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In the early days of Kristen David’s law firm, she told staffers they could all take off the day after Thanksgiving. But before the holiday, they learned an upcoming trial would start Monday, right after the long weekend.

“I had given them the weekend off. They had made travel plans and weren’t even going to be in town,” said David, who ended up working solo through the weekend to be sure the firm was ready for the trial.

Holiday staffing can be one of a small business owner’s biggest stressors — even companies that aren’t retailers or restaurants can have a year-end busy season, just when employees all want to take time off. Accounting and other financial advisory firms, for example, must get work done for clients by Dec. 31, and the nature of their work doesn’t allow them to use temporary help. Companies can also have an unexpected crisis or project that can force an owner to change holiday plans, a hard lesson that can affect a company’s vacation policy going forward. And owners can discover they’re vulnerable to staffing issues at other companies.

David learned a lesson about managing staffers’ expectations.

Now, “we let the team know that while we’d love to give everyone the Friday off after Thanksgiving, or Monday after a holiday as an extra bonus, we’ll have to wait until just before the holiday to determine the final schedule,” she says.

The experience also taught David, who now works as a business coach based in Seattle, that everyone couldn’t be out of the office at the same time. The firm changed its vacation policy and encouraged staffers to request just a few days off so everyone could have a chance to be off during the holidays.

While some holiday staffing issues can’t be predicted, owners can lessen the likelihood of problems by setting expectations well in advance, says Kate Zabriskie, president of Business Training Works, a company that offers management training.

“People don’t like being told one thing and then finding out it’s not so,” Zabriskie says.

The clients at Dawson Whitfield’s graphic design company include entrepreneurs who need logos created ASAP, even if the holidays are in full swing.

“Right when everyone in the office wants to ramp down for vacation, our customers are ramping up to finally follow that New Year’s resolution of launching a business,” says Whitfield, owner of Toronto-based Looka.

When Whitfield hires a staffer, he tells them that it will be hard to take time off in December. He does let employees take some days, but of course everyone wants the prime days, a common problem at companies of all sizes. His solution is to remind staffers that designing logos is a key part of the company’s mission and, rather than dictating a solution, he asks them to work out a schedule for time off.

“When they can be part of the solution, and the solution comes to them, it’s more palatable to them,” he says.

Many small businesses that provide specialized or professional services can’t bring in temporary staffers the way retailers, restaurants and delivery services do. Architecture, accounting and law firms, for example, tend to work on an ongoing basis with clients, and freelancers or temporary employees won’t be able to just jump in and take over the work. Moreover, even companies that can use temporary help can struggle to find it because of the shrunken labor pool, a result of low unemployment.

Owners can find out the hard way that they can be hurt by other companies’ staffing problems. Chase Fisher has learned he needs to be concerned not only about having enough people in his eyewear retailing business but also about the number of employees in the companies he deals with.

Fisher, owner of Blenders Eyewear, has realized that several months before Black Friday, he needs to meet with the companies that take the orders and pack and ship his sunglasses and ski goggles. If those companies are understaffed, then deliveries of his merchandise will be delayed and customers will post negative reviews online about his business.

Fisher, who has an internet business and a physical store in San Diego, expects nearly two-thirds of his holiday customers to be first-time shoppers. If an order is shipped late, “that’s something that will break your trust immediately,” he says.

Small businesses that rely on freelancers or independent contractors to get their work done can also struggle with staffing issues — but these are workers an owner has no control over.

Robyn Flint hires building contractors to fix up houses that have been damaged in natural disasters or fires. Her company, Property Wise, is based in Bedford, Virginia. Some of the work is done for owners who need to get back into their homes; Flint also needs rehabilitation work on houses she buys and plans to resell.

But, she says, “during the holidays it is hard to find people to keep the work going.”

Most of the contractors are self-employed and make their own hours, and many decide to take the holidays off. Some leave in the middle of a job. Meanwhile, Flint has frustrated homeowners waiting, or she’s paying interest and taxes on houses that can’t be sold until she can get contractors to renovate them.

“We’re at their mercy or we have to find someone else if we can,” she says.

It’s especially a problem in the months after a hurricane or tornado damage.

“There’s generally a lot of people at one time needing the same resources,” Flint says.

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