The Art of Holiday Leadership: A Manager's Guide to December
Because managing people means managing their traditions and time off too.
There's something about December that makes time feel both stretched and compressed. In global teams, this stretching takes on additional dimensions - across time zones, cultures, and celebrations that mark the calendar in distinct ways.
The end of the year brings a particular set of challenges for managers. These matter the most:
Plan Around Cultural Rhythms
Managing a team across Singapore, Stockholm, and San Francisco meant juggling multiple holiday calendars. My European team members typically took extended breaks from mid-December through early January - it's simply part of their work culture. U.S. colleagues expected the week between Christmas and New Year's to be light or were off work, while APAC team members planned around entirely different celebrations - from Lunar New Year to Diwali. Missing these patterns leads to frustrated team members.
Set Clear End-of-Year Boundaries
If you're still scheduling performance reviews for mid-December, stop. Just stop. Getting meaningful input becomes nearly impossible when half your stakeholders are mentally (or literally) already on vacation. Wrap up major evaluations by early December at the latest. My teams aimed to gather all feedback by November 15, with December 1st as the hard deadline for submitting all evaluations. This timing lets everyone start their holidays without lingering tasks.
Respect the Recovery Runway
January isn't just about new beginnings - it's about gentle re-entry. Expecting peak productivity in the first two weeks of the year is like asking someone to run a marathon right after waking up. We found that scheduling the first week of the year for team alignment and planning, with major deliverables starting in week three, worked best.
Organize Fair Coverage
This one's tricky, but crucial. My teams included members from cultures where month-long winter breaks are the norm working alongside others who get just 15 precious vacation days annually. Therefore, we created a fair rotation system and communicated expectations early so no one felt like they're always the one holding down the fort. Our solution was threefold:
A shared calendar marked three months out with all cultural holidays and breaks.
Clear handoff protocols between time zones with all teams adhering to a simple triage system:
Critical issues = response needed within 2 hours (clearly defined: Sev 0 and Sev 1s such as production down, data breach, customer-facing outages)
Important issues = response by next business day (Sev 2 issues such as system degradation, non-critical bugs)
Everything else waits until return.
Rotating coverage teams - Team members would self-select and rotate coverage of major holiday periods annually - those who covered Christmas one year (for example) would get priority for for their preferred holiday next time.
Navigate Celebrations Thoughtfully
Gift-giving across cultures requires extra thoughtfulness. Skip the professional development books - what feels like inspiration to the manager lands as obligation to recipients. Nothing dampens holiday joy quite like an implied reading assignment that turns into a January homework check-in.
Where a bottle of wine might be a thoughtful gift in France, it’s inappropriate for team members who don't drink alcohol. I once received a gift basket containing cured meat that I couldn’t eat as a vegetarian. Cash or cash equivalents, perfectly normal in some Asian cultures, could violate company policies.
Instead, we found success with:
Team donations to food banks chosen by the team.
Personal appreciation notes highlighting specific contributions.
A holiday fund ($50 per person) that each team member directs to their chosen charity.
Some of our best moments came from organic sharing of traditions. During one virtual celebration, a colleague from Sweden shared pictures of her St. Lucia Day celebration, including the saffron buns she bakes every December 13th. Another team member shared his special Diwali dessert recipe, also featuring saffron, leading to an engaging discussion about festival foods across cultures. These natural conversations built stronger connections than any scheduled team-building exercise.
The most successful holiday seasons I've managed weren't about perfect planning, but about setting clear boundaries and honoring different approaches to celebration and rest. One of our highest-performing quarters followed a December where we deliberately slowed down, let people fully disconnect during their time off, and focused on starting January fresh.