Everyone Has An Eeyore: Leadership Lessons from the 100 Acre Wood

Jacie MaslykBlog, Innovate Better, Lead Better

In This Post:

  • Leadership lessons from a favorite childhood cartoon: Winnie the Pooh!
  • Practical ideas to promote positivity from your “Eeyore” staff members.

Everyone’s tale of leadership starts in its own unique way.  Some stories are a wild adventure. Some might take complex pathways through an enchanted land, encountering twists, turns, and challenges.  Other leadership stories are light-hearted and feel more like a frolic through the 100 Acre Wood. When you take on a role as a school leader, you accept the awesome responsibility to move your school forward.  With that responsibility comes opportunities for great joy as well as immense challenges.

Some of those challenges come in the form of making difficult decisions, driving instructional initiatives, and moving all educators forward to transform your school.  

The educators on your team may come with different levels of experience, different backgrounds, personalities, and interests, each possessing their own unique character traits.  These differences help to create a diverse group of educators who can work collaboratively to make a positive impact on kids. Whatever special qualities and skills our team brings to the table, ultimately we all want teachers who will make their passion for teaching a part of the story. 

Whatever special qualities and skills our team brings to the table, ultimately we all want teachers who will make their passion for teaching a part of the story. Click To Tweet

Consider Winnie the Pooh and his friends from the 100 Acre Wood.  This group of characters possesses some traits that we might also see in our schools. Maybe these characters don’t perfectly align with your staff, but there’s a chance you just might have a Pooh or Rabbit of Tigger.

School Leaders, Know Your Characters

Can you relate any of these friends in your school?

Maybe you have some overexcited anxious Tiggers bouncing around and making a mess of everything. 

Perhaps there are some uptight Rabbits who can’t take any chance of someone messing up their garden.

You have your scared little Piglets who don’t want to take any chances. 

Then, there are your Christopher Robins, the adventurous, risk-takers.

Are there some know it all Owls that tell everybody else what they need to be doing?

Surely, you have some Kangas that just wanna mama and take care of everyone. 

Of course, there are our Winnie the Poohs that just roll with the punches and are a good friend to all. 

And then you have your EeyoresYou know, the “woe-is-me” donkey who grumbles throughout the forest.  Eeyores bring a rain cloud to a parade, the turd to the punch bowl. They make Debbie Downer look like the life of the party. Simply said, they are just never able to turn that frown upside down. 

So obviously you’re already visualizing the Eeyores and your school culture as you read this blog. Without a doubt, Eeyores can dampen your school culture. Maybe even ruin it.  

Leadership Lessons from Eeyore

Most traditional leadership advice suggests that leaders ignore the Eeyores in their organization.  In most cases they fortify themselves among like-minded staff members, resisting change at all costs.

Leaders who accept this advice place themselves at the mercy of the influence Eeyore holds over other staff members that are vulnerable to joining them on the negative, feel sad train. The mindset has always been “They can’t be changed, so don’t waste time on them.

We must strongly challenge this mindset. Instead of ignoring these people in your culture, we must listen to them. We must try to help them reconnect with their WHY!

Instead of ignoring these people in your culture, we must listen to them. We must try to help them reconnect with their WHY! Click To Tweet

The stereotypical Eeyore does not normally come from whippersnapper teachers new to the profession. Typical Eeyores come from a demographic of veteran educators who have endured countless initiatives, protocols, mandates and administrative changes over a period of time. This causes them to lose their focus on what really matters. 

Eeyore sees a new administrator and thinks, “Oh great, someone new, that wants to start a bunch of new stuff and then leave in two years...Oh, bother.

Somewhere along the way, they stopped believing they matter in their contribution to the mission of the school. They’ve forgotten that everyone can influence the culture of your school.  Therefore, they resort to negativity as a way to sound their voice.

Always remember: It is easier to complain about the problem than actually contribute to the solution. 

Leaders, Empower Your Eeyores

As leaders, we need to connect with them. We need to hear them and help them find their true purpose again. Eeyores need to know that we are listening.  We need to lift them up and find ways to show that their voice matters. That they are valued in the school culture. 

The next step may blow your mind, but we challenge you to empower them. 

Yes, that is right, empower the Eeyores to channel their positive energy to make a difference.

Alienation never works, it only compounds the problem. It is not a caring problem. It is a purpose problem with Eeyores.  Top-down initiatives lose their luster when you have no voice in the process.

Give Eeyore a voice and Eeyore will care. Give Eeyore a meaningful role and Eeyore will contribute.  

Leadership Lesson: Everyone Matters

One reason why the friends from the 100 Acre Wood are a good team is because they all contribute something different.  Every character has a role to play.

Tigger gets everyone motivated with a wild idea for a new adventure. Christopher Robin maps out the plan.  Piglet reminds the group of potential barriers. Kanga reassures everyone that they can accomplish their goals. Rabbit makes sure that everything is in order. And Pooh gives everyone a big hug before they get going. 

Each friend provides something that will make the group stronger, more cohesive. They all support one another, but in their own unique way.

Your school team may resemble the 100 Acre Wood with each character sharing their positive traits, as well as their character flaws.  We often appreciate our Poohs, our Tiggers, and our Kangas, but let’s rethink what we thought about our Eeyores. 

Chase every opportunity to lift them up and show them that their contribution is important. 



This collaborative post was inspired by a connection made at the Teach Better Conference 2019.

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An educator for the last 19 years, Don Epps, has served as a classroom teacher, coach, high school principal and is currently a middle school principal. The #ChasingGreatness Principal has been featured in national publications for stories of school culture transformation in creating what is now known as“Frosty Moments”. Epps also is known in the education world for his uplifting videos posted on social media that features his own unique blend of motivation, comedy and inspirational content that promotes positivity. Connect with Don on Twitter @DonEppsEDU, Instagram @doneppsedu or email him at coachdonepps@gmail.com.


An educator for the last 22 years, Dr. Jacie Maslyk, has served as a classroom teacher, reading specialist, elementary principal, and assistant superintendent. She is the author of STEAM Makers: Fostering Creativity and Innovation in the Elementary Classroom, Connect to Lead: Power Up Your Learning Network to Move Your School Forward (ISTE), Remake Literacy: Innovative Instructional Strategies for Maker Learning and Unlock Creativity: Opening a World of Imagination With Your Students. Jacie is a featured blogger with Demco, Defined STEM, and Education Closet, as well as maintaining her own blog, Creativity in the Making at www.jaciemaslyk.blogspot.com . Jacie has been named a featured speaker for FETC 2020 and will also keynote the Virginia Children’s Engineering Council annual conference in February 2020. Connect with Jacie on Twitter @DrJacieMaslyk or email her at jaciemaslyk@gmail.com.