The holiday rush can bring in more customers and work than your regular staff can handle. Seasonal employees can help you meet this demand, but that extra help comes with additional expenses, tasks and risks.

If you’re hiring for the winter months, maximize your investment. Keep reading to learn how to determine how much extra help you need, tips to find (and keep) reliable employees and how to protect your business and your team with small business insurance through the end of the season.

7 tips for hiring and retaining seasonal employees

Seasonal employees have a short window to learn the job, so planning ahead gives you time to find the right people and train them before your busiest weeks.

1. Estimate staffing needs first

Start by reviewing last year’s holiday sales volume and the shifts where your team was stretched thin. Then check your current employees’ availability, including any planned time off. This can help you identify which jobs need extra support and how many hours you’ll need covered.

Zack Nienaber of Nienaber and Sons Lawn Care in Addyston, Ohio, says his company’s demand changes once the temperatures drop. “Our workload shifts dramatically toward autumn leaf cleanups, seasonal gutter maintenance and winter snow removal preparation,” he explains.

To cover this demand, Nienaber and his staff first review past demand and upcoming work. “We look at historical service demand, recurring commercial contracts and upcoming bookings to determine how many field hands and equipment operators we need to bring on to prevent burnout on our core crew.”

2. Start recruiting early and reach out to returning workers

Finding qualified employees isn’t always easy. The NFIB’s August 2026 jobs report found that 82% of small business owners who were hiring found few or no qualified applicants for the job they were looking to fill.

Give yourself time to recruit, interview and train employees before the increased demand. Marty Babayov, founder and CEO of The Suit Depot, a men’s clothing store in Oak Park, Michigan, starts recruiting well before the holiday orders pick up. “We tend to start looking in early August, and our seasonal workers typically start coming on board in early October,” he says.

Contact reliable former seasonal employees first since they already know your business. You can also ask your current employees for referrals and share openings through local job boards and social media.

3. Be clear about pay and holiday availability

Your job posting should explain the hourly pay, expected start and end dates, typical weekly hours and any required weekend or holiday shifts. If the hours depend on weather or customer demand, explain that to potential employees upfront.

During interviews, ask candidates about specific dates and shifts they’re willing to work. Someone may be happy to work weekends, but already have travel planned for Thanksgiving.

You should also discuss scheduling expectations, including how far in advance you schedule shifts and how employees can request time off. Clear expectations help both sides determine whether the position is a good fit.

4. Prioritize enthusiasm and adaptability

Some seasonal roles require specific experience, while others involve skills you can teach. Once candidates meet the job’s essential qualifications, look for a willingness to learn, adaptability and good communication skills.

DIY manufacturing shop owner April Wilkerson looks for enthusiasm when considering new team members. “Anybody who shows a willingness to want to be on my team and be in my world, I say, ‘Sure, let’s give it a try.’”

During interviews, ask candidates for examples of how they’ve handled changing priorities or busy periods. Questions like “Tell me about a time you had to shift gears quickly at work” can help you assess how they might respond during the holiday rush.

5. Train seasonal employees before the rush

Build time for seasonal workers to learn your systems and procedures before handling a busy shift. Use a short onboarding checklist that covers:

Daily duties
Timekeeping
Customer service
Job-specific safety practices

Prioritize the tasks they’ll perform most often and the situations where mistakes could cause an injury. For example, retail employees may need training on lifting stock and keeping walkways clear.

Babayov starts seasonal hires on less complex tasks and includes year-round employees in the training process. “Clothing involves sizing, matching jackets and trousers, handling garments properly and getting orders right,” he explains. His main challenge is training seasonal employees quickly while avoiding mistakes.

6. Give workers a reason to stay through the season

For Nienaber, employee retention comes down to competitive hourly wages, clear expectations and open communication. “Treating seasonal hands like true members of the team and ensuring they have safe, well-maintained equipment goes a long way,” he says.

Include temporary employees in team updates and check in on scheduling concerns before they become a reason to leave. If your budget allows for it, consider offering employee discounts or an end-of-season bonus with clear eligibility rules.

“A number of our seasonal workers are students, so they really appreciate the flexible work schedules we’ve created,” Babayov says. He also gives good seasonal employees opportunities to return during prom and wedding season in the spring.

7. Prepare for absences and unexpected demand

Plan for the possibility that someone doesn’t show up during your busiest shifts. Identify employees who can cover additional duties after training, and keep track of who’s willing and able to pick up extra shifts.

Pros and cons of hiring for holiday jobs

Seasonal hiring can help you manage a busy stretch, but temporary employees still require an investment in training and supervision.

The possible benefits of seasonal help include:

Extra capacity during peak demand: Additional employees can help you serve customers, fulfill orders and complete jobs that your regular team may struggle to handle on their own.
Relief for existing employees: Sharing the workload can reduce the need for extra shifts and give your core team more room to take planned time off.
Staffing flexibility: Temporary positions let you add support for the weeks or months you need it without committing to year-round positions.
Trial period: Seasonal work gives you the opportunity to assess whether a permanent position could be a good fit.

Potential drawbacks of hiring for the season include:

Costs beyond hourly wages: Recruiting and onboarding new employees requires significant time and resources. Factor these expenses into your budget when deciding whether bringing on additional staff makes sense.
Tax on time resources: New hires need to get up to speed quickly, and experienced staff will need time to train them.
Risk of losing help mid-season: Scheduling conflicts or another job could leave you short-staffed when you need coverage the most.
Uncertain demand: Lower-than-expected sales or changes in the weather could leave you with more scheduled staff than work available.

Pay rates and overtime pay for seasonal workers

Set your seasonal pay rates by considering the job’s responsibilities, required experience and what other employers in your area pay. For the retail trade, The Bureau of Labor Statistics reports a median hourly wage of $26.38 in September 2026. This figure includes regular and seasonal employees, so use it as a starting point rather than a recommended holiday hiring rate of pay.

Seasonal employees generally have the same wage and hourly protections as regular employees. Under the Fair Labor Standards Act, nonexempt employees must receive at least one-and-a-half times their rate of regular pay for working more than 40 hours in a workweek. For example, an employee whose regular rate is $18 an hour would earn $27 an hour in overtime, so working 45 hours would bring their gross weekly pay to $855.

Track hours throughout the week so additional shifts don’t create unexpected overtime costs. If you offer an end-of-the-season bonus, check with your payroll provider about whether it must be included in the employee’s regular pay rate when calculating overtime.

Business insurance requirements for seasonal hiring

Bringing on seasonal employees introduces new risks for you, your business and your employees. If someone gets hurt on the job, workers’ compensation insurance could help cover medical treatments and a portion of lost wages if there’s a covered workplace injury or illness.

Seasonal and part-time employees may need to be covered under your state’s workers’ compensation requirements. Check with the workers’ compensation agency in your state before hiring new workers, since adding holiday staff could bring your business above the applicable employee threshold and require you to carry coverage.

If your business already has workers’ comp coverage, let your insurance provider know about any changes to your payroll and the kinds of duties seasonal employees will perform. If you hire through a staffing agency, confirm who provides workers’ compensation coverage and how workplace injuries should be reported.

Business insurance is just one aspect of preparing employees for workplace risks. Coverage is important, but it should sit alongside safety training and clear reporting procedures. Show seasonal employees how to safely use equipment and make sure they know how to report an injury.

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