The Santa Challenge: Why Thoughtful, Kick-Ass Gifts Make You a Better Leader
What if one of the most powerful leadership and communication skills you could develop had nothing to do with presentations, emails, or meetings — and everything to do with the gifts you give? Welcome to the Santa Challenge: a deceptively simple idea that can transform how the people around you experience your leadership, your friendship, and your attention.
A T-Shirt Shop That Smells Like a Bakery
To understand where this idea comes from, you need to meet Johnny Cupcakes. His real name is Johnny Earl, but everyone knows him as Johnny Cupcakes — and his business is unlike anything you've ever seen. Walk into one of his stores and you'll swear you've entered a cupcake bakery. The air is thick with the scent of vanilla frosting. There are fridges and ovens lining the walls. But open one up and you won't find pastries — you'll find t-shirts. Buy one, and it comes wrapped in a pastry box.
Every single customer, whether they purchase something or not, leaves Johnny's store with a story they can't wait to tell someone else. Johnny is a master of what he calls "brand hysteria," and he brought that energy as a keynote speaker at the Activate Conference. But it was during an interview on the RE/MAX Hustle podcast that he shared a story that changed my perspective on leadership entirely.
The Best Christmas Gift You Ever Received
One day in July, a few years back, Johnny gathered his staff in the boardroom for what seemed like a casual conversation. He asked everyone a simple question: What was the best Christmas gift you ever received as a child?
Think about that for a moment. What was yours?
One by one, his team members shared their answers. They recalled rare toys, cherished surprises, and long-forgotten moments of pure childhood joy. Smiles spread across the room. Nostalgia filled the air. It was a fun, lighthearted conversation — or so everyone thought.
What the team didn't realize was that their leader was taking notes.
Six Months of Quiet, Intentional Effort
Over the next six months, Johnny quietly went to work. He scoured eBay, Amazon, and garage sales, hunting down every single one of those gifts — the rare toys, the nostalgic treasures his employees had described with such fondness. Then, at Christmas that year, he gave each staff member their favorite childhood gift.
Some of them cried.
It wasn't about the monetary value of a toy. It was about knowing their leader had listened. He had remembered. And he had cared enough to act on it. That single gesture communicated more than any corporate memo or team meeting ever could.
What This Tells Us About Communication and Leadership
Consider this statistic: 91% of employees say their leaders lack communication skills. That's a staggering number. Now ask yourself — on that Christmas morning, how many of Johnny's employees would have said he lacked communication skills?
My guess is zero.
Johnny demonstrated that impactful communication isn't always about what you say. Sometimes it's about what you do with what you've heard. Listening — truly listening — and then acting on it is one of the most powerful forms of communication a leader can practice.
A Candle That Smells Like a Record Store
Johnny's story inspired me so much that I decided to put his philosophy into practice — with him. During our interview, he had mentioned one of his favorite things in life: the smell of a record store. It traced back to his days working at Newberry Comics in Boston. He said the scent of vinyl and album sleeves simply brought him joy.
So I scoured the internet for a candle that smelled like a record store. As far as I could tell, there was exactly one shop — a small store in Los Angeles — that sold a vinyl-store-scented candle. I ordered it, paired it with a handwritten note thanking him for being on the podcast, and sent it his way.
It was a small gesture. But it was intentional, personal, and rooted in something he had shared with me — because I had been paying attention.
The Santa Challenge: Your Turn
Here's the challenge I want to leave you with:
- Give at least five next-level, kick-ass gifts this year to people who mean a lot to you.
- These don't have to be expensive — they have to be thoughtful.
- They don't have to happen at Christmas. In fact, it's even better if they don't. A random, unexpected gesture of appreciation can be far more powerful than a holiday obligation.
- Pay attention to what people say they love, miss, or value — and then act on it.
The Santa Challenge isn't really about gift-giving. It's about showing people — your team, your friends, your family — that you were listening all along. In a world where 91% of employees feel unheard by their leaders, the simple act of remembering what someone told you and doing something meaningful with that information can set you apart. Be the kind of person who pays attention. Be the kind of leader who acts on it. That's impactful communication at its finest — and it doesn't require a stage, a microphone, or a single PowerPoint slide. Just open ears, a generous heart, and the willingness to follow through.