Coaching and leadership lessons from Winnie the Pooh

My life coaching tutor mentioned to me there were coaching and leadership gems in the story of Winnie the Pooh. For three decades, I haven’t really seen it that way until today. So I went to do some research. I felt moved as the analysis of Pooh’s story was so heartwarming, I felt compelled to share! And did you know there was a National Winnie the Pooh day (Jan 18)?

So, what can we learn from Winnie the Pooh and his friends?

“Life is a journey to be experienced, not a problem to be solved.”

Happy people do things differently. Managing our negative thinking can have a huge impact on our mental and emotional health.

I was speaking with my boss recently around DE&I, and we wondered if it was personalities we were leading and managing in teams, or ethnic diversities, or both in fact? Winnie the Pooh came into my mind one evening whilst I was reflecting on this conversation. I always believed that managing people was the hardest and most interesting thing to do in the world. It always required me to be creative and innovative, as I’m challenged to embrace the quirks of each team member. If we didn’t do that, we weren’t going to be very successful altogether.

Winnie the Pooh - the kind and friendly honey loving teddy bear belonging to Christopher Robin was a genius, a genuine and great team leader. Pooh as leader of the group has a knack for being very optimistic during times of despair. A courageous one in tough times, he is usually the one consulted when trouble looms. Pooh leads as a bear of very big heart, empathy and compassion. He’s had to unify a mix of very unique and difficult personalities throughout each story and chapter of the book towards a happy ending.

Starting with Piglet, he can be considered as Winnie’s 2IC, the deputy team leader. It is interesting because Piglet is a timid character most overcome by fear and anxiety, and sometimes seems a little bit jealous. Piglet also has speech impediment that causes him to stutter. Through Winnie the Pooh’s gentle coaching and encouragement, Piglet actually displayed some of the most amazing bravery, loyalty and accomplishments in the stories. It reminds us to help our team members who are facing a fear to move forward. Maybe we can learn from Pooh to “walk” with them through something difficult. We get to watch these team members develop confidence and might discover some potentially amazing leaders when we take the time to encourage.

Next, we have Tigger. Tigger is the most visible team member who is often overly confident, reckless and fairly thoughtless. People who are like Tiggers are energetic and exciting to be around. Tigger is extremely loving and friendly, and he means well and tries his best to be of support to his friends. Tiggers tend to think they are gifted in every area and take on more than they can actually accomplish. Pooh was a master at managing Tigger. Tigger would say that every task is something “Tiggers do best”. When you manage a team, make sure you control the delegation of team tasks to ensure that the Tiggers on your team can indeed do what “Tiggers do best”.

Eeyore has a pinned on tail, is always glum, cynical, moody and pessimistic. He’s probably an overly cautious team player. Eeyore is always reluctant to go-along with the group. He holds his opinions to himself silently thinking nobody will actually listen to him. In life, it’s in fact that the negative person on you team just needs to be heard. Eeyore keeps losing his pinned on tail, doesn’t like it, but still agree that nothing better can replace it. It’s like he secretly enjoys having something stuck on his ass. Perhaps in private, they need to be reassured that their concerns are heard so that the whole team can benefit and work through the issue together. If could be that Eeyore is glum because he thinks he has no real value. If you listen like Winnie the Pooh, you will find your team unifies, especially with the Eeyore’s. They can be pretty insightful and quite reliable in general.

Rabbit is rules based, obsessed with processes, planning and order. They are the ones at your workplace who knows the organisations’ code of conduct, policies, and legislations off their head and have been there for a long time. They dive into these documentations and ask for explanations, and perhaps have undergone several management iterations at work and have grown intolerant for quirks. However, they are also the go-to person for all the details and leadership when the time calls for it! Helping the Rabbits in the team focus on the right details becomes the responsibility of the team leader. Pooh often have to remind Rabbit of the goal and redirect him to see the bigger picture.

Roo is the youngest team member, the intern rookie or graduate. He is cheerful, upbeat, energetic, and impressionable. We can see Roo being close friends with Tigger in the stories. Here, it is important to know that as the team leader, members like Roo needs proper guidance, structure and support. Otherwise, we might see the Roos adopting non-ideal habits by learning from the most colourful member, but not necessarily the wisest. Having a young member on the team means guiding and moulding their future. Roo’s mum - Kanga, is protective of Roo. It serves as a reminder that outside work, colleagues like young Roo have a worried parent they need to return home to. As a team leader, you need to make sure the younger members have a positive growth experience. Pooh is always asking Roo questions to help him think for himself, just like a life coach.

Last but not least, we have Owl. Owl is the wise one, old and full of wisdom, however he lacks the most technical skills although very intellectual. We need to understand that his best skill is in the strategic thinking and planning, but not the actual tactical know-hows of given tasks in any project. Understanding this allows the team leader to maintain the integrity of your Owls, while building on their true value as a thinker. As a team leader, it is important to help the “senior” members of your team continue to learn and develop. After all, they most probably would have “been there and done that” already in their younger days. When we grow old, we’d also wish our younger leaders will treat us with kindness and respect. Pooh always treats Owl with respect and gently helps him engage with the younger members of the group.

Here are 5 more of my favourite quotes from Winnie the Pooh:

1. “You are braver than you believe, stronger than you seem, and smarter than you think.”

2. "Sometimes the smallest things take up the most room in your heart."

3. "If you live to be a hundred, I hope I live to be a hundred minus one day, so that I never have to live a day without you."

4. "Any day spent with you is my favorite day."

5. "The most important thing is, even when we're apart... I'll always be with you..."