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Leadership Over the Holidays

The holiday season is upon us once again! My days have been filled with social events, shopping, and planning for my family to gather together... but I’m mindful of the fact that this time of year brings a wide range of joys and challenges to everyone, and not everyone handles them the same. I captured my thoughts on leading an organization through the holidays in the attached blog. I hope you find it useful.


I’ve always enjoyed the holidays. Whether we were celebrating Easter, the 4th of July, Thanksgiving or Christmas my family and I always had a wonderful time. The ability to gather with friends and family, enjoy good food, and share in the joys of the moment were experiences I treasured from childhood through adulthood. The warm feelings laid an emotional foundation that led to gleeful anticipation of the next holiday…it couldn’t come fast enough!

As I became a leader in the Air Force I brought that same enthusiasm to whatever unit I was leading. My wife and kids joined in the preparation for the event – helping to decorate the building and workspaces, making food to share with the members of the outfit, and participating in the entertainment – be that gift exchanges or picnic games. It was always fun for us, but it didn’t take me long to understand that not everyone felt the way we did…for a variety of reasons.

First; not everyone is happy during the holidays. For some, holidays bring extra stress; the “pressures” of participating in social engagements are not something everyone delights in. Forcing members of the unit to participate in external/non-work related activities is not a path that leads to high morale. I remember when I was a young officer – the Wing Commander had a mandatory New Year’s Day reception. All Officers were expected to be there – in our Mess Dress (a military tuxedo) and go through a receiving line so the Wing Commander could say “Happy New Year”. I can’t think of a single member of my unit that thought: “This is great! I’m so glad the Boss made me do this.” Instead, we stood around for the minimum required time and grumbled. I’m certain the Wing Commander didn’t have that in mind when he scheduled the event; he undoubtedly viewed it as a traditional way of greeting his command – something he’d experienced as a young officer and continued. If he’d understood that the members of his organization had a different take on that tradition maybe he’d have looked for an alternative way to accomplish the same thing…letting his unit know he sincerely wished us well in the upcoming year.

Second; some might find the holidays particularly challenging because of a significant emotional event…the physical separation of a loved one who’s away from home; the death of a family member or friend and the pain experienced in going through the holidays without them. For those members, a holiday gathering is a painful reminder of the absence of people who’ve always made the holidays more special. In those cases, there’s little that can ease the hurt – though a compassionate understanding of their situation can help minimize unintended harmful actions/comments.

Here are some thoughts on leading your organization through the holidays:

  1. Know your people well enough to have an understanding of what’s happening in their lives. I acknowledge that’s tough to do if you lead a very large organization, but you can focus on those under your immediate supervision – and let them know that you expect them to do the same for those working at levels below them. When your workforce understands that the Boss has an awareness of the challenges of their life outside the workplace they’ll feel respected, appreciated and cared about…all of which leads to greater productivity.

  2. Not everyone celebrates the same; make accommodations in your celebration for differing faiths and backgrounds. Holding “mandatory” (stated or unstated) celebrations should be carefully thought out before you issue an edict. Not everyone celebrates the 4th of July or Thanksgiving – uniquely American holidays. Likewise, some of your workforce might celebrate different cultural holidays that go completely unrecognized by most. Be ready to “referee” challenges to the status quo and be open to change. I think that’s what an effective leader does; shepherd the organization through changes and help them emerge a cohesive, committed team.

  3. Dedicate time to personally engage with your folks; this is always a good thing to do – it’s even better to do it during the holidays. I used to volunteer to serve lunch at the Dining Facility on Thanksgiving and Christmas Day…almost every Commander, Chief Master Sergeant, and First Sergeant did. Some might think that breaking away from my family celebration was a tough decision but it wasn’t. Over the years I found those moments to be among my best memories. The casual conversations with Airmen as I piled food on a plate were wonderful – as were the longer talks I could engage in after my “shift” was over. I learned who they were, where they were from, what they did, and just generally listened. Occasionally I learned about problems that I could address; though that was not the intent of the conversation, it certainly was a side benefit and hopefully was valued by the Airmen as it was by me. Talk to your people. It sounds simple, but it was always gratifying (and revealing) to see how much they appreciated the Boss spending time with them.

As I write this, it’s two weeks until Christmas. My house is beautifully decorated, inside and out, and my wife and I are excited about our children and grandchildren being with us for a short time. I know we’ll have a full house with lots of conversations, music, and excitement. I also know that there are military members in the US and around the world who will not share Christmas with their loved ones. Your organization – military or otherwise – has the same challenge. I know what the military leadership is doing to try to make the holidays enjoyable. I hope you’re doing the same for your folks. Leading them through the holiday season is tough…but can be done well as long as you put some thought into it.


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