What’s this? How Jack asked the wrong question.

Natalia Monnard
7 min readDec 30, 2020


The Nightmare Before Christmas: A Leadership Lesson

I remember falling in love with Jack Skellington as if it was yesterday — except it isn’t. The Pumpkin King first stole my heart in 1993 when Tim Burton brought his magic to the big screen in what would become a major cult movie: The Nightmare Before Christmas. It has become an all-time favorite for many people around the globe, not only because it is a technical and musical masterpiece, but because it is an emotional one as well.

Since I first saw it at the age of ten, watching it around the holidays has become a personal tradition. As the years pass by, I’ve started looking at the film in different ways. This year, I focused on Jack Skellington, the main character, and studied him from a leadership standpoint. I wonder: why did he fail? why was this such a calamity?

In case you have not seen it, let me quickly go over the key aspects of the plot.

The story takes place in Halloween Town, a fantasy world dedicated to creating this magical holiday year by year. The monsters, witches and other supernatural beings that live in it are led by our hero (and secret childhood crush) Jack Skellington, the loved and well-respected mastermind behind every year’s Halloween plan. Despite all his success, Jack is growing weary of the same routine year after year and craves something new.

Wondering through the woods he stumbles upon six secret doors leading to different Holliday Worlds, but the one that really catches his attention has the shape of a fully decorated Christmas Tree. You got it! He inadvertently enters the Christmas World, landing in soft sparkling snow. While discovering this new magic place, Jack sings one of the most iconic songs of the movie, written by songwriting genius, Danny Elfman: “What’s this?” He walks around Christmas Land wondering: what’s a gift? What’s a Christmas tree? What are the songs he hears? In a nutshell, what is Christmas?

Awed by this wonderful new place, Jack returns to Halloween Town to show his people what he has discovered. The Halloween creatures do their best to understand and share Jack’s excitement, but they don’t quite grasp what this holiday is about. Jack finally tries to convince them by “giving them what they want”, telling them the ruler of this Christmas land is the mighty “Sandy Claws” — and this! This they understood.

Although he cannot rationally explain what Christmas is, Jack announces that the citizens of Halloween Town will take over Christmas, kidnapping “Sandy Claws” and informing him of the decision that Jack will be the one delivering the toys to the kids that year. Needless to say, this ends up in disaster, with all the kids being chased and frightened by Halloween-like toys, creating chaos and fear all around.

After a while, Jack realizes his mistake and — Spoiler alert — rescues Santa and sends him back to Christmas Land to undo what has been done. The Halloween themed presents are replaced with genuine, Christmas appropriate ones, and Christmas is saved for everyone. Jack returns to Halloween Town, fully embracing his original holiday and fired up to start planning next year’s Halloween, along with all the citizens of this magical land.

Now, what made Jack such a successful leader for so many years in Halloween Town? In my opinion, this boils down to three key points:

1. Authenticity — one of the most crucial qualities any leader must have. This is the way leaders build trust, by being genuine and real. Everybody trusted Jack because they knew and understood who he was and what he stood for, what he was capable of and the kind of leader he was. This meant the citizens of Halloween Town did not have to waste time wondering if Jack had hidden agendas or if he would betray them, they could simply follow the real Jack they all trusted.

2. Energetic direction — providing direction and energy is one of the key missions of all leaders. When managing Halloween, Jack always had a plan, one he built together with the citizens of this magical land, and one he communicated in a clear and transparent way. But most of all, he transmitted his excitement and energy to everybody who worked with and for him. Leaders who are capable of doing this never have to ask anyone to do anything, as people in their teams are inspired to be proactive. The result? Team members that understand where they are going and are motivated to get there.

3. Sense of purpose — purpose is the internal compass that guides us to do what we do. Leaders that have a contagious sense of purpose build dynamic teams around them, teams that walk the same path they do. A clear and shared purpose gives any team, company or association a soul, and will be the “North Star” in the most challenging moments, and a clear objective for those who might get lost on the way.

Notedly, the moment Jack stopped sharing the Halloween Town purpose he stopped being the great leader everybody had known until then. He could no longer provide the Halloween Town citizens with direction, his energy was low, and people felt he was not himself. When Jack tried to come up with a new mission by trying to take over Christmas, he made some crucial mistakes, which ultimately led to catastrophe for all.

What did he do wrong? I have spotted three areas where I think Jack could have done a better job as a leader. By addressing the points below, he would probably have had a successful outcome.

1. Ignoring biases — it would be a lie to say we don’t have any biases, and most probably, we always will. Humans are judging creatures, we do it in order to explain what we don’t know yet and manage uncertainty. Although it is difficult to change our biases, it is important to be aware of them so that we can make better decisions.

The citizens of Halloween Town were completely biased toward anything that was scary, disgusting or spooky. When they tried to interpret Christmas, they filtered it through their biases, creating wrapped gifts that had contents that felt familiar to them, thus filling Christmas socks with zombies and bugs. Jack knew his people had these biases but chose to ignore them in order to achieve his goal on time. He even used this to his advantage, by teasing them with “Sandy Claws” and enticing them to embrace this new holiday, not by helping them understand why, but by using their biases to make everything feel familiar and therefore understandable.

Every new project, team or job will require people to manage their biases in order to fully embrace change. It is important for leaders to encourage that, and create the space and time for it, all while leading by example with an open mind and heart.

2. There is no I in TEAM (cliché and all) — if you want to go fast, go alone; if you want to go far, go together. Jack was so overwhelmed by his need to make Christmas happen, he forgot that this was not about him. He embarked in this journey alone, ignoring close friends and trusted advisors who challenged him and asked him to reconsider. He didn’t involve anyone in his planning or made use of a sounding board. He was in a hurry and wanted his vision to be executed, so he decided to take decisions on his own.

Leaders are only as good, effective and strong as the teams they build. When creating successful teams, diversity will play a crucial role, as it will ensure skill gaps are better covered and other views and voices are included to raise different issues and provide a wider range of solutions.

3. Not asking “why?” — “what’s this?” This was the only question Jack asked himself when he was in Christmas Land, he never asked why people celebrate Christmas. Understanding why we do something is closely linked to purpose, it is the motivational force behind everything we do. This is why answering what or how just doesn’t cut it.

Jack was so impressed by the beautiful and warm feeling this new holiday gave him, he forgot to ask the crucial question, “why?”. Ultimately, this meant he was unable to explain Christmas to the citizens of Halloween Town. Although he had the energy, he could not provide them with the direction, as he had no understanding of the purpose.

In order for leaders to successfully communicate and implement a new strategic direction, they must have full clarity on the purpose behind it. If they are able to transmit it, and ensure people understand it and make it their own, most of the other factors will fall in place. Direction will be clear, energy will be transmitted and shared by the feeling of walking together as a team towards something. The transparent and open communication of that purpose will support authenticity and ultimately outcomes will be more successful. However, all this will be difficult if both leaders and teams cannot unequivocally answer the “why?” question.

Talking about leadership in retrospect or analyzing a glorious movie is easy, the real challenge is taking on these lessons, and implementing them when we are leading our teams, particularly in times of change. The current social, economic and political environment calls for change, I don’t think there is a way around it. The world will need leaders that share a sense of purpose with their teams in an authentic and communicative way. The world will need leaders that embrace change, innovation, diversity and collectiveness, all while leading by example. Ultimately, the world will need leaders that ask the right questions.

And who knows, maybe Mr. Burton will change the iconic Jack song to: Why this?

Natalia Monnard



Natalia Monnard

HI! I am Nats! Curious, passionate and inquisitive, I believe in life there are no problems, only solutions. www.nataliamonnard.com