HR Compliance Calendar: Deadlines for Small Employers

The first compliance deadline I missed was a state new hire report. It was worth twenty-five dollars in penalty, which is not the point. The point is that I did not know the obligation existed until months later, and there was no reason I would have. Nobody sends you a list of what you now owe when you hire your fourth person.

A compliance calendar is that list. Remembering the deadlines you already know about is the easy part, and most people manage it. The hard part is knowing which deadlines exist for a business your size, in the states where your people actually work, before the date rather than after it.

Below is a working calendar you can download and edit, followed by an explanation of which parts apply to you. It is built for a small business with no HR department. Several obligations on standard published calendars start only at a certain headcount, so this one marks each with its threshold, and you can ignore what you have not triggered.

The Calendar

Three sheets: the annual calendar month by month, a headcount filter showing which obligations you have actually triggered, and the recurring tasks that do not sit on a fixed date. Download it, delete the rows that do not apply to you, and fill in the owner column.

Two notes before you use it. First, several federal deadlines move to the next business day when they fall on a weekend, so verify the exact date each January against the agency rather than assuming last year's date.

Second, the calendar covers the common federal obligations, and state obligations appear in it only as generic reminder lines. The state layer is yours to add, as discussed further down, and for most small businesses it is the larger half.

What an HR Compliance Calendar Is

Two related calendars are easy to mix up with this one. A payroll calendar covers pay dates and deposit schedules. A tax calendar covers filings. An HR compliance calendar includes both of those and adds the employment-specific obligations that sit outside finance entirely: safety postings, benefits notices, I-9 reverification, handbook distribution, and the state-level rules that change every January.

The term compliance calendar on its own is used across several fields that have nothing to do with employment. Financial services firms, environmental and safety teams, and corporate registered agents all maintain calendars by that name covering entirely different obligations. This guide is specifically the HR and employment version.

The authoritative sources for the dates themselves are the agencies that set them. The IRS employment tax due dates page covers payroll filings and information returns, and OSHA, the Occupational Safety and Health Administration, publishes the recordkeeping and submission deadlines.

Which Deadlines Apply at Your Headcount

Employment obligations switch on at defined headcounts, so the deadlines that apply to you depend on how many people you employ. Most published calendars skip the headcount filter, and it is what separates a useful document from an intimidating list of things that mostly are not yours.

One boundary is worth stating precisely, because published calendars get it wrong. OSHA recordkeeping switches on above 10 employees, not at 10: 29 CFR 1904.1 partially exempts any company that had 10 or fewer employees at all times during the previous calendar year, and the count covers the entire company rather than one location.

Two counting notes. Part-time employees generally count toward these thresholds, so a business with eight full-time and six part-time staff is usually at fourteen rather than eight. And several thresholds look at the count across a period rather than on a single day, which means a seasonal peak can bring you into coverage for a whole year.

The Year, Quarter by Quarter

The compliance year is lopsided: the first quarter is by far the heaviest, and the second is nearly empty. Knowing that shape lets you plan the work rather than react to it.

Q2 is the time for voluntary compliance work. The handbook review, the I-9 audit, the contractor classification check, and the exempt status review all belong in April through June, because that is the only stretch of the year with genuine slack. Attempting any of them in January guarantees they do not happen.

The Deadlines Most Often Missed

The deadlines most often missed are not the obvious ones, since nobody forgets payroll. They are the ones that sit outside the rhythms a small business already runs on, like these six.

The pattern across all six: they are annual or event-triggered rather than monthly, and nothing in the normal operating rhythm surfaces them. Payroll happens every two weeks, so it self-corrects. A notice due once a year before October 15 has no mechanism at all except a calendar entry somebody made deliberately.

The OSHA posting window is worth pinning to the regulation itself. 29 CFR 1904.32 sets the February 1 posting deadline and the April 30 end date, and it requires a company executive to certify the annual summary before it goes up. OSHA treats the posting as mandatory in a year with no recordable cases as well.

The I-9 case stands out because it has the shortest fuse. The USCIS employer handbook puts Section 2, your review of the documents a new hire presents, within three business days of the first day of employment. A hire on a Monday leaves you until Thursday.

Building Your Own in an Hour

An hour of work turns the downloadable calendar above into your own. It is a starting point rather than a finished artifact, because the state layer and the ownership assignments are specific to you.

Resist making it more elaborate than this. A spreadsheet with a date, an obligation, and an owner, reviewed quarterly, outperforms a sophisticated system nobody updates. Compliance calendars rarely fail for lack of detail. They fail because people stop using them.

The State and Local Layer

For a small business, the state layer is usually both larger and more volatile than the federal one. Federal deadlines move by a day or two when a date falls on a weekend and otherwise stay put for years. State obligations do not behave that way.

Paid sick leave deserves separate attention because it is the state obligation that changes most often and the one most likely to apply at any headcount.

What Happens When You Cross a Threshold

Growth changes your compliance obligations, and it does so silently. Nothing notifies a business that it has become subject to FMLA. This is why the calendar needs a headcount check rather than only dates.

The fifty-employee transition needs particular attention, because both obligations it triggers are substantial and both require preparation before any filing date arrives.

ACA applicable large employer status turns on the average for the prior calendar year, counting full-time and full-time-equivalent employees, which the IRS applicable large employer test sets out in full. You can become an applicable large employer on a headcount you no longer have, so check the calculation rather than your current count.

The fifteen-employee transition is quieter and arrives sooner. It brings anti-discrimination obligations that have no filing date attached, which is precisely why they are missed: nothing is due, so nothing prompts you.

The hundred-employee row is the one in flux. The EEOC sets each EEO-1 window itself, and its data collections page still gave no opening date for the 2025 collection in October 2026. A proposed rule published July 23, 2026, would remove the EEO-1 requirement entirely.

Federal contractors with 50 to 99 employees have their own change to note. A Labor Department final rule rescinds their separate EEO-1 duty under the contractor rules at 41 CFR 60-1.7, effective October 26, 2026.

What Missing a Deadline Costs

Penalties vary widely by obligation and most scale with delay, which makes a late filing considerably cheaper than an ignored one.

The information return figures are published and worth knowing before January. According to Rev. Proc. 2025-32, the IRS revenue procedure that publishes these amounts, a late W-2 or 1099-NEC due in 2027 costs $60 a form if corrected within 30 days, $130 if corrected by August 1, and $340 after that.

Intentional disregard is priced differently: at least $690 a form, or 10 percent of the amounts that should have been reported if that is more, and the IRS information return penalty schedule sets no maximum for it. The IRS republishes the tiers each year, so check the current row before you rely on a figure.

State new hire reporting sits at the cheap end, but its penalty is charged per hire. The federal statute, 42 USC 653a, lets a state charge up to $25 for each hire not reported on time, rising to $500 where the employer and the employee agreed not to report. The statute also caps the reporting window at 20 days after the hire.

The pattern to remember: almost none of these are charged once. They are charged per form, per employee, per deposit, or per day. A process error affecting every employee produces a penalty affecting every employee, which is why a small business can accumulate a meaningful number from a single oversight.

Voluntary correction programs exist for several of these and generally cost far less than having an agency find the problem first, which is an argument for auditing rather than hoping.

Keeping It Current

A compliance calendar built once and never revisited becomes wrong in about a year. Three things change it: your headcount, the states where you have people, and the law itself.

Use primary sources for verification. The IRS, the Department of Labor, and OSHA publish the authoritative dates, and each state labor department publishes its own. Vendor calendars, including the one on this page, are useful for orientation but should not be your source of record for a filing date.

Where employment law changes come from

Employment law updates reach a small business from four directions. Federal agencies issue rules and guidance. State legislatures and labor departments change wage, leave, and scheduling rules. Cities add ordinances above their state, and courts vacate or revive rules that were already on your calendar. Watching only the federal layer misses most of what will actually reach you.

The routine is smaller than that list suggests. Read the Department of Labor news releases and the EEOC newsroom once a quarter, check your states in the same sitting, and set a note in November for the changes landing on January 1. Labor law news that does not move a date, an amount, or a line in your handbook needs no action from you.

The part that does not scale by hand is the event-triggered work: I-9 reverification dates, new hire reporting within days of a start date, and threshold changes as headcount moves. FirstHR covers the hiring end of it: the I-9 and the new hire report can go on each hire's onboarding task list with due dates, and a stored work authorization document keeps its expiry date in the employee file.

Frequently Asked Questions