As the leaves start to turn and October settles in, many businesses are gearing up for what can feel like a never-ending tax season. While 1099 reporting may not be the most exciting task on your to-do list, it’s crucial to validate your records early and avoid last-minute scrambles.

5 Steps to Prepare for a Stress-Free 1099 Filing Season

By breaking down your tax prep process into manageable steps, you can avoid the last-minute rush and ensure you’re ready to file when the time comes. Below are the top five things small businesses can do before the end of the year to set themselves up for a stress-free tax season.

  1. Set reminders for key filing deadlines: One of the simplest yet most crucial steps in preparing for 1099 season is to set reminders for all IRS reporting deadlines well in advance. While the deadline to submit 1099 forms to the IRS is January 31st, it’s best practice to schedule multiple reminders. For instance, set an earlier internal deadline to gather all necessary information from your vendors and contractors before the official due date. This extra buffer allows time to resolve any missing details or last-minute issues, ensuring your filings are accurate and on time.
  2. Review regulatory updates: Now is the time to ensure you’re fully prepared for a smooth 1099 filing season by reviewing any regulatory changes at both the federal and state levels. Tax regulations can change frequently, so it’s essential to stay informed about updates that could impact how you file.
    For example, some states may require direct submission of 1099 forms, while others may have deadlines that differ from federal requirements. Overlooking these regulations can result in penalties, so it’s worth the effort to research what applies to your business.
  3. Communicate with vendors and internal staff: Effective and timely communication with both vendors and internal staff is crucial for a smooth 1099 reporting process. Start by sending a reminder to your vendors and contractors, emphasizing the importance of providing accurate and up-to-date information. Request updated W-9 forms from any new or existing contractors whose details may have changed during the year. This ensures you have the correct Taxpayer Identification Numbers (TINs) and addresses well before the filing deadline.
    Internally, provide staff with an overview of the reporting process, assigning clear roles and responsibilities. For small businesses, this may mean confirming who will collect data, validate records, and ultimately file the 1099s. If the company works with an accountant or a payroll service provider, ensure they are fully aware of any changes to your filing process or deadlines.
  4. Test your 1099 reporting process: Before the busy season hits, take time to run a pilot test of your 1099 reporting process. Think of this as a dry run for the real thing, allowing you to identify any gaps or issues in your data well before the pressure of the filing deadline is upon you. Start by pulling a sample of your filer and recipient data. This includes checking for common errors such as missing or invalid TINs (Taxpayer Identification Numbers), outdated addresses, and incorrectly categorized vendors.
    For instance, some vendors may have been classified as independent contractors when they should be categorized differently, or addresses may have changed without updates in your system. These small errors, if not caught in time, can snowball into larger issues, resulting in rejected filings or penalties from the IRS.
  5. Run a Bulk TIN Check: Think of TIN validation like preparing your home before a big winter storm hits. You could wait until the first snowflake falls, but isn’t it smarter to be ready well in advance? With our Bulk TINCheck, you can select a plan tailored to your business needs. With customizable plans built for businesses of all sizes, TINCheck Bulk Match simplifies the validation process by allowing you to upload and verify all your contractor and vendor data in one go.
    Here’s how it works: after selecting your plan, simply upload your vendor, contractor, or customer data into TINCheck. The platform quickly cross-references your records with IRS data and flags any discrepancies, providing you with a detailed report of issues that need correction. You’ll have accurate, IRS-compliant records in no time—and the peace of mind that comes with knowing your 1099 season will go off without a hitch.

A Smoother 1099 Season Starts Today

Procrastinating on 1099 preparation can lead to unnecessary stress and potential penalties. A little effort now will save you time, reduce errors, and give you the confidence that you’re ready to file on time. Start your Bulk TINCheck today and set yourself up for a seamless 1099 season.

Get started with TINCheck Bulk Match today!