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Work-Life Balance

How to Manage Your Team's Calendar During the Holidays

Ample time off at the holidays is good for morale and manageable with planning.
How to Manage Your Team's Calendar During the Holidays
Image credit: shapecharge | Getty Images
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Entrepreneur and Connector
5 min read
Opinions expressed by Entrepreneur contributors are their own.

The end of the last quarter is a time of rest for many, but founders and their teams keep working hard to set up their companies for success in the new year. Just because the grind never stops, however, does not mean that founders should take their teams for granted. But there are ways to manage your team's calendar during the holidays.

My companies are closing for 10 full days during the holiday season. I want our employees to know that we recognize their value and respect them enough to provide a manageable work-life balance.

We aren’t closing shop for 10 days without proper preparation, of course. Until those 10 days arrive, our teams from top to bottom are working tirelessly to ensure that we won’t leave anything unfinished. Our break will be much more enjoyable with the knowledge that we did everything necessary before closing shop for the season.

Managing a team’s calendar during the holidays is a delicate task. Some people want to work more in a quiet office, while others want to take long breaks. The key to managing a holiday calendar is to treat employees with respect without compromising on the company’s goals in the bargain.

Related: The Best Founders Are Already Planning How to Thank Their People During the Holiday Season

Follow these scheduling tips to manage a team through the turmoil of the holiday season:

1. Understand what they want.

Rather than announce the office will close for two weeks without discussing it with anyone, talk to people about what they would like to do for the holidays. Some teams would prefer to grind it out for a few weeks to earn a long break, like we’re doing, but others would rather take it slow. Keep in mind that not all employees celebrate the same holidays.

Employees respond better to leaders who involve them in the decision-making process. Involve them, but don’t let them run the show on their own. Paula Santonocito of Recruiting Daily Advisor argues that, while employee involvement can provide a sense of value and ownership to employees, it can also lead to decision paralysis within the organization.

Find the balance by soliciting employee input then making the call that’s best for the company. Maybe that means going with what the majority wants. Maybe it means allowing people to opt-in to an alternative holiday schedule. Whatever the decision, don’t let one group saddle another with extra responsibilities.

Related: 6 Ways to Keep Employees Engaged During the Holiday Season

2. Lean on freelancers to fill the gaps.

Freelancers are always available to help small companies meet goals when internal employees don’t have the capacity. This is especially true during the holidays when entire teams can disappear for days at a time.

Reach out to trusted freelancers early in the month to ask about their capacity. If they have some room on their schedules, talk to teams about their holiday plans to coordinate projects. Keep track of this in a calendar app so that you don't forget. We get so busy these days that we often don't message till it's too late.

Of course you don't rely on freelancers to do jobs that would be better handled internally. You can take this opportunity to tackle some projects that might not come up during the rest of the year. Work with contractors to come up with creative pieces of content. Trust freelancers with big tasks to learn which ones are dependable, then give them more work during the coming year.

Don’t worry about the potential cost of a freelancer/full-timer mix. Michael Solomon, co-founder of 10x Management, broke down the budget on Huffington Post and found that mixing freelance with full-time is the most cost-efficient management method.

Related: 7 Ways to Manage Employee Holiday Time Off

3. Relax work-from-home policies.

Remote workers are typically more productive than their in-office counterparts, as Harvard Business Review discussed back in 2014. Now that telecommuting tools have gotten even better, that productivity gap is even wider. That goes double for the holidays when office workers take every opportunity to talk about gift recommendations and football.

Encourage employees to work from home whenever necessary during the holiday season. If the company has a rule about needing an excuse, drop that rule (permanently if possible, but definitely for December). When parents don’t have to worry about their kids’ school schedules and travelers are free to work from the road, companies reap the benefits of anytime, anywhere productivity. It also cuts down on all of the extra office-holiday-chatter that is a huge time-suck.

Maintain a semblance of order by clearly communicating expectations and reminding employees of work-from-home guidelines. People still need to attend important meetings and meet productivity goals at the end of the year. Treat people with respect and assume they want to do good work. If the team is a good one, it will reward that faith many times over.

The holidays are almost here, so don’t delay. Work with teams to create a schedule (scheduling beats hustling) that works for everyone, set expectations and treat employees with the respect they deserve. When the holidays end, return to work refreshed and ready to tackle the new year.

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