The Pooh Paradox: Why Leaders Must Challenge "The Way We’ve Always Done It"

My friend Dr. Michael Frisina introduced me to something he calls “The Pooh Paradox.” What is that?

In one of the lesser-known but surprisingly insightful moments in Winnie the Pooh, there’s a scene where Christopher Robin is dragging Pooh downstairs by the back of his head. Thump. Thump. Thump.

Pooh, in his gentle and reflective way, begins to wonder: "There must be a better way to go down the stairs… if only he could stop bumping long enough to think of it."

And just like that, we have what Dr. Frisina calls “The Pooh Paradox.” It’s the idea that we keep doing something uncomfortable or inefficient—not because it’s the best way, but because it’s what we’ve always done.

The Lesson for Leaders Hidden in a Children’s Story

It’s easy to smile at the image of Pooh bumping down the stairs, but many leaders do the same thing every day.

• We repeat outdated processes.

• We hold onto inherited structures.

• We follow routines that once worked—but no longer serve the mission.

And we do it not because we’ve thought it through, but because we’ve never stopped long enough to ask if there’s a better way.

This is the heart of innovation in leadership: learning to pause, question, and reimagine. Because good leadership isn’t about preserving comfort zones—it’s about pursuing clarity and effectiveness.

Why It’s So Hard to Challenge the Norm

Here’s the truth: questioning “the way we’ve always done it” can feel threatening. It requires humility to admit that something isn’t working—and courage to explore alternatives. But if we don’t pause and evaluate, we’ll find ourselves bumping down stairs year after year, mistaking tradition for wisdom.

This doesn’t mean we abandon everything that came before. It means we treat our systems, strategies, and structures as tools—not sacred relics. If they no longer serve the mission, they must be adapted—or replaced.

Becoming Leaders Who Learn

To overcome the Pooh Paradox, leaders must become learners. Here’s how:

✅ Ask “Why?” more often. Why do we do it this way? Why do we meet like this? Why are we still using this model?

✅ Listen to fresh perspectives. Sometimes the most insightful voices are the newest ones in the room. Invite honest feedback—and actually hear it.

✅ Give permission to experiment. Innovation thrives when people are free to try, test, and learn. Failure isn’t fatal—it’s formative.

✅ Measure success by impact, not comfort. A strategy is only successful if it helps you move the mission forward—not if it just keeps everyone happy.

Pooh may be a silly old bear, but he was onto something. There is a better way to go down the stairs. And chances are, there’s a better way for your team, ministry, or organization to operate too.

As leaders, our job isn’t just to keep things running—it’s to keep learning.

Innovation begins the moment we stop bumping—and start thinking.

Want help evaluating your culture, structure, or strategy? I help leaders and teams rethink how they lead so they can serve with greater clarity, creativity, and conviction.

📲 Book a Free Strategy Call with me today!