The holidays may be a boon for business, but they’re also a magnet for risk. Small business owners face everything from staffing shortages and customer surges to cybersecurity threats, weather disruptions, and seasonal chaos.
To cut through the noise and get real guidance, I spoke with Rebeccah Slate of Travelers, who shared the essential steps every business should take to stay safe, resilient, and ready for whatever the season brings. Slate’s advice doesn’t just apply to this holiday season; it’s critical to protect your business year-round.
Rieva Lesonsky. How can I ensure the safety of my workers and customers during the busy holiday season and beyond?
Rebeccah Slate: Many businesses see an influx of new and/or temporary staff during the holiday season. According to the Travelers Injury Impact Report, 46% of all injuries at small businesses between 2020 and 2024 involved first-year employees, highlighting the importance of comprehensive training and robust safety protocols year-round. Make time to fully train everyone on your staff in safe operations and the importance of protecting the safety of your customers.
For customer safety, be vigilant about weather-related hazards such as slippery sidewalks. Make sure holiday decorations don’t obstruct paths or create fire risks. Regularly review emergency procedures and maintain clear communication with your team to foster a safe environment for everyone.
Lesonsky: How should I prepare my business for inclement weather during the holiday season and throughout the winter?
Slate: Icy winter weather can increase the risk of slip-and-fall accidents and property damage. Regularly check weather forecasts to stay informed, develop a clear plan for snow and ice removal, and make sure your staff members know their responsibilities. Communicate with landlords and contractors about maintenance requirements and establish protocols for potential power disruptions.
Lesonsky: What steps can I take to protect my business from cyber threats during the holidays?
Slate: Cyber threats are a top concern for businesses of all sizes, as highlighted in the 2025 Travelers Risk Index. For the professional services sector, security breaches and unauthorized access to financial accounts are major worries. In retail, the theft of customer records is a significant danger.
To mitigate cybersecurity risks such as unauthorized access, information and financial theft, ransomware, and employee errors, implement multifactor authentication, regularly back up your data, and promptly patch vulnerabilities. Develop an incident response plan, and consult your insurance agent about cyber coverage, which often provides preventive measures and pre-breach services. Remember, take action now and remain vigilant throughout the year.
Lesonsky: What should I consider when hosting special events or setting up holiday displays?
Slate: Special events and displays introduce unique risks. Secure decorations, don’t create trip hazards or block emergency exits, and be mindful of fire hazards from lights and candles. If you’re hiring outside vendors, verify their insurance coverage and require them to comply with your safety standards. Review contracts carefully to understand your liability and their responsibilities. Additionally, check your insurance coverage to see how well protected you are against any event-specific risks, and consider additional coverage if necessary.
Lesonsky: What should I know about setting up a temporary space at a holiday market?
Slate: If you’re setting up a temporary space, discuss coverage with your insurance agent. General liability coverage from your main location often extends to temporary spaces, protecting against issues like slip-and-fall accidents. But consider additional coverage if you regularly participate in holiday markets or pop-up events.
Lesonsky: How should I prepare my business if I plan to close for an extended period during the holidays?
Slate: For businesses like professional services that may close for extended periods during the holidays, it’s important to secure your premises and assets. Be sure that all equipment is turned off and unplugged and that security systems are activated. If you are in a cold climate, maintain a minimum temperature of 40 degrees F in key areas of your building to help avoid frozen pipes. Communicate your closure dates to clients well in advance. And review your insurance policy to understand coverage during closures—consider additional protection for any specific risks associated with being closed, such as theft or vandalism.
Lesonsky: What should I do if I need to file a claim during the holiday season?
Slate: If you need to file a claim, document the incident thoroughly. Take photos or videos of any damage and gather all relevant information, such as receipts, inventory lists, and witness statements. Contact your insurance agent promptly to report the incident and provide all documentation as soon as possible. Being organized and detailed will preserve evidence and help expedite the claims process.
Rieva Lesonsky is the founder of Small Business Currents, a content company focusing on small businesses and entrepreneurship. You can find her on Twitter @Rieva, Bluesky @Rieva.bsky.social, and LinkedIn. Or email her at Rieva@SmallBusinessCurrents.com.
Photo courtesy: Getty Images for Unsplash+
