those is better known at day 21 than day 60.
Step 3: The one-glance receivables picture
The chasing handles itself; this keeps you informed without opening QuickBooks:
Every Friday at 4pm, send me the receivables picture in one screen: total outstanding and how it moved this week; every invoice past due with client, amount, days overdue, cadence stage, and any reply received; anything that hit a stop condition and now waits on me; and anything approaching the 55-day handoff. One line of pattern at the bottom if you see one - a client who is newly slow, a month where everything is aging. No commentary beyond that.
What to expect: ninety seconds of Friday reading that replaces the low-grade year-round anxiety of not quite knowing who owes you what. The pattern line is worth watching over months: a longstanding client drifting from 5 days late to 35 is telling you something about their business before they tell you themselves.
A worked example: day 45 on the Hartley project
An interior design studio, mid-project with the Hartleys - longstanding clients, second home, lovely people, and invoice 2041 for the furnishings deposit is at day 45 with two nudges unanswered. This is precisely the invoice a studio principal never chases by hand: the relationship is warm, the project is ongoing, and every draft she starts feels either too soft to work or too hard to send. So historically, it simply ages.
The system, having no feelings about it, sent the 7-day and 21-day notes on schedule - warm, tier-adjusted, invoice attached. At day 40 the direct note goes out: "Anne - following up a last time on invoice 2041 for the furnishings deposit ($14,200, due March 3). If there is any problem with it I would honestly rather know. Otherwise we do need it settled by the 15th, as the workroom holds our production slot against it." The next morning, a reply: the invoice had gone to the address of a family assistant who left in February; nobody ever saw it. Paid by wire that afternoon, with an apology.
The reply hit a stop condition, so the thread routed to the principal, who sent one warm human line back - and updated the billing contact. Forty-five days of aging, resolved by three notes nobody at the studio had to write, and the relationship not only intact but slightly improved: the Hartleys now know the studio runs its business properly.
Quality tests, and the first month
- The stop test. Mark a test invoice paid in QuickBooks the day before its reminder is due, and confirm silence. Then reply to a test reminder and confirm the cadence halts and the thread reaches you. Run both before go-live; repeat after any change to the setup.
- The tone test. Read each letter aloud as if to your best client's face. Any sentence you could not say across a lunch table gets rewritten.
- The double-send test. Give a test client two overdue invoices and confirm one combined note arrives, not two.
- The recipient audit. Before the first live batch, have your Employee list every overdue invoice with the exact address the reminder will go to. Stale billing contacts are the most common first-week discovery - as the Hartleys demonstrate.
Run the first month with each day's batch held for one-tap approval. What you should observe: most invoices clear on the first or second note, the awkwardness you were bracing for never materializes, and the accounts that reach day 55 - there will be one or two - genuinely need you, which is the system working, not failing. After a clean month, release the daily approval and keep the Friday picture. The studio gets paid like a business that expects to be, which - it turns out - is most of what it takes.
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