The wizard, the witches, and your skills strategy: 5 wicked lessons leaders forget

Because every skills journey has a Wizard, a Glinda, and an Elphaba whether leaders admit it or not.

Some people watch Wicked for the music. I watch it and think, “Wow… that’s exactly what skills transformation feels like.” The hype, the hope, the heartache, the hero who gets miscast as the villain..it’s all there. And just like in Oz, your skills journey will absolutely feature a Wizard, a Glinda, and an Elphaba even if you don’t recognize them at first glance.

This weekend, after watching the new Wicked movie (again), I started reflecting on how perfectly this story mirrors the twists and turns of skills transformation. Here are the five lessons leaders often forget, but shouldn’t.

You start this journey imagining a shiny, skills-powered future with dazzling dashboards, seamless systems, thrilled leaders, and employees joyfully clicking through elegant experiences.

But here’s the Wicked truth:

If you don’t plan for hiccups, dependencies, and political flying monkeys, the Emerald City can turn into a place you want to run from.

A beautiful vision without realism creates disillusionment. A great strategy anticipates complexity and builds with flexibility.

In Wicked, the road to Oz twists, turns, stops, and surprises. Skills transformation is no different.

You’ll detour into job architecture. You’ll pause to clean skills data. You’ll reroute when technology doesn’t behave. You’ll face moments where the trees throw apples.

And that’s normal.

The magic isn’t in staying on a perfect path, it’s in surrounding yourself with the right companions who can offer expertise, guidance, and hands-on support when things get complicated.

I love our tech partners, but we need to talk about the Wizard phenomenon.

Vendors are incredible marketers. They paint a utopia of real-time insights, frictionless experiences, perfect integrations, and AI that practically sings “Defying Gravity.”

But sometimes, what’s behind the curtain is:

• A prototype
• A future roadmap item
• A demo environment that performs better than reality
• A capability that isn’t production-ready yet

Before you buy:

👉 Ask to get hands-on in the sandbox

👉 Validate the core capabilities

👉 Confirm what’s live today, not what’s “coming soon”

Trust, but verify. Always look behind the curtain.

Let’s be honest: HR walks into skills transformation with a reputation that’s… complicated.

Leaders may see HR as too process-heavy. Employees may see HR as protecting the business first. Somewhere along the way, HR becomes the Elphaba: misunderstood before the work even begins.

Changing that narrative requires a Glinda..the business.

HR + the business must co-lead this story so employees see skills transformation as:

• A change for good
• A change that simplifies work
• A change that improves performance
• A change that supports growth, mobility, and opportunity

When HR and the business stand united, the organization stops seeing “wicked” and starts seeing value.

Madame Morrible knew one thing: Repetition creates belief.

Skills transformation needs the same mindset.

This isn’t a newsletter. This isn’t one town hall. This isn’t a page on the intranet.

This is marketing.

To succeed, your messaging must:

• Build awareness
• Generate engagement
• Drive adoption
• Create affinity and loyalty

Share updates everywhere in expected places, unexpected places, and all the places employees frequent daily. And absolutely enlist Marketing. You’re building a brand around skills, not distributing information.

If you build it, they may come. If you say it 1,000 times, they will believe it.

Wicked is whimsical, emotional, and deeply human. So is skills transformation.

But it takes more than aspiration or spells to get it right.

You must:

💥 Pop the myths

💥 Dismantle false narratives

💥 Challenge assumptions

💥 Build a strategy grounded in reality, culture, and business need

When you do that, your organization and your people will not only move forward…They’ll defy gravity.