The start of a new year is always very busy. This is especially true for small businesses as they are juggling setting goals and compliance deadlines. That is why we have come up with a list of key dates in the first few months of the year to put on your calendar. Keeping these in mind early will lead to a more organized start to the year.


January kicks off tax season and there are several deadlines in the first few months of the year. January 31st is the deadline for all businesses to send out Form W-2 to employees and Form 1099-MISC to vendors and contractors. If these are not filed by the end of the month then the employer will face penalties. 

It is important to work closely with your payroll provider to make sure all of these deadlines are met on time. Also, confirm with payroll how employees will be receiving their W-2. That way they will know to look for it electronically or in the mail. This helps to avoid any confusion.

January is also the start of a new benefits year. While there are no deadlines, it is good to keep in mind in case employees have questions about deductibles, coverage, etc.


Employees wishing to claim exempt status for federal tax withholding in 2020 must file a new Form W-4 by February 15th. This will determine how much is withheld in taxes for 2020. Any previous form they filed will expire so it is important to send a reminder and let employees know that this deadline is approaching. 

Employers with over 50 full-time employees are required to submit Forms 1094-C and 1095-C by February 28. Employers with less than 50 full-time employees must send in Forms 1094-B and 1095-B. These documents help employees complete the health coverage portion of their tax return.


Large businesses and certain industries are required to post the previous year’s OSHA summary of injuries and illnesses (Form 300A) and submit them by March 2. While this does not apply to all employers, it is good to understand how it may apply to your business. 


April 15th is the deadline for individuals to file their taxes. Although this is not a deadline for the business, it’s good to keep in mind since it impacts all of your employees.

This is not meant to be a completely comprehensive list but just a few key deadlines to be aware of. At Alpine Talent Partners we help businesses demystify compliance requirements and deadlines so that they can focus on developing strategies and goals for their best year yet.