In this episode of Veteran Led, John Berry shares practical advice for leading your team during the holiday season. From bonuses and holiday parties to showing genuine appreciation, John explains how great leadership sets the stage for success in the new year.​
The best holiday leadership isn’t about extravagant gifts or mandatory fun—it’s about understanding your team, showing genuine appreciation, and setting the stage for success in the new year.​
Welcome fellow veterans. From the tip of the spear to in the rear with the gear, I went from active-duty Infantry to reserve-component logistician. I’m your host, CEO, entrepreneur, trial lawyer, and Lieutenant Colonel Retired, John Berry.
What does great leadership look like during the holidays? Now, many of us are familiar with the holiday bonus, right? That’s the bonus that’s paid out at At the end of the year, it’s usually a gift amount. It’s not really an earned bonus, but this is just something a little extra for the staff, for the team. Now, I have a friend that runs a phenomenal company, and he doesn’t believe in that. He says, Look, my team gets what they earn. Our culture is such that we don’t give out extra money during the holidays. In fact, we have specific metrics, and if our team members hit those metrics, they get the bonuses, and we don’t do anything in addition to that. His team likes it. It works for him. I know other leaders who say, Oh, no, the holidays are extremely important to our team. We make sure that the holiday bonus goes out before Thanksgiving so that our team members can spend that money on Black Friday and start buying presents immediately.
Now, I know some people that also have extravagant Christmas parties where they rent out an amazing space and there’s bands and dancing and the same mandatory fun you would expect to see it a military ball.
I know other organizations that do absolutely nothing. Instead, they say, No, we’d rather give our team member the time off. Instead of spending a ridiculous amount of money on a holiday party, we are simply going to give our team members more time off during the holidays. We’re going to give them that entire week from Christmas to New Year’s. There’s no right answer here. I’ve seen some organizations where they say, Well, we have our executives go do something else, and then for the rank and file, we have a separate party for them. We don’t really like to mix. This is equivalent to the officer NCO type Christmas parties. You probably remember when there was the Officer’s Club and the Enlisted Rank’s Club, and it created a separation that I think in most companies we try to avoid, we want everybody to feel like they’re part of a team, and that if we’re working as a team, it doesn’t matter whether you’re an officer or you’re an enlisted soldier, we work together to accomplish the mission. We try not to have fraternization. We also try to let people know that their value exceeds the rank that they hold in the company.
How do you measure whether you are a good leader during the holidays? Well, I think it all comes down to results, not just your year-end results and how excited people get to accomplish those year-end goals because they know they’re going to have some time to decompress, or maybe how they start the new year. Do they start refreshed? Do they start fired up? Do they love having that blank slate of the new year? Have you set the conditions for success in the future? I think that’s what great leadership looks like, being able to end the year positively with a showcase of the accomplishments, but then being able to start the new year with momentum and excitement. And that is the leadership that’s necessary during the holidays. So does that mean people need more time off? Maybe, or maybe they don’t. But the key is that you, as the leader, set the conditions for success, and you have to know your team. It’s one thing to know yourself and know what you want for the holidays, but you have to know your team, know what your team wants to do for the holidays and ask. A lot of our best parties during the holidays were not designed or planned by the leadership team.
In fact, some of the worst parties were designed by the leadership team. Why? Your leadership team may be out of touch with the majority of your employees, especially when you get those senior leaders that have been around a while. Instead of having a great DJ, they want to have a string quartet or a jazz band. That doesn’t mean that string quartets or jazz bands are bad, but maybe most of your employees, depending on their age, might not be into that stuff. The key is to make it about them, not about you. We all have suffered through mandatory fun in the military. We’ve gone to stuff that was just horrific, and it was all about the leaders, and it wasn’t about the team. If you’re going to have a party, make it a party. Make it about the team. Don’t make it about you. Don’t make it about the senior executives. Make it about the team as a whole, and find the people who can make that happen. What I found is if you get junior team members involved in the planning, in the decision making, not only does it make the party a lot more fun, but now you have started something in your culture where the junior team members feel comfortable participating in the decision making in the organization.
It’s a great place to start because, let’s face it, if you screw up a holiday party, it’s not the end of the world. There are going to be the senior executives that will ensure that you do your draw, your risk assessment worksheet to ensure that nobody does anything really stupid. But allowing those junior team members to participate in designing, planning, and executing something that is fun for the entire organization gets them interested in leading. Gets them interested in doing the things that we do on a daily basis. The difference is they often don’t get the opportunity because they’re just seen as junior team members. But when you have those holiday parties, it is a great opportunity to let someone else take charge of the organization.
In conclusion, look, there is no right way to lead during the holidays. You want to give no bonuses that might be okay in your organization. You want to give bonuses prior to Black Friday so that people can buy presents early, great. You want to give bonuses based on a whim? Maybe that works in your organization. But ultimately, it’s about what the team expects and the culture that you want to set.
Now, one great opportunity during the holiday season is if you have a holiday party, let those junior team members get involved. Let them get involved in the planning and the execution once they have a taste of leadership. And this is a non-expensive taste of leadership because they can’t really mess it up. It’s a great opportunity for them to learn whether they like leadership and whether they have the ability to influence their peers. So great leadership during holidays doesn’t look like a perfect party. What it looks like is giving the team a chance to have fun and giving other team members the chance to lead. And don’t give out a water bottle every single year, especially not the logoed merchandise every single year. People don’t want your logoed merchandise. They may like it. They may like to wear your swag, but they don’t want it as a gift. In fact, some of the most impactful gifts I’ve received from team members and vendors had no logos on them whatsoever. I can think of one vendor that my wife and I got married. It was during COVID. We didn’t invite a lot of people, and we said no gifts.
And this vendor sent us these white Cutco knives that matched our kitchen. And they’re in our kitchen every single day we use those knives, and I think about that vendor. Now, that was a great gift. Did it have the vendor’s logo on it? No, but it was a gift. It was something we needed. When you think about holiday, if you’re going to do holiday gifts for your staff, don’t give them logoed merchandise. I mean, give them logoed merchandise throughout the year. Have cool swag. I’m not saying don’t have swag and not have your logo all over everything. But when you’re giving a gift, make it a gift. Don’t make it about you or your company. Show genuine appreciation. One way we used to do that is we used to find an opportunity every week to celebrate a team member that did something extraordinary, and the gift would be something very personal to that person, whether it was a soccer jersey or a yoga mat, but it had to do with that person. That went well for a while. When that started to fizzle, we found that there were special occasions. We had one team member that when the 49ers went to the Super Bowl, this person was a huge 49ers fan.
We got that person, their favorite 49ers jersey. It’s things like that that you can do in gift giving that make a difference. But in the end, the gift is always about them. Don’t think about what you would want. Think about what that team member would want. How do you know? Ask. Sometimes it’s worth doing things like celebration surveys or other ways to find out how your team members want to be celebrated, what are the gifts you could give them. You don’t just have to give the gifts during holidays. But I want to say that all of this is mostly not that important. At the end of the day, people come to your team because of the culture, the mission, and the opportunity for a bigger future. It really doesn’t matter whether you give them gifts or not. If you’re a great organization, they’re going to stay on the team and they’re going to make your team successful. However, showing appreciation from time to time with gifts can make a difference, especially for a team member that’s going through a rough time. You get that opportunity to be a hero to them. I found that some of the gifts that were most impactful were not the awards that someone received when they felt like they were on the top of the world for winning.
But the gifts that I gave when that person was having a bad day or a bad month and saying, Hey, we believe in you. Sorry, things are not going well. We know things will turn around for you because you will turn them around. And giving them a gift at that point to say, Look, we celebrate you even when you don’t win because we expect you to win in the future because you’ve won in the past, that can make all the difference.
Thank you for joining us today on Veteran Led, where we pursue our mission of promoting veteran leadership in business, strengthening the veteran community, and getting veterans all of the benefits that they earned. If you know a leader who should be on the Veteran Led podcast, report to our online community by searching @veteranled on your favorite social channels and posting in the comments. We want to hear how your military challenges prepared you to lead your industry or community, and we will let the world know. And of course, hit subscribe and join me next time on Veteran Led.
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