Contractor bookkeeping checklist: weekly, monthly, yearly

Most bookkeeping problems in a contracting business are not caused by doing something wrong. They are caused by something not being done at all — for long enough that it turns into a project.

This is every recurring task, grouped by how often it has to happen. The ones marked ⚑ are the ones that cost the most when they slip, because the damage compounds quietly and surfaces all at once.

Every week

• Code every transaction to an account and a job. Card swipes, bank payments, supplier bills. A receipt is easy to place on Friday and close to impossible to place in six weeks.
• Attach receipts with the job name written on them. Photograph them the day they happen.
• Enter supplier and sub bills as they arrive, so what you owe is visible before it is due.
• Send invoices for work completed this week — including change orders. Unbilled work is the cheapest money you will ever lose.
• Record labor hours by job from timesheets or the scheduling app.
• ⚑ Collect a W-9 and insurance certificate from any new sub before their first payment. See who needs a 1099.
• Check deposits received are recorded against the right job, as a liability rather than as income.

Every month

• ⚑ Reconcile every bank account, card, loan and line of credit to its statement. This is the step that turns entries into books. See QuickBooks does not match your bank if one will not balance.
• ⚑ Reconcile payroll liabilities — what payroll says was withheld and owed, against what was actually deposited and filed. A missed deposit found in a month is an inconvenience; found at year end it is a serious problem.
• Review receivables ageing and chase anything past due, oldest first. See when a customer will not pay.
• Review payables — what is due, what is disputed, and any early-pay discounts worth taking.
• Update the retainage report — held by job, oldest first, with release conditions. See retainage explained.
• Run job cost reports on completed and open jobs. Which ones made money, and which drifted from the estimate.
• Update the WIP schedule if any job runs longer than a month. See WIP schedules.
• Reconcile supplier statements against the bills you entered.
• Record owner draws and contributions properly, not as expenses.
• File sales tax if your state or volume puts you on a monthly schedule.
• Read the P&L and balance sheet, together. See how to read your P&L and how to read a balance sheet.
• Close the period in your software so last month cannot be changed by accident.

Every quarter

• ⚑ Set aside and pay estimated taxes in consultation with your CPA. See quarterly estimated taxes.
• File sales tax if you are on a quarterly schedule.
• Confirm payroll tax returns were filed and accepted, even if a payroll provider files them. Trust, then check.
• Review job types and pricing against job cost results. Is any category of work consistently underperforming its estimate?
• Check insurance certificate expiries for every active sub.
• Review the cash flow forecast for the next quarter, including slow seasons and retainage release dates. See the cash flow forecast guide.

Every year

• ⚑ Issue 1099s to subs who need them, by the January deadline. With W-9s collected all year, this is a report, not a project. See the 1099 deadline guide.
• Issue W-2s to employees, through your payroll provider.
• Count truck stock and inventory if you carry meaningful amounts. See truck stock and inventory.
• Update the fixed asset list — equipment and vehicles bought, sold or scrapped.
• Prepare for the workers comp and general liability audits with payroll by class and sub certificates ready. See the workers comp audit guide.
• Hand your CPA a clean year-end package. See what your CPA needs at year end.
• Set next year's budget from this year's actuals. See a one-page annual budget.
• Review your own pay against what the business can actually support. See how much should I pay myself.

The three that matter most

If you do nothing else on this list, do these, because they are the ones that compound into real money and real trouble:

1. Reconcile the bank every month. Without it, nothing else in the books is verified.
2. Reconcile payroll liabilities every month. This is the late payment that can follow you personally.
3. Collect W-9s before the first payment. Every January 1099 problem starts with a March payment made without one.

If the list is already behind

Start with the current month and work forwards, then catch up the backlog. Doing it the other way round means the current month falls behind while you fix the old ones. See catch-up bookkeeping for how that usually goes — it is almost always smaller than it feels.

General information, not tax advice. Filing frequencies and deadlines depend on your state, your volume and your CPA's advice.