Quick Answer
Here’s what to send your bookkeeper monthly, and by when. Five things by the 5th: statements for any account not on a live bank feed, credit card and loan statements, receipts for larger or unusual purchases, payroll reports if payroll runs outside your accounting file, and answers to last month’s open questions. Three more are exception-based — new accounts, new loans, and contractor W-9s go over the day they happen. In exchange you should have closed books by the 15th: profit and loss, balance sheet, and a reconciliation report for every account.
You know the email. It arrives on the 3rd, it’s polite, and the subject line is something like “Quick items for the June close.”
You read the preview walking into a client call and think, I’ll do that tonight. Tonight becomes Thursday. Thursday becomes the following Tuesday. On the 14th your bookkeeper follows up, apologetically, and you feel vaguely guilty about a task that would have taken eleven minutes. Meanwhile your books sat there, not closed, for two extra weeks.
Most bookkeeping delays aren’t the bookkeeper’s fault. Yours can categorize eight hundred transactions in an afternoon and still not hand you a report, because one $4,200 deposit is sitting there and only you know what it was.
So let’s fix the handoff. This is the document I send my own clients during onboarding.
Why the 5th of the Month Matters More Than You Think
Pick a date and defend it. I use the 5th, for three reasons.
Your statements exist by then. They cycle at month end and post within the first few business days, so the 5th is the earliest date everything is actually available.
It leaves room to close by the 15th. If the packet lands on the 12th, your reports arrive around the 25th, describing a month that’s nearly two months gone. Data that old stops informing decisions and starts being a history lesson.
It keeps you inside the window to catch a bank error. Under the Uniform Commercial Code you have a duty to examine your statements promptly and report unauthorized signatures or alterations, and a same-wrongdoer rule can bar you from claiming later forgeries by the same person. How long you get depends on where you are: the uniform text says a period not exceeding 30 days, New York’s version uses 14, and your deposit agreement can shorten it further. Check yours.
The Eight Things Your Bookkeeper Needs, and When
Due by the 5th:
- Statements for any account not on a bank feed. The usual holdouts: a personal card you sometimes use for business, a store card, a merchant processor with no direct integration. PDFs, pulled by you from the institution.
- Loan and line-of-credit statements. A loan payment isn’t one expense. It’s principal, which reduces a liability, and interest, which is deductible. Without the statement your bookkeeper is guessing at the split and your balance sheet drifts further from reality every month.
- Credit card statements, even when the feed works. The feed gives transactions. The statement gives interest, fees, credits, and the closing balance to reconcile against.
- Receipts for larger and unusual purchases. See below — the rule is narrower than you’ve been told.
- Payroll reports, if payroll runs outside your accounting file. The period register, the tax liability summary, and any off-cycle or bonus runs. If Gusto or ADP syncs directly, skip it.
- Answers to last month’s open questions. The item that actually holds up your close.
Due the day it happens:
- New accounts, loans, payment processors, or annually renewing subscriptions. A Stripe account that surfaces unannounced in a bank feed six weeks later is a small forensic project. A two-line email costs nothing.
- W-9s from contractors — before the first payment, not in January when you’re filing 1099-NEC forms by the February 2 deadline and one person has gone quiet. Collecting a W-9 from someone who wants to get paid is easy. From someone you stopped working with in April, it isn’t.
Receipts: What the IRS Actually Requires
This is where a lot of confident internet advice goes wrong. The general rule has no dollar threshold: you must keep records sufficient to establish the income and deductions on your return. A $40 expense needs support just like a $4,000 one.
The famous “$75 rule” is real but much narrower than it gets quoted. It lives in the substantiation regulations for travel, meals, gifts, and listed property — Treasury Regulation § 1.274-5 — which require documentary evidence for any lodging expenditure while traveling away from home regardless of amount, and for any other such expenditure of $75 or more. That’s relief inside one category, not a blanket permission slip to bin every receipt under $75, and it never removed the requirement to record what the expense was and why. A statement line reading “AMZN Mktp US” proves you spent money. It proves nothing about the business purpose.
My rule for clients: keep the paper for anything over $75, anything travel- or meal-related, any asset purchase over $2,500, and anything you’d struggle to explain in two years. Photos are fine.
How long: the IRS says three years in most situations, six if you underreport gross income by more than 25%, seven for a worthless securities or bad debt claim, and indefinitely if you file a fraudulent return or don’t file. Employment tax records get at least four years. Seven years of digital storage costs approximately nothing, so keep seven.
The Four Things Only You Can Answer
Your bookkeeper can categorize a Zoom subscription without asking. These four, nobody can answer but you.
Owner draws versus business expenses. Money you moved to your personal account is a draw or a distribution, not an expense, and it doesn’t reduce taxable income. Miscoding these is one of the most common errors I find in cleanup work.
Personal charges on the business card. It happens. The fix is thirty seconds of honesty — “the $312 at Target on the 8th was personal.” The alternative is a deduction you can’t defend.
That one deposit. A loan advance, a refund, a transfer from savings, money you put in personally. Each lands somewhere completely different in your books, and nothing in the bank feed tells them apart. This single item delays more closes than anything else here.
Contractor versus employee. Your bookkeeper needs to know how you’ve classified anyone new — and that’s a legal determination based on control over the work, not a preference. Ask your CPA before the first payment, not after.
What You Should Get Back, and When
This is a two-way agreement. Packet in by the 5th, closed books by the 15th, every month: a profit and loss statement for the month and year to date, a balance sheet as of the last day of the month, a reconciliation report for every account showing the statement ending balance agreeing to the book balance, a short list of open questions, and a note on anything unusual, in plain English.
If you’re getting a P&L and nothing else, you’re getting a third of a close. The reconciliation reports are the evidence the P&L is real, and they’re the deliverable most owners never think to ask for.
How to Handle the Mid-Month Question
You’ll have questions on the 9th. Two rules keep them from derailing the close.
Batch the small ones. Keep a running note and send it once, or save it for the 5th. Eight separate one-line emails cost more of your bookkeeper’s time than a hundred transactions, and that time comes out of your retainer somewhere.
Escalate the real ones immediately. “Can I afford to hire in September.” “Did that $18,000 wire go out.” If a wrong answer costs you money this week, it’s urgent.
The 15-Minute Monthly Routine
Put it on your calendar for the 3rd. Recurring.
Download every statement that isn’t feeding automatically — three minutes. Confirm the month’s receipts are filed or synced — three minutes. Answer every line of last month’s question list, including the ones where the answer is “I don’t remember, here’s the vendor” — five minutes. Scan your bank activity for anything you don’t recognize — two minutes. Send it in one email with the month in the subject line — two minutes.
That’s the job. It only feels bigger because it’s unscheduled, so you’re paying the cost of deciding to do it forty times a month instead of once.
When You Can Ignore Most of This List
I’d rather say this plainly than sell you a system you don’t need.
If you run one business checking account and one business card, both on live feeds, with no payroll, no contractors, no loans, and one merchant processor, your monthly handoff isn’t eight items. It’s two: answer the open questions, confirm nothing weird happened. Four minutes. A bookkeeper sending a solo consultant a twenty-item packet every month is generating work, not doing it. Ask yours which items apply and delete the rest.
The flip side matters too. The month you add payroll, take a loan, open a second entity, or start paying contractors is the month to expand the list — not the following January, when it surfaces as a problem.
Frequently Asked Questions About Working With Your Bookkeeper
What do I need to send my bookkeeper each month?
Statements for any account not on a live bank feed, credit card and loan statements, receipts for larger or unusual purchases, payroll reports if payroll runs outside your accounting file, and answers to last month’s open questions — all by the 5th. New accounts, new loans, and contractor W-9s go over the day they happen.
Do I really need to keep receipts under $75?
Often, yes. The $75 threshold sits in the substantiation rules for travel, meals, gifts, and listed property, and it doesn’t touch the general requirement to keep records supporting every deduction on your return. Lodging while traveling away from home needs documentary evidence at any amount.
How long do I have to keep business records?
The IRS generally says three years, six if you underreport gross income by more than 25%, seven for a worthless securities or bad debt claim, and indefinitely if you file a fraudulent return or don’t file. Employment tax records get at least four years after the tax is due or paid.
What if I don’t remember what a transaction was for?
Say so, and hand over what you do have — vendor name, date, the account it hit. A good bookkeeper can often trace it. What doesn’t work is silence: an unanswered question becomes an “Ask My Accountant” entry, and those accumulate into the mess that gets billed as cleanup later.
Can I give my bookkeeper my bank login instead?
No, and a professional firm won’t ask. Read-only bank access is a standard entitlement at major business banks — visibility without credentials that can move money.
Want This as a Checklist You Can Actually Use?
This works better on paper than in a post you read once. If you want the printable version — the eight items, the deadlines, the four questions, and the receipt rules on one page — grab the Monthly Bookkeeping Handoff Checklist. It’s free, and it’s the one I send my own clients.
If you just realized your bookkeeper has never sent you a question list or a reconciliation report, that’s worth a conversation. Book a free discovery call and I’ll tell you what I actually see — including if the honest answer is that your bookkeeper is fine and the gap is on your side of the handoff.
And if you do your own books, this list still works. You’re just sending it to yourself. Put it on the calendar for the 3rd anyway.