Not anyone, in fact, but me
Why, I could make a Christmas tree
And there's no reason I can find
I couldn't handle Christmas time
I bet I could improve it too
And that's exactly what I'll do
Hee,hee,hee
Jack Skellington
The Real Battle Is Not Technical; It's Cultural
A few evenings ago, I rewatched Tim Burton's The Nightmare Before Christmas, and midway through, I stopped observing the artistic and entertaining side and instead began seeking its deeper meaning, connecting it to my work experiences.
If you watch The Nightmare Before Christmas, you will see perfectly reflected the story of many organizations working in technology and IT that have attempted to modernize themselves. The film is a beautiful example of organizational culture that refuses to evolve. Jack has a brilliant plan. He has charisma. He has authority. And yet he fails miserably. And do you know why? Because nobody truly understood him. Nobody truly believed in Christmas in Halloween Town. They simply executed.
And this is precisely the disease afflicting many tech companies when they attempt to innovate.
Jack Skellington: The Visionary Who Imposes Without Understanding
Jack sees the future. He is the Pumpkin King, the undisputed leader of Halloween Town. His idea—celebrating Christmas instead of Halloween—is brilliant, fascinating, audacious. But here's the problem: Jack doesn't even ask the most important question: "How do I make people here truly understand this idea?"
Jack decides. Jack communicates. Jack mobilizes resources. But he doesn't create understanding. He doesn't explain the "why" of Christmas being different, why it's worth radically changing course, how people should feel Christmas, not just execute it.
In the IT world, Jack is the decision-maker who arrives at the meeting and announces: "We're migrating everything to the cloud. We're adopting AI. We're moving to agile. We start next Monday." He's right. He knows where the market is headed and what the organization's inefficiencies are. But he has no answer to: "Why should I, with 15 years of experience in the products we offer, completely change the way I think?"
Jack's cardinal sin is this: he assumes adoption is automatic with authority (or even with credibility). He assumes that if he says it, that's enough. He doesn't understand that true innovation requires shared understanding, constant practice, and internal alignment—not just external conformity.
Jack orders the citizens of Halloween Town to craft "Christmas pranks." The people do it. They do it well, even. But they do it because they obey, not because they believe. And when things begin to go wrong—when children scream in terror instead of laugh with joy when receiving gifts—the citizens of Halloween Town lack the mental tools to adapt. They have no internal compass that says: "Wait, Christmas should be different from this."
Here's the real problem: without understanding and shared ownership of innovation, you cannot manage uncertainty. And innovation is uncertainty. When the plan starts to fall apart (and it always does), you need people who have internalized the "why," not just the "what." Otherwise, you'll only see disengagement and sabotage.
Sally: The Voice of Reason, Silenced by Lack of Seniority
Sally is the film's most tragic character. She is intelligent, intuitive, sees problems before they happen. She has terrible premonitions about Jack's Christmas plan. She has data. She has experience. She is right.
But Sally has one problem: she doesn't have enough seniority to be heard.
"Jack, please listen to me. It's going to be a disaster!" Sally says. What does Jack answer? "How could it be? Just follow the pattern! This part's red, the trim is white." It's not a discussion. It's an elegant dismissal of someone who doesn't "understand" enough.
In the IT world, Sally is the experienced person who has seen different modernization attempts fail and sees warning signs in the new plan. She's the product manager who has data on what people truly use and don't use. She's the organizational psychologist who understands the company's culture isn't ready for change.
But Sally has a perceived seniority problem: she doesn't have the authority that our Jack possesses. So Sally is politely ignored.
And here's where organizational tragedy occurs: The people who see the risks withdraw from the conversation. Not because they're tired of talking, but because they understand that nobody will listen until it's too late. Sally knows her premonition will come true, so she silently prepares to manage the disaster alone—trying to save Santa Claus without help, wasting resources that could aid the project.
This is what happens in companies: your best early-warning system becomes emotionally disconnected from the project. Not because they don't believe in change, but because they see their intelligent objections being treated as "conservatism" or "resistance to progress."
The question every tech leader should ask themselves: If your smartest skeptics have withdrawn from the conversation, is that a sign your project is healthy? No. It's the opposite. It's a signal that you've lost your internal quality-control system.
Oogie Boogie: The Saboteur Who Protects His Own Power
Oogie Boogie is the perfect antagonist not because he's evil—he's evil because the system allows him to be. While Jack is distracted by his obsession with Christmas, Oogie Boogie sees an opportunity. A vacuum. An organizational confusion.
Oogie Boogie is the guardian of Halloween Town's old world. He has power, autonomy, a structure that works for him and suits him. And when Jack arrives with his radical change plan, Oogie Boogie knows one thing with certainty: he will lose influence. The monsters will follow Jack toward Christmas. The power structure will topple.
So Oogie Boogie doesn't directly fight Jack's plan. He lets it fail. In fact, he exploits the failure to consolidate his power. He captures Santa Claus. He brings the situation to total chaos. And in that chaos, Oogie Boogie becomes indispensable.
In the IT world, Oogie Boogie is the group of experienced people who know the products or services being delivered (and their weaknesses too) and derive status, power, and a sense of indispensability from that knowledge. When the innovator arrives wanting to modernize, make organizational changes, introduce new architectures, Oogie Boogie sees clearly the dangerous context: the old systems and approaches will no longer be the company's heart. The old experts will no longer be the only ones who understand how everything works.
So Oogie Boogie—consciously or unconsciously—actively sabotages the change. Not by declaring open war. But by:
- Slowing the adoption of new methodologies ("Wait, we need more planning")
- Blaming all problems on the transition phase ("See? Legacy was more stable")
- Creating knowledge silos ("Only I know how this system/process works")
- Exploiting every production incident as proof the new doesn't work ("I told you so")
What's diabolical about Oogie Boogie is that he's not entirely wrong. Legacy systems work. Old processes make sense to those who know them well, perhaps they're inefficient, but they work. Oogie Boogie isn't a fool resisting progress. He's someone who built something and is watching their creation—and their importance—be questioned.
Until your organization directly addresses the question "How do we ensure that people losing power in the new model remain involved and valued?", Oogie Boogie will continue to sabotage.
The Real Problem: The Gap Between Plan and Reality
Here's what happened in Halloween Town:
Jack had an excellent plan (celebrate Christmas). He had the authority to implement it (he was the Pumpkin King). He had resources (all the monsters were building, making gifts, decorations, etc.). He even had success metrics (how many scared children... I mean, how many happy children).
But his plan contained no shared understanding of what Christmas was.
And you know what's worse? He didn't even have a concrete plan for creating that understanding. There was no communication campaign explaining: "Here's why Christmas is beautiful. Here's how you'll feel when you see children smile instead of scream. Here's how your role will change, and why that's a good thing."
Jack said: "It will be fantastic, trust me." And everyone said: "OK, let's do it." But inside, Halloween Town's citizens remained the same: creatures accustomed to frightening, who had never considered doing anything differently.
In the IT world, this is exactly what happens when you announce "We're adopting Agile" or "We're migrating to the cloud" or "We're becoming DevOps," in phases:
- Announcement from the top (the Organizational Plan)
- Superficial compliance (we set up teams, buy tools)
- Discovery that the plan wasn't taking "root" (teams revert to old behaviors when nobody's watching)
- Frustration from above ("Why aren't they adopting the change?")
- Blame on individuals ("Teams are conservative, they don't understand")
- Silent failure (the project continues, but doesn't reach its objectives)
The difference between plan and reality is this: the plan exists in documents and meetings. Reality exists in the daily behaviors of n people who don't truly understand what's happening and why.
The Real Difficulty: Two Problems That Seem Like One
If you're a tech leader reading this, you're probably asking: "Ok, all true. But how do I do this concretely?"
Here are the two real problems you need to solve:
Problem A: How Do You Change Culture?
You can't decree cultural change. Jack tried. He ordered the monsters to celebrate Christmas with enthusiasm. Culture isn't a policy. It's a set of assumptions, behaviors, values that people have deeply internalized.
The real question isn't "How do I communicate the change?" (that's marketing). It's "How do I help people develop their own cultural transition?"
In Halloween Town, people firmly believed: "Scaring children is what we do. It's what we're good at. It's what defines us." Changing this deep assumption requires more than a statement. It requires:
- Direct experience of what Christmas is (not a description, but participation)
- Visible successes in small contexts (showing that Christmas can work)
- Revised identity ("We're not just frighteners. We're creatures who know how to create joy")
- Psychological safety (if I fail at Christmas, will I still be valued as a creature?)
In your IT case, this means:
- Not just training on new technologies or approaches, but real experience building, for example, a new service from scratch that way
- Not just a roadmap, but early wins on pilot projects where the new approach works
- Not abstract "innovation" culture, but concrete values people feel as their own ("We solve problems quickly and transparently")
- Psychological safety: if we try the new approach and it doesn't work, it's a learning opportunity, not a failure to hide
Problem B: Translating the Plan into Concrete Weekly Actions
This is Jack's greatest sin. He has a wonderful plan. He describes it beautifully (in the song "Jack's Obsession," it's almost hypnotic to hear his vision). But he doesn't do the hard work of translating that vision into concrete daily behaviors.
Jack didn't say: "Monday, we—frightening creatures—will begin studying how Christmas gifts work. Each day, a 2-hour session. We learn what it means to bring joy instead of fear. We do role plays. Practice, practice, practice."
Instead, he said: "Do it. You know what to do." And people tried to guess, misinterpreting, creating monster-Santas shooting cobwebs instead of gifts.
In your case, this means the modernization plan can't remain theoretical. It must translate into:
- Concrete weekly actions (not meetings, actions)
- Structured experiments (we pilot the new approach on this micro-project for 4 weeks)
- Behavioral metrics, not just technology ones (are developers curious to learn the new language? Are they participating in workshops?)
- Direct mentorship (not an online course, but someone sitting beside you learning while doing)
- Continuous feedback (not a quarterly retrospective, but weekly check-ins on how you feel about the change)
- Clarity on real consequences (will those adapting more slowly be supported? Will those openly resisting have space for dialogue?)
Why Without Shared Understanding You Won't Reach Your Goal
Think about this: If Sally had listened to Jack, and Jack had listened to Sally, what would have happened?
Sally would have said: "Jack, your plan is fascinating, but Halloween Town's people don't know what Christmas is. They're scared. They don't know how to relate to children who smile instead of flee. We need time to prepare the culture."
Jack could have responded: "You're right. So let's not do a total transition. Let's experiment. Take Lock, Shock, and Barrel—they're young, they're curious—and let's teach them Christmas. Let's show the others how it works. Let's build understanding slowly. Only when people truly understand it do we expand."
But instead? Jack imposed. Sally protested. Nobody listened to either. The result? Terrified creatures creating Gifts with cobwebs, zombie reindeer, and Santa Claus taken into custody.
Why without shared understanding you won't reach your goal is simple: superficial adoption doesn't hold when things get complicated.
When everything is easy, people follow your orders. But when:
- Microservices are more complex than expected
- The cloud costs more than estimated
- The new process is slower the first time
- The new system's bugs are frustrating
That's when people decide whether they truly believe in the change or go back to old ways. And that decision is based on how deeply they've internalized the "why."
Sally understood the "why" of Christmas (bringing joy to children is beautiful). But she couldn't convince others because nobody listened to her. Jack had the "what" (we're migrating to Christmas), but didn't have the "why" deeply rooted in the community.
Halloween Town's people understood the "how" (we have the tools, processes, planning). But didn't understand the "why" (why should we stop doing what defines us and what works for us?).
Without shared understanding of this "why," innovation remains an order. And orders are executed poorly when nobody believes in them.
How to Really Win: Two Pillars
If you're a tech leader wanting innovation to take root in your organization, you must address two pillars simultaneously:
Intentionally Change Culture
Don't wait for culture to change on its own. You must be intentional. This means:
Involve the Sallys in your company. Not just in meetings where they say "I have an objection," but in spaces where they can truly collaborate on how to make change possible. Transform your smart skeptics from "problems" to "co-designers of the solution."
Directly address the Oogie Boogies. Not with confrontation, but with honesty: "The new power system will be this. Here's how you stay important. Here's what we lose together and what we gain." If Oogie Boogie truly understands that change isn't a personal threat but an opportunity, sabotage diminishes.
Don't imitate Jack. No top-down impositions. Create spaces where people can discover why Christmas is beautiful. Run experiments. Celebrate early wins. Show that people embracing change thrive, not get punished.
Measure understanding, not just adoption. Don't ask yourself "How many people embraced the innovations?" Ask: "How many people truly understand why what we're proposing and implementing is better for them?" The first is a number. The second is a sign of organizational health.
Translate the Plan into Concrete Weekly Actions
Having a vision and solid strategy isn't enough. You must transform it into daily behaviors:
Create structured experimentation, not immediate rollout. Take 10% of your product portfolio/features and say: "We'll use microservices only here. We'll learn. After 8 weeks, we evaluate and decide whether to expand or modify."
Make progress visible, not plans. Not a 2-year roadmap. Rather: "This week, team X launched the first microservice, here's how it went. Next week, team Y starts."
Direct mentorship, not training. Not an online Kubernetes course. Rather: "Tuesday and Thursday afternoons, your senior architect will teach you how to architect a cloud system. You're building together."
Celebrate failures as learning. When the first experiment doesn't go as planned (and it won't), it's not a defeat. It's data you share publicly: "Here's what we learned. Here's how we'll do it differently next time."
Psychologically protect people. Those who embrace change and fail shouldn't fear losing their position or importance in the organization. Otherwise, when things get hard (and they will), people revert to old ways—not by choice, but for self-protection.
Jack's Ending Isn't Obvious
What's beautiful about the film is that Jack learns. Not immediately, not easily, but he learns.
After the disaster, Jack understands that Halloween Town can't and shouldn't be Christmas in the future. Halloween Town is Halloween Town, and that's beautiful. But it can integrate with Christmas in small, authentic ways. Sally stays by his side. Oogie Boogie is defeated. The community has learned something about itself.
This is the model to adopt:
Don't try to completely transform your organization. Seek to help it evolve, keeping what works, intelligently integrating the new. Not in isolation from charismatic leaders, but in collaboration with Sallys and even Oogie Boogies—transforming them from antagonists to participants.
And above all: don't just announce change, but embody it with concrete weekly actions, visible experiments, shared learning, and psychological safety for those brave enough to try.
Because innovation doesn't fail from lack of vision. It fails from lack of culture supporting it and concrete actions making it real in people's daily lives.
The Question to Ask Yourself Today
Do you recognize Jack in your organization? A brilliant leader who imposes vision without seeking understanding?
Do you recognize Sally? The smart skeptics who've been marginalized?
Do you recognize Oogie Boogie? The colleagues protecting their power?
If the answer is "yes" to all three, your innovation project probably isn't taking root the way you think. It's happening on paper. In documents. In meetings. But not in your people's daily behaviors and values.
And the first step to changing that is recognizing it.
It's not too late to transform Jack into someone who listens to Sally. It's not too late to give your smart skeptics a co-design role. It's not too late to be honest with your Oogie Boogies and design a future where they stay important.
But you must start now. Because every week that passes without this awareness, your organization remains frozen, like Halloween Town before Jack returned—beautiful in its way, but incapable of evolving.
If you recognize yourself in this story—whether you're Jack, Sally, or even Oogie Boogie—share it, and may it be a Merry Christmas and a good start to a year of innovation.
Bumpy sleigh ride, Jack? The next time you get the urge to take over
someone else's holiday, I'd listen to her! She's the only one who makes
any sense around this insane asylum!
Sandy Claws
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