Since I’m now being introduced around the country as “The 5 Rules Guy”, I thought I’d just grab that and go with it for this month’s leadership article!
The Holiday Challenge
For all of us that are grocery retailers, November and December aren’t just regular months. They’re the two biggest sales months of the year, not by a little by a LOT, and it can be overwhelming for our teams and our customers.
Remember one of my top leadership lessons for success:
And for a large number of our customers and team members, it’s emotionally the hardest time of the year.
On one side of the aisle, a grandmother is hunting ingredients for a family favorite recipe. On the other, a young parent juggles a toddler, a phone, and a cart that won’t steer straight. And in the middle — our teams. Team members, managers, and top leaders. People tasked with delivering not just their customers’ favorite foods, but joy, tradition, and stability.
The holiday season tests everything. The pace is relentless. The stakes are high. Yet it’s also the moment we can inspire our teams with our calm demeanor and leave a legacy with our customers that builds momentum going into 2026!
After 48 years in this business, I’ve learned that success this time of the year comes down to five simple holiday rules and just like my 5 Rules for Expected Behaviors – I call these the 5 Rules for Winning the Holidays with Your Team. These aren’t theories — they’re lived out truths over decades of holidays that truly make a difference and can launch us into next year ahead of the competition.
Rule 1: Clarity Over Chaos
The holidays feel like organized chaos. Promotions shift weekly and sometimes daily. Customers demand speed and patience. Teams drown in noise.
Leaders cut through it with clarity and calmness. I’ve always said to my teams this time of the year;
“Just take care of the customer right in front of you and let everything else blur out of your view”!
Clarity doesn’t reduce the work. It reduces confusion. When people know what matters, they can deliver. Confidence follows, and confidence creates calm.
On the front end specifically, cashiers need to take care of the customer they are checking out, but it’s also good to just make eye contact with the ones in line and let them know – “we’ll be right with you” – just recognize them. That’s enough. Just don’t ignore them.
How to practice it: Start every shift with a short huddle. Remind them to “be the calm” for our customers – and take care of them one at a time. Keep it simple. During the surge, a clear leader is a steady leader.
Rule 2: Lead from the Floor
Leadership loses credibility when it hides in the office. The holidays especially demand visibility.
On the weeks of Thanksgiving and Christmas, we always emptied out the support office to get out in stores and lend a hand. You simply can’t have enough people on the payroll in each store to take care of the big surge in business during these two months. This is something I always enjoyed and was a great reminder for me on how hard our teams in the stores work. This also really lifts the moral of the teams to see that “everyone” is out in stores helping!
Proximity builds trust. When leaders stock shelves, carry bags, or walk the aisles helping customers, they model what they expect. They remind everyone that no task is beneath them.
Bottom line: During the surge, the best clipboard is a shopping cart. The best office is the floor. And the best leadership is active and present.
Rule 3: Protect the Team’s Energy
The hidden enemy of the holidays isn’t inventory or logistics. It’s exhaustion.
It’s easy this time of the year, to be so busy, we tend to cut the breaks out or shorten them and that’s a giant mistake. Our teams are human, and everyone needs their full breaks and it’s our job to plan ahead and if we do, there is no reason our teams don’t get their breaks.
Leaders must guard energy. Not just physical, but emotional. When people are treated like machines, burnout follows. When they’re treated like humans — given encouragement, rest, and recognition — they will give more than you can imagine.
Practical moves: Rotate and share heavy tasks too. Have cold water and snacks for the teams. Acknowledge the grind. Sometimes a leader’s words, written or spoken — “I know this is hard, and I appreciate you” — are more powerful than a bonus. Everyone simply wants to be appreciated!
Great leaders are energy protectors. Energy is the fuel that keeps chaos from winning.
Rule 4: Double Down on the Customer Experience
Holidays amplify emotions. A missing spice can feel like a crisis, and this leads to getting ahead of the purchasing of key holiday items. Good store directors anticipate that there are normally a higher number of manufacturers outs this time of the year, so get key items in early.
A kind word can feel like a gift. (Remember Rule #2 from my book – BE KIND!)
When a customer asks for something – we need to walk them over to it to help them find it. We’ve always had a rule of “NEVER POINT” where something is – show them where it is – and take a few minutes to help with anything else on their list.
We’ve all seen this quote from Maya Angelo, it’s in my book – and it’s particularly valuable during this holiday time of the year and we can give our customers the best service in town and trust me, they’ll remember how we made them feel!
This is also the best time of the year to let your humor loose. Nothing relaxes our teams and our customers more than a good joke or just a big smile, and it’s ok to use ourselves to joke about.
How to lead it: Train teams to slow down with customers, even when the pace says hurry. Empower them to fix problems without waiting for approval. And above all, model patience and kindness yourself.
Holiday shopping isn’t just about groceries. It’s about family traditions and memories. If you serve people with dignity, you’ll win loyalty for years.
Rule 5: Celebrate the Wins
During the rush, days blur together. Teams finish shifts exhausted, wondering if anyone noticed. That’s why celebration is essential.
I’ll never forget walking into one of our stores after a record-breaking day. The store director had partnered with a vendor to feed the teams the next day. As tired as everyone was – there was laughter and comradery happening that money just can’t buy! These moments turn fatigue into pride.
Celebration doesn’t have to be big. A “holiday hero” shout-out. A team photo on the wall. Allowing a departure from normal dress codes into holiday dress and even sports days on the weekends help a ton to relax our teams. It’s about recognition, not expense.
Leadership truth: When you celebrate, you transform pressure into purpose. You tell people: we’re not just surviving — we’re winning, together.
Legacy for the Holiday Season
When January arrives, what remains isn’t just the sales report. It’s how leaders made people feel. And trust me, I’ve seen many a failure during this time and have learned the hard way on how to use these five rules of winning the holidays!
Associates remember the night their manager covered a shift. The snacks after a long day. The season when leadership stood shoulder-to-shoulder with them. Customers remember patience, kindness, and care.
The holidays are remembered. They become stories told years later. And they define leadership legacies. (These five holiday rules can also be used for Grand Openings and Hurricane/Weather related sales as those are times to gain momentum by being different.)
So as the surge approaches, live the 5 Rules:
- Provide clarity.
- Be present.
- Protect energy.
- Elevate the customer experience.
- Celebrate the wins.
Do that, and you won’t just guide your team through the season. You’ll inspire them into the new year and beyond.
“Leadership is not about getting through the season. It’s about making the season matter.”
