Navigating the Holiday Season: Lessons from 20 Years in Operations Leadership

After two decades in operations leadership, I’ve learned a lot about what not to do during the holiday season. I’ve been guilty of waiting too long to approve PTO, making last-minute schedule changes, and even sharing my holiday joy on social media while my team was overwhelmed. These missteps didn’t make me a bad leader—just an inexperienced one. Over the years, I’ve developed strategies to keep teams engaged and supported during the holidays, even when the lights and sparkly things pull their attention elsewhere.

Here are my best tips for navigating the holiday season as a leader. If you haven’t already started thinking about the time off, let’s start now!

1. Clear Communication

Announce Office Closures and Schedule Changes Early

Let your team know about office closures and schedule changes as early as possible. Use multiple channels—email, team meetings, and even your company’s social media—to spread the word. The earlier you communicate, the better prepared your team will be.

Designate Emergency Contacts

Assign someone to handle emergencies during the holidays, and ensure everyone knows who this person is and how to reach them. Compensate them fairly for their availability through extra pay or additional time off. This ensures that your team feels supported, even when you’re not available.

“Early in my career, I was asked to work Thanksgiving, Christmas Eve, Christmas Day, and New Year’s Eve. I did it happily, but it wore on me. I was thanked, sure, but it felt more like a ‘thanks for doing your job’ than genuine gratitude. I wish someone had really acknowledged my effort—maybe said my name in a meeting or given me an extra day off. That experience shaped how I approach leadership today. When my time came as a senior leader, I made sure to do things differently.”

2. Planning and Scheduling

Approve PTO Requests Promptly

Don’t delay in approving PTO requests. Your team needs time to plan their holidays, and timely approvals show that you respect their personal lives.

Create Schedules Early

Get work schedules finalized and shared as soon as possible. This ensures proper coverage and allows your team to coordinate their time off effectively.

Plan for the Unexpected

Someone will inevitably get stuck in an airport, fall ill, or face an emergency on a critical day. Build flexibility into your schedule by assigning an extra person during key shifts. This not only provides a safety net but also reduces stress for everyone.

“Leading a team of 50, I learned this lesson the hard way. One Christmas morning, we were the only business open in the area, and the first person scheduled to arrive didn’t show up due to an emergency. We started the day on a stressful note. After that, I began scheduling extra hands during key transitions—opening, mid-shift, and closing. It created flexibility, shorter shifts for those who wanted them, and opportunities for others to stay longer if they chose. Most importantly, it gave us peace of mind knowing we had safeguards in place.”

3. Support and Flexibility

Show Up for Your Team

If your team is working on major holidays like Christmas, be there for them. Cover their breaks, bring homemade treats, and, most importantly, thank them for their dedication. If you can’t be there in person, empower your second-in-command to step up and show support.

Encourage Work-Life Balance

Give your team a little breathing room during the holiday rush. Allow them to take an extended lunch to run last-minute errands, pick up packages, or get a holiday haircut. Small gestures like this can make a big difference.

“I once worked under a leader who kept score of every hour. Every minute was accounted for in the name of fairness, but it didn’t feel fair. When I needed to pick up my mother from the airport at midday, I knew what was coming: ‘I know you’ll make the time up.’ And I did. But what I really wanted to hear was, ‘I know you put in more time than you bill me for.’ That small acknowledgment would have meant the world.”

Offer Flexible Work Arrangements

Consider remote work or adjusted hours to accommodate your team’s holiday plans. Flexibility shows that you trust your team and value their well-being, which goes a long way in building loyalty and morale.

4. Reflect and Improve

Review and Reflect

After the holidays, take time to review how things went. Gather feedback from your team and use it to improve your planning for next year. What worked? What didn’t? This reflection will help you refine your approach and build a stronger, more resilient team.

Consistent Planning Matters

How you handle the holidays reflects your overall planning skills. Use this time to demonstrate that you’re organized, thoughtful, and committed to your team’s success.

“A few years ago, a client closed their business for three weeks over the holidays. When they returned, they found water damage from a burst pipe. No one knew when it had happened, but the equipment was fried, the stock was ruined, and they had to remain closed for another three weeks to repair and rebuild. Now, they pay an employee to check on the space daily during closures. It’s a small investment that prevents major disasters.”

Remember, great leadership during the holidays isn’t just about getting through the season—it’s about building trust, loyalty, and a culture of care that lasts all year long. Here’s to leading with intention and making this holiday season your team’s best yet!