If you read my book Real Leadership, you might remember that the holiday season is my favorite time of year. Something about those Norman Rockwell paintings that just used to come to life during Thanksgiving and Christmas has stuck with me since then. It’s a time when you can count on the goodness of people; the kind of compassion for the holidays that reminds us why this season matters so much. It’s a time when you can count on the goodness of the human spirit. Or, for those of you who live in the real world, it ought to be that time.
I’m a bit of an idealist, but I also see how the real world operates. I know that the holiday season is one of the most stressful times of the year. The weather doesn’t always cooperate. Flights get delayed. Money is tight. It can be tough with (or without) family around. And this is just the short list of holiday stressors.
But if you are in a leadership position, the holidays are one of the most critical times for you to demonstrate compassion. After all, that is what the season of giving is all about.
Compassion in a leadership context is pretty simple: if it serves someone else, it’s leadership. If it enables someone, that’s just enabling. It’s not about endless opportunities for someone to get it right without consequences. It’s not covering for someone, so no one notices they come in late every single day, lying for someone, or doing their job, so no one finds out they can’t get their work done. All of those things would fall under enabling, too.
Compassion in a leadership context serves people. Especially during such a stressful time of year, compassion lets the team go home early when they have all been working hard, buys pizza to feed the folks who stay late to finish projects, encourages people through giving gifts that serve their unique talents, and divides up and reallocates someone’s work who might be dealing with illness either in their life or in that of their family. Enabling is detrimental, while compassion is beneficial.
While I have touched on a couple of these above, I want to provide you with a list that helps you lead with compassion for the holidays:
Compassion shouldn’t just show up as a seasonal gesture; it should be part of everyday life in your organization. The holidays simply give us a clearer lens to see where our culture shines and where it needs more heart. Embedding compassion for the holidays into your workplace means creating rhythms, policies, and traditions that remind people they’re more than employees; they’re human beings with lives, families, and dreams that matter.
Start by encouraging leaders at every level to model empathy in their daily decisions. Compassionate cultures are built from the top down and reinforced from the bottom up. When team members see their leaders showing genuine care (whether it’s checking in on someone who’s struggling, giving grace for a missed deadline, or sharing a personal moment of gratitude), they begin to mirror that same behavior.
Look for small ways to make compassion a habit, not a headline. Celebrate personal milestones, create opportunities for connection, and remind people that generosity doesn’t end when the holiday lights come down.
The leaders who build cultures of care know this: compassion is contagious. When your organization learns to carry that spirit forward all year long, the holidays become more than a season; they become a reminder of who you truly are.
The holidays are a season of giving, but too often, leaders forget to give themselves the same grace they so freely extend to others. It is easy to get caught up in year-end demands, family expectations, and the pressure to make everything perfect. But even the strongest leaders need to pause and breathe. True compassion for the holidays begins with the compassion you show yourself.
This season is not just about doing more. It is about being still long enough to feel grateful. Take time to reflect on the blessings that came your way this year, even the ones wrapped in challenges. Remember that your worth is not measured by productivity, profits, or performance reviews. It is measured by the love and integrity you bring to the people around you.
If faith is a part of your life, lean into it now. Spend quiet time in prayer or reflection. Ask for peace in your heart, clarity for the year ahead, and forgiveness for the places you fell short. Leaders often carry the weight of responsibility, but they were never meant to carry it alone.
Learn more about how affirmations can help you lean into your faith so you can feel renewed.
When you give yourself permission to rest, to recharge, and to receive grace, you are not stepping away from leadership. You are stepping deeper into it. A leader who leads from a full heart will always have more to give.
The holidays bring out the best and sometimes the busiest in all of us. As a leader, this is your chance to slow down and let compassion take the lead. Remember, compassion for the holidays isn’t just a kind gesture; it’s a mindset that strengthens your team, your culture, and your own sense of purpose.
Lead with heart. Model grace. And when the decorations come down, keep that same spirit of generosity alive in how you lead every day. The best leaders don’t just talk about values, they live them, especially when life feels hectic.
If you want to continue growing as a leader who leads with both courage and compassion, visit my blog to explore more insights, tools, and resources. Let this season remind you: leadership is not about cultivating only perfection; It is about cultivating the best in people.
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“The scarcest resource in the world is not oil, it’s leadership.”
As Co-CEO of the largest independent financal services company in North America, John Addison’s skill as a leader was tested and honed daily. He retired in 2015 after taking the company and it’s people to massive heights. He’s just not done helping people get to the top. Today, he’s at the helm of Addison Leadership Group, INC working daily to mentor and educate new leaders.
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