Holiday Business Planning: Prepare Without Falling Behind

By Sarah Beth Herman, MBA, Founder & CEO, Dentistry Support®

Some business owners are about to lose two months of productivity, and they have already started explaining why. Thanksgiving is coming. Christmas is around the corner. Employees are requesting time off, customers are changing their schedules, and work that mattered in September suddenly becomes something everyone will “deal with in January.”

I love the holidays. I want business owners and employees to spend time with family, celebrate, and enjoy what they worked hard for all year. But preparing for the holidays is different from letting the business become unproductive because the holidays are coming.

That is what I want to talk about in this week’s Dentistry Support® FREE TRAINING. You do not have to choose between a business that serves its customers and a team that gets to enjoy the season. You do have to prepare before the calendar begins making the decisions for you.

Whether you own a dental practice, a service company, or a seasonal retail business, holiday business planning means preparing for the work ahead: cash, coverage, margins, customer communication, and deadlines before December 31.

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Holiday Business Planning Starts Before the Slowdown

Some businesses experience a real slowdown during the holidays. Others have a busy season. Many experience both: customers and employees are less available on some days, while demand rises on others. The calendar changes how work happens, but it does not decide whether your team can stay focused.

Two older surveys illustrate why it is a mistake to assume everyone responds the same way. In a 2019 Robert Half Technology survey, 52% of employees said they expected to shop online at work or on a company device during the holiday season; 44% of those respondents said the shopping interfered with productivity [1]. In a separate 2018 Accountemps survey, 65% of professionals said they got more work done during the holidays [2].

Those surveys are several years old and should not be treated as a current forecast for every workplace. The useful point is that employees’ experiences differ. Some people are distracted by outside commitments. Others are especially focused because they want to finish work before taking time off. Your job is to give the team clear priorities and realistic workloads so both groups can do their jobs well.

That does not mean canceling holiday vacation or making people feel guilty for wanting time with family. It means deciding what must be covered, communicating deadlines, and giving employees a reasonable plan for the work that remains.

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Protect the Cash You Need to Operate

If there is one financial review to do before the holiday schedule gets tight, it is your cash position. Revenue and production tell you something about activity. They do not tell you exactly how much money will be available to operate the business after payroll and expenses are paid.

Look ahead at the next eight weeks. List the payroll dates, taxes, vendor invoices, rent, insurance, bonuses, annual subscriptions, inventory purchases, and holiday-related expenses you already know are coming. Then estimate the cash you reasonably expect to collect. The Small Business Administration recommends using cash-flow projections to track capital and anticipate future needs [4].

Use realistic timing. If a customer has paid late before, do not build the plan around the hope that this time will be different. In a dental practice, review insurance claims and patient balances that still need follow-up. In another service business, check invoices, deposits, and outstanding renewals. Put the next action beside each important receivable.

The question is not only, “How much did we sell?” Ask: What money is actually available? What obligations are due before the next major collection? What happens if a few payments arrive later than expected? If cash may be tighter than you planned, it is better to learn that now than in the week before Christmas.

A cash review is not an invitation to panic or stop every purchase. It is a way to make deliberate choices while you still have time. If a forecast shows a shortfall, decide what information you need, which expenses can be rescheduled, and whether you should speak with your accountant or lender.

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Finish the Holiday Staffing Plan Before People Leave

Start with the schedule, but do not stop there. Who has requested time off? Who is available during Thanksgiving week, Christmas, and New Year’s? What does coverage look like when a manager is away? Who handles urgent questions, and who is the backup if that person is unavailable?

Then check whether the people who are working can actually perform the responsibilities they are covering. Do they have the training and system access they need? Do they know where to find instructions? Are there deadlines that should move earlier because the usual owner will be away? A schedule full of names is not a coverage plan if no one knows what to do.

Write a short handoff for essential work: what is in progress, what is due next, who owns the next step, and whom to contact if a problem comes up. If an employee has approved time off, respect it. The business should be prepared enough to operate while that person is away.

For a dental office, that might mean assigning phone coverage, patient-message follow-up, insurance eligibility checks, A/R follow-up for claim submissions, and payment posting. For a product business, it might mean assigning inventory checks, packaging, shipping, and returns. The details change; the leadership responsibility is the same.

A good coverage plan also protects employees from spending their entire holiday worrying that the workplace is falling apart without them. If one person is the only person who knows how to complete a recurring task, document the process and train a backup before the next holiday period.

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Do Not Confuse Holiday Sales with Holiday Profit

For some businesses, the holidays bring a significant sales opportunity. The National Retail Federation’s 2026 forecast projects $1.013 trillion in retail sales during November and December, a 4.2% increase over 2025. NRF also reports that holiday retail sales have represented about 19% of annual retail sales over the past five years [3]. That is retail data. It does not mean every business or dental practice will see the same demand.

If you run a retail, e-commerce, hospitality, or other seasonal business, plan for the opportunity without assuming that every sale is profitable. A busy season can still drain cash if pricing, inventory, packaging, transaction fees, advertising, or shipping costs are not part of the calculation.

Here is a simple example. You sell a product for $50 and offer a 20% holiday discount. You collect $40. If the product, packaging, transaction fees, advertising, and shipping cost $32, you have $8 left before general overhead. You made a sale. The next question is whether you made enough money.

Calculate your margin before the promotion starts. Know what each order contributes after its related costs. Set a limit if you need one, and decide what result would make the promotion worth repeating. Do not wait until you have a hundred orders to find out that the discount left too little behind.

If your business is a dental practice or another service business, the same principle applies when you offer a promotion or reduced-price service: understand the direct costs, staffing time, and other requirements before announcing it. Sales volume alone is not a measure of financial success.

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Your Customers Should Know What to Expect

Customers should not have to guess what happens when an employee is on vacation. If you are open and serving customers, make sure someone owns incoming questions and unresolved concerns. If you are closed or working reduced hours, say so in advance and tell people when service will resume.

Clear communication does not mean promising instant responses when you do not have the staff to provide them. It means setting an expectation and meeting it. If shipping will take longer, explain that. If appointments are limited, tell customers what is available. If a service is temporarily unavailable, explain when it will return.

Review unanswered messages, open complaints, customer requests, and promised follow-ups before the holiday schedule begins. Assign a person to anything that cannot wait. Customers may understand that a business has holiday hours; they are less likely to appreciate discovering that nobody knows who is responsible for their issue.

Dental practices have an added reason to plan patient communication carefully. Confirm appointments using the contact method a patient prefers, and give clear information about office hours and response times [5]. Appointment reminders and confirmations can help patients plan, while privacy practices still need to be followed.

In any business, the customer hired the company, not the employee who happens to be away. A reasonable holiday plan lets people take time off while giving customers an honest, reliable way to get help.

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Choose What Must Be Completed by December 31

Look at the remaining working days as they actually are. Thanksgiving, Christmas, school breaks, travel, and employee schedules mean that the last two months of the year are not two uninterrupted months of work. If you plan as though every week will look normal, you may be counting more capacity than you have.

Identify the work that genuinely must be completed by December 31. It might be a financial review, a customer commitment, a claims follow-up process, inventory preparation, next year’s budget, employee training, or a project with a contractual deadline. Put a realistic completion date and an owner beside each item.

Then look at what remains. Some work can wait until January, and that is fine. Give it a January date, an owner, and a first step. A deliberate plan for January is different from work quietly slipping into January because nobody was paying attention.

Do not try to cram twelve months of unfinished projects into the final weeks of the year. The point is to be intentional about what matters, what can wait, and what needs a decision now. If something is not a real year-end priority, give your team permission to stop treating it like an emergency.

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Remember the People Who Helped Build the Business

Year-end planning should not be a list of how much work you can get out of people before they leave for Christmas. Think about the employees who supported customers, handled difficult situations, helped a teammate, and quietly did their jobs well throughout the year.

Have you acknowledged them? Have you told them what their contribution meant? A specific thank-you is more meaningful than a generic note that says, “Thanks for all your hard work.” Mention the action you noticed and why it mattered to the team or the customer.

High expectations and appreciation can exist together. The companies worth building are places where people understand the standards, take pride in their work, and know their contributions matter. A thoughtful plan helps the business finish well and gives employees a chance to enjoy the season they worked hard to reach.

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THE FIVE-QUESTION HOLIDAY BUSINESS READINESS CHECK

Take a few minutes with a pen, your Notes app, or a piece of paper. Answer these five questions honestly. Give yourself one point for each yes.

1. Do you know how much cash your business expects to have available after holiday payroll and expenses?

2. Have you confirmed your holiday staffing schedule and backup coverage?

3. If you are running holiday promotions, do you know what you will actually make after the related costs?

4. Do you have a plan for customers while employees are taking time off?

5. Have you identified what absolutely needs to be completed before December 31?

A score of five means you have a strong starting plan. Keep checking it as the season progresses. Three or four means you have a few gaps to address now. Zero, one, or two means holiday readiness needs to become a priority before the schedule gets tighter.

This score is not a judgment of you or your team. It is a quick way to see whether the responsibilities that matter have an owner and a next step. If you cannot answer one of the questions, write down what information is missing and who will get it.

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A Well-Run Business Can Slow Down Without Falling Behind

I do not believe your only choices are to keep everybody working at full speed through every holiday or to let the business stop functioning until January. You can prepare ahead. You can give employees meaningful time off. You can celebrate with your family and still manage a business that serves customers and handles its money responsibly.

The way you get there is by preparing now. Review your cash, confirm staffing, understand your margins, plan customer coverage, and be realistic about what must be finished before year-end. Then give yourself permission to enjoy the season you worked so hard to reach.

A well-run business should not require you to sacrifice every holiday just to keep it operating. The work you do before the holiday season is what makes the break possible.

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Continue Learning with No Silver Spoons® — Episode 147

This free training prepares you for No Silver Spoons Episode 147, which explores how business owners can prepare for the holidays without allowing the business to fall behind. The episode goes deeper into cash, staffing coverage, promotional margins, customer service, year-end priorities, and the importance of appreciating the people who helped you get here.

Take the five-question Holiday Business Readiness Check into your week. Then listen to Episode 147 with your calendar and numbers in front of you. The goal is not to collect advice. It is to apply it to the business you are responsible for leading.

References

Accountemps. (2018, December 4). Survey finds worker productivity increases during busy holiday season. Robert Half. https://press.roberthalf.com/2018-12-04-Survey-Finds-Worker-Productivity-Increases-During-Busy-Holiday-Season

American Dental Association. (n.d.). Appointment confirmations. https://www.ada.org/resources/practice/practice-management/appointment-confirmations

American Dental Association. (n.d.). Overdue accounts. https://www.ada.org/resources/practice/practice-management/overdue-accounts

National Retail Federation. (2026, October 15). NRF forecasts 2026 holiday sales growth as consumers remain resilient. https://nrf.com/media-center/press-releases/nrf-forecasts-2026-holiday-sales-growth-as-consumers-remain-resilient

Robert Half Technology. (2019, November 20). Survey: 52% of workers will shop online while on the job this holiday season; 44% admit productivity takes a hit. https://press.roberthalf.com/2019-11-20-Survey-52-Of-Workers-Will-Shop-Online-While-On-The-Job-This-Holiday-Season-44-Admit-Productivity-Takes-A-Hit

U.S. Small Business Administration. (n.d.). Manage your business. https://cdn.www.sba.gov/counseling/manage-your-business/

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Disclaimer:

To learn more about Sarah Beth Herman, the author of all free training content you can read her bio here. These materials are intended to provide helpful information to dentists and dental team members. They are in no way a substitute for actual professional advice based on your unique facts and circumstances. This content is not intended or offered, nor should it be taken, as legal or other professional advice. You should always consult with your own professional advisors (e.g. attorney, accountant, or insurance carrier). To the extent, Dentistry Support ®has included links to any third-party website (s), Dentistry Support ® intends no endorsement of their content and implies no affiliation with the organizations that provide their content. Further, Dentistry Support ® makes no representations or warranties about the information provided on those sites. You can view our privacy policy and terms and conditions by clicking those pages in the footer of our website