For many small business owners, holiday planning used to come with a familiar assumption: when customers arrive in greater numbers, add more people to the schedule. This year, that playbook may need a rethink.
Recent survey data shows the share of small business owners trying to hire fell five percentage points from August to September. Among those still looking, 45% said they received few or no qualified applicants. And labor quality or availability is now the top operating problem for roughly one in four owners.
The seasonal hiring picture is tightening, too. Retailers are projected to add about 450,000 seasonal roles this fourth quarter, around 17% fewer than in 2024. More businesses are leaning on automation, existing employees, and on-demand workers instead of building large temporary teams.
That doesn’t mean the season is lost. It means winning may depend less on finding a perfect stack of new hires and more on making your business easier to staff, smoother to run, and better at keeping good people. Here’s how to prepare.
Start by redesigning the job, not reposting it
When a role goes unfilled, it’s tempting to copy last year’s job description and post it again. But if applicants aren’t showing up, or don’t have the skills you need, the role itself may need a closer look.
Take a typical seasonal position and break it into the actual work: greeting customers, restocking, packing orders, handling checkout, responding to messages, or closing the shop. Which tasks require training or judgment? Which can be taught quickly? Which could be simplified, combined, or handled by a tool?
Then build a role around the work you truly need covered. A focused position with clear duties and predictable shifts can be more appealing than a vague “help wherever needed” job. It can also help you identify people with transferable skills rather than searching for someone who checks every box on an old list.
Be honest about the schedule, expected pace, training, and pay from the beginning. Clear expectations help applicants decide whether the job fits, and make it less likely that a new hire will leave after discovering the role is different from what they imagined.
Cross-train the people who already know your business
Your current team has something a brand-new seasonal worker doesn’t: familiarity with your customers, products, and daily rhythms. Cross-training helps you use that experience more flexibly when the rush hits.
Choose a few essential tasks and make sure more than one person can handle each. A shop employee might learn basic online-order packing; a studio assistant might learn how to greet walk-ins; a team member who usually handles customer messages might be trained to cover checkout during the busiest hour.
Keep training practical. A short checklist, a quick demonstration, and a chance to practice during a quieter shift can make a task feel manageable. Don’t assume that “shadowing” once is enough: ask the person to try the task themselves and check that they know when to ask for help.
Cross-training shouldn’t mean quietly piling extra work onto your most dependable employees. Talk through the added responsibilities, adjust schedules where you can, and recognize the effort. The goal is a team with more flexibility, not a small group carrying an invisible second job.
Use on-demand help for the peaks, not as a substitute for a plan
Not every business needs another person for an entire season. Some need coverage for a handful of busy evenings, delivery surges, weekend events, or a particular step in the order process.
Think about when demand actually spikes and match help to those moments. On-demand or temporary workers may be useful for defined, short-term needs, such as event setup, packing, or extra customer-service coverage. Make the assignment specific, explain what success looks like, and identify one person who can answer questions.
Before adding flexible labor, check your local rules and responsibilities for hiring, classification, scheduling, and safety. A quick staffing fix should not create confusion about who supervises the work or what protections apply.
Let AI take some of the admin off your team’s plate
A separate Federal Reserve survey found that small firms already using AI were more likely to expect employment growth than firms that weren’t using it. That’s a measure of expectations, not proof that AI automatically creates jobs or boosts sales. Still, it points to a useful way to think about the technology: it can help a business do more without asking every employee to spend extra hours on paperwork.
Start with repetitive, low-risk admin work. Depending on your business and the tools you use, AI may help draft routine customer replies, summarize notes, organize product descriptions, or create a first pass at a staff checklist. Scheduling software may help you see uncovered shifts sooner. Simple templates can reduce the time spent answering the same questions or rewriting the same instructions.
Keep a person in charge of the final review. Check customer-facing messages for accuracy and tone, avoid entering sensitive customer or employee information into tools that haven’t been approved for that use, and make sure staff know when AI is assisting them.
The best test is practical: does a tool save time without creating more corrections, confusion, or customer frustration? If not, it isn’t helping your team stretch further.
Recruit earlier, and make it easy to say yes
A cooling hiring market doesn’t make timing less important. It makes waiting riskier. If you know your busy weeks, write down the coverage you’ll need now rather than beginning the search when the calendar is already full.
A strong seasonal posting answers the questions applicants are likely to have: What will I do? Which days and hours are available? How much training will I receive? When does the role begin and end? How quickly will you follow up?
Move promptly when someone looks promising. A long, confusing application process can cost a small business a good candidate, especially when the role is temporary. Keep the steps proportionate to the job, communicate clearly, and give applicants a realistic picture of the work.
You can also make the opportunity more attractive without making promises you can’t keep. Consistent shifts, a respectful manager, useful training, and a clear end date all matter. For some candidates, knowing what their schedule will look like is as valuable as another perk.
Treat retention as part of your growth plan
Hiring gets attention because it’s visible: a job post, an interview, a new face on the schedule. Keeping a capable person can be quieter, and just as important. When an experienced employee stays, you preserve customer knowledge, reduce retraining, and give your team more confidence during the busiest weeks.
Check in with your team before the rush. Ask what usually gets hectic, where instructions are unclear, and what would make the season more manageable. Share schedules as early as possible and give people a clear way to flag conflicts. During the season, notice good work specifically: a thoughtful customer interaction, a clean handoff, or someone helping a teammate learn a new task.
If the budget allows, consider a modest seasonal completion bonus or another clear form of recognition. If it doesn’t, reliability still counts: honor agreed schedules, provide breaks, and avoid treating last-minute overtime as the default solution.
Build the season around the team you can support
This holiday season may bring fewer available applicants and fewer seasonal roles across retail. For small businesses, the answer isn’t to simply expect the existing team to absorb everything. It’s to make deliberate choices: simplify roles, cross-train thoughtfully, bring in flexible support where it fits, and use technology to reduce avoidable admin.
Most of all, plan around the people who make your business work. A clear job, a fair schedule, useful tools, and a workplace where effort is noticed can help you serve customers well, even when hiring doesn’t go as expected. The strongest holiday plan isn’t necessarily the one with the most people. It’s the one that helps the right people do their best work.
