How to Manage Time-Off Requests During the Holiday Stampede

Practical advice on how managers can make the holiday time-off process fair to employees.
Q:  Every year, everyone seems to want time off for vacation starting around Thanksgiving and going through New Year’s Day. We give off Christmas, New Year’s and half days before both, but I simply can’t shut down my whole business for weeks on end. How can I make the holiday time-off process fair to employees? First come, first served? Seniority? The distance they have to travel to see family?

Trying to accommodate the whole crew’s desires for personal time off can make the holly-jolliest manager start to feel more dyspeptic than Ebenezer Scrooge. I asked for help on this jingle-bell juggling act from Renee Dona, director of human resources for Locations, an independent real estate firm in Honolulu.

At this time of year, it can be challenging to strike a balance between keeping employees happy and maintaining a company’s operational needs, Dona acknowledges. “In my experience, the best and most fair way to manage time off requests is to first establish clear guidelines and procedures for requesting it. Communicating with your staff and planning ahead for holiday coverage minimizes conflict as the holiday season nears.”

She suggests creating a special holiday calendar for November, December and January, to increase visibility for the team. “The next step is to plan your approval process,” says Dona. “I believe the fairest way to manage time-off requests is to take the first-come, first-served approach. This allows employees to plan ahead and submit their requests in advance.”

As requests come in and are approved, add them to the group calendar so everyone can see who is scheduled to be out and which days are still available, as well as what staffing levels need to be maintained and any important project deadlines. “The fact of the matter is that you can’t please everyone. However, with some advance planning and transparency with your staff, you can minimize conflicts and allow ample time to create workable solutions,” she says.

For workers holding down the fort through major holidays, think about ways to make the environment festive – treat the crew to a catered lunch, ensure they have a bit of added flexibility to attend school performances or squeeze in last-minute errands, or host a White Elephant exchange.

We are a small team in retail. Are there aspects of Agile we can try? We keep hearing about it and are feeling left out.

Yes! Agile is a form of project management used by software developers and it can get rather complex – sprint planning, epics, user stories. Still, one idea worth stealing – it’s applicable and can benefit people working in a variety of business settings – is the Daily Scrum.

Though it sounds like an Ohio campus paper, the Daily Scrum is a short meeting (10 to 15 minutes only), held standing up, where each person in the group takes a turn to briefly answer three key questions: “What did you do yesterday?” “What will you do today?” and “Are there any impediments blocking your way?”

There are valuable aspects to this, Agile fans say. One is that all team members are required to chime in – the message is, everyone is important, regardless of their role or title. Two, accountability is built in. Once employees announce what they are about to do that day, they’ve committed and will be held accountable the next day for having actually accomplished that step. Three, any impediments can be quickly addressed by the supervisor – or a project’s “ScrumMaster” – either directly or as an aside after the scrum. Examples of an impediment might be, “I need a partner to work with me on the new product inventory system,” which is an opportunity to pair up an employee with a mentor. Or, “Our painter didn’t return the contract” can become fodder for the first call the manager makes after the scrum.

The Daily Scrum mindset could even be adapted for use by one person, working alone. Write down: What did I accomplish yesterday? What is my goal for today? What would stop me from getting that done? (And what is my plan for moving past that impediment?)

I usually give out gift cards from a local mall to employees, but after the torrential rains on Kauai this spring, and Hurricane Lane and the volcanic eruptions on Hawaii Island, I’m thinking instead about donating the money to charity as a company. What do you think?

Your intentions are noble; I’m worried, though, that some of your employees will have come to expect this gift and will see it as part of their compensation by now rather than as a spontaneous bonus. Will they share in your desire for largesse or feel slighted? As always, it’s often how ideas are communicated. I asked for some input from Eric Laa, senior development officer at the Hawaii Community Foundation, which has helped companies with their charitable giving plans, from employee giving programs to company created scholarship funds to benefit employees. He applauds you for your “compassion and community-mindedness in a year that has been difficult for many in Hawaii.”

“We’ve found that when businesses include their employees in giving, it strengthens their bond to both their company and community,” Laa says. Rather than seeing this as a one-time decision, how about opening up a larger discussion with your team? Some ideas you might consider, he suggests, are “adopting a local charity and suggesting that employees give the gift of time through voluntary service; encouraging employees to give to a cause with a possible dollar match from the company; or inviting an organization to a staff meeting, or better yet, visiting a nonprofit to witness firsthand the great work being accomplished.” There are also resources for learning more ways to support ongoing recovery from natural disasters, statewide, at If I had all the money in the world – and I realize businesses don’t – I’d love to give employees two gift cards: One for themselves and their families, and one where they could provide for families or groups in need.


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