It seems each year the season starts earlier, the events grow bigger, and the expectation to be “festive” ramps up long before most of us have even found the box of decorations in the attic.
For many of us, late November marks the beginning of a complicated stretch. A blend of anticipation, pressure, nostalgia, grief, excitement and exhaustion that defies the neat, glittery image we tend to project onto this time of year.
Today, I want to explore how leaders and teams can communicate with more awareness and sensitivity especially when the social calendar fills up faster than the emotional energy needed to navigate it.
Because not everyone is ready for cheer on command.
The Assumption We Get Wrong
Workplaces often behave as if this season is universally uplifting. But in every office, right now, there will be:
It’s always a mix.
And when organisations push a “get into the spirit!” message without considering that diversity of experience, it can feel less like inclusion and more like pressure.
Leaders rarely intend this. But intentions don’t insulate people from impact.
Leaders Communicate in Social Spaces – Whether They Mean To or Not
One of the most overlooked leadership moments is the office holiday gathering. Because it’s social, many leaders mentally categorise it as “off-duty”. But colleagues don’t stop reading leadership cues just because there’s a canapé in their hand.
The following tiny moments reveal more about leadership than a dozen strategic memos:
And for someone who is already feeling fragile or cautious, these signals carry weight.
Guardrail One: Invitations Should Feel Like Invitations Not Obligations
A surprising number of organisations still send holiday event messages with phrases like “attendance expected” or “full participation encouraged”.
People don’t relax when they sense expectation wrapped in tinsel.
A simple shift makes a world of difference:
“You’re warmly invited.” “We’d love to see you if you can make it.”
Guardrail Two: Create Options Not Just Events
Holiday celebrations don’t have to be built solely around large, noisy groups. Consider offering:
Flexibility is a form of respect.
Guardrail Three: Not Everyone Needs Fixing
People who stand along the edge of the room or step outside for air aren’t “problems to solve”. They’re colleagues managing their own internal weather.
A gentle check-in – “How are you finding things?” – is enough. No prying, no nudging, just connection.
Often the most meaningful leadership move is simply acknowledging someone without making them the centre of attention.
Guardrail Four: Say the Quiet Thing Out Loud
Many leaders fear mentioning the emotional complexity of this season in case it dampens the mood. It rarely does. In fact, it often has the opposite effect.
A short, sincere acknowledgement can set the tone beautifully:
“This time of year is joyful for many and challenging for others. However you’re arriving today, you’re welcome.”
It opens the room. It softens the edges. It makes space.
Employees Have Responsibilities Too
Leaders are not the only ones who shape culture. Colleagues can help by:
End-of-year pressures can bring out the best or the worst in teams. It depends on how intentional we are with one another.
Authenticity isn’t about over-enthusiasm. It’s about truthfulness.
And connection isn’t about volume. It’s about presence.
The real opportunity this year is not to throw the “best party”, it’s to cultivate spaces where people feel seen, included and safe to show up fully, even on the days when they’re struggling.
And that, as ever, is the essence of leadership at the holidays – and every day.
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