The 5-employee contractor's weekly payroll checklist

When you grew from 2 employees to 5, payroll quietly became a 3-hour Sunday-night chore. Here's how to get it back to 30 minutes — with a printable checklist.

When you had 2 employees, payroll was easy. You knew their hours. You wrote the check. Done.

At 5 employees, something flipped. Now there are timecards, a foreman, two job sites, an apprentice who can't remember his own hours, and Sunday night turns into 3 hours of reconciliation. This is the checklist that gets it back to 30 minutes.

The 5 root causes of Sunday-night dread

Before fixing the checklist, name the actual problems:

1. Late timecards. Two guys haven't turned theirs in by Friday afternoon. You're chasing them via text on Saturday.
2. Illegible cards. Carlos's handwriting is so bad you can't tell if Wednesday is 8.5 hours or 8.0.
3. Job-site disputes. The foreman remembers different hours than the journeyman. You're trying to triangulate.
4. Overtime math. One guy hit 47 hours, another straddled two states this week, two were on a federal job. The math gets non-trivial.
5. No source of truth. The card says X. The foreman says Y. The crew member says Z. You're guessing.

If you fix #5 — moving the time-source from paper-and-memory to a digital punch at the moment of work — items 1–4 collapse on their own. But that's a tool decision, not a checklist item. The checklist below assumes you've moved to digital. (If you haven't, see How to switch from paper timecards.)

The weekly checklist

Monday morning (5 minutes)

• Open the dashboard. Confirm everyone clocked in for the week's first shift.
• Skim for outliers — anyone clocked in from an unusual location? Address it before it becomes a Friday discussion.
• If you use schedules: confirm the week is published and crews see it.

Wednesday afternoon (3 minutes)

• Mid-week sanity check: any missing punches, any 12-hour shifts that should have been split?
• If you spot an obvious error, ask the employee to fix it via the in-app correction request, while the day is still fresh in their mind.

Friday end-of-day (10 minutes)

• Confirm every shift has an end-time. Anyone still showing as on-the-clock at 9pm forgot to punch out.
• Review any time-correction requests from the week — approve or reject.
• Check overtime: who's at 38+ hours? Decide whether to keep them on the clock Saturday or send them home.

Sunday evening (15 minutes — yes, really)

• Open the timesheet for the week ending today.
• Spot-check totals against your gut. Anything wildly off?
• Approve the week's timesheets.
• Export to CSV (or PDF for your records).
• Import into QuickBooks Payroll (or your provider) — usually a one-click action.
• Review the payroll preview. Hit submit.

Monday morning (post-payroll, 2 minutes)

• Confirm direct deposits went out.
• Save the CSV/PDF for the archive (good for workers' comp + DOL audits later).
• Note any anomalies for next week's review.

Monthly: don't forget these

• Tax filings: federal 941 (quarterly), state unemployment, local taxes. Most payroll providers (Gusto, ADP, QuickBooks Payroll) auto-file these — but make sure you've authorized it.
• Workers' comp audit prep: save a monthly payroll PDF. The annual audit gets brutal if you don't.
• 1099 contractors: if you used any subs as 1099s, track their pay separately. You'll file 1099-NEC in January for anyone you paid $600+.

Quarterly + yearly

• Quarterly: Form 941 (federal payroll taxes). State unemployment reports.
• Annually: W-2s for employees (by Jan 31). 1099-NECs for contractors (by Jan 31). Form 940 (FUTA annual).
• Year-end review: compare actual labor cost per job to bid labor. Adjust your bid markup for next year.

Pitfalls that catch contractors at 5–15 employees

Misclassifying an employee as a 1099 contractor

The IRS has a 20-factor test. The short version: if you control how/when/where the work is done, they're an employee, not a 1099. Reclassification is one of the most expensive audit outcomes — back payroll taxes plus penalties.

Paying "under the table" for cash overflow

Every contractor has been tempted. It doesn't work — workers' comp won't cover an off-books accident, and any IRS notice means a multi-year unwinding. Don't do it.

Not paying overtime to a foreman

Foremen are non-exempt under FLSA unless they spend most of their week supervising (and rarely doing manual work). Most working foremen still qualify for overtime. When in doubt, pay it.

Approving timesheets without checking

If you rubber-stamp every week, you stop being a check on errors. Spot-checking 5 employees takes 2 minutes. Do it.

Pulling it together

The single highest-leverage move for a 5-employee contractor running paper timecards: switch to digital. Once every punch is captured at the source — by the worker, on their phone — items 1–4 of the dread list above disappear automatically. The checklist becomes the routine, not the firefight.