Don’t Let January Blindside You: The December Checklist for a Smooth 2026 Kickoff

beth2340
1 day ago
3 min read

There’s a special kind of chaos reserved for the company that stumbles back from the holidays only to discover:

Payroll is short because holiday pay wasn’t coded correctly
Half the team missed open enrollment and now wants a “do-over”
No one knows what they’re supposed to be working on because goals weren’t set
Bonuses are still a mystery and the rumor mill is working overtime

Avoid all of that. Spend two focused hours in December (yes, this month) and January will feel like a normal month instead of a five Mondays in a row.

1. Lock Down Year-End Bonuses (Calculations + Communication)

Finalize the bonus formula and run the numbers.
Decide when bonuses will be paid (with the December 31 paycheck is most common).
Draft the individual bonus letters or spreadsheet now — even if the final sign-off comes in mid-December.
Send a short “Bonuses are on track — you’ll hear exact amounts by December 20” email in early December. Silence breeds resentment; a tiny breadcrumb of certainty kills it.

2. Payroll & Holiday Pay Audit

Confirm with your payroll provider exactly which days are being paid as “holidays” and at what rate (time-and-a-half, double-time, etc.).
Verify that floating holidays or extra December 24/31 closures are correctly loaded.
Run a test payroll for the December 31 pay period the first week of December.
Catching errors on December 6 is easy; catching them on January 3 is a nightmare.

3. W-2 & Tax Document Timeline

Confirm with payroll provider when W-2s will be available (electronic and paper).

Decide if you’re mailing paper W-2s to terminated employees or using electronic-only with consent.

Put the distribution date on your calendar now and block an hour the week of January 20 to review for errors before they go out.

4. Open Enrollment & January 1 Benefit Changes

Send the “Last call — open enrollment ends December 15” reminder (with a screenshot of how to log in).

Export a list of employees who still haven’t completed enrollment and have their managers give a gentle nudge.

Create a one-page “What’s changing January 1” summary (new deductible, 401(k) match increase, HSA contribution limits, etc.) and email it December 20.

5. 401(k), HSA, and FSA Reminders

Send the annual “Max out your 401(k) — you have two pay periods left” email.

Include the exact dollar amount needed per paycheck for common salaries.

Remind people that 2025 FSA dollars expire (or get forfeited) if not spent — include a link to eligible expenses.

6. Set Q1 Goals and Priorities (Yes, in December)

Waiting until January 15 to set goals guarantees a sluggish January and a panicked February.

Do this instead:

Leadership off-site or two focused meetings in late November/early December.

Cascade company goals → department goals → individual goals by December 20.

Put the final written Q1 priorities in a shared doc and tell everyone: “This is what success looks like when we come back January 2.”

7. Schedule the January “Re-Entry” Meeting Now

Block 60–90 minutes on January 5 or 6 for a full-company (or department) kickoff.

Agenda:

Quick wins from Q4

Celebration of the previous year

Clear Q1 priorities

Reminders about benefit changes

Open floor for questions

People return from break with clarity instead of dread.

The Bottom Line

January chaos is optional. Two hours of planning in November or December saves dozens of hours of firefighting in January — and protects your reputation as a place that actually has its act together.

Here’s to starting 2026 strong — without the traditional January heart attack.—

McPherson | Berry - We turn HR headaches into competitive advantages for growing organizations.