Christopher Robin on Leadership

By Tim Cummuta

Updated Over a Week Ago

Minute Read

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Very few people have realized what I have known for a while. Christopher Robin is one of the great leadership gurus of the late 20th century.

Christopher Robin has faced an ever-changing and challenging environment and hosts many misaligned personalities.

Through Christopher Robin’s leadership skills and unique management style, he continually resolves issues in each and every story.

As with all leaders, he faces the challenge of overcoming difficult personalities or, in some cases, focusing individual differing personalities into a consistently successful organization.

Leadership and Personality Types

Imagine working with some of the personalities he is faced with on a day-to-day basis.

There is a myriad of issues here with a wide variety of personalities.

We will examine just three here:

  • Tigger
  • Eeyore
  • Winnie the Pooh

Although there are many other individuals with which Christopher Robin must interact to build a productive team, these three individuals represent the spectrum of personalities and give us an insight into Christopher Robin’s management challenges.


Tigger is a ball of energy and, in his own words, is always “the smartest and the best one around,” just ask him.

Tigger is quick to jump at any task. This is a great attribute in most cases. Tigger is an extremely creative but misguided individual. Tigger often causes more grief than most other individuals in the organization. He often breaks far more than he fixes.

Christopher Robin sees Tigger as aggressively overestimating his own abilities to his and the organization’s detriment. Tigger often leaps before he looks and usually lands with a crash.


Eeyore is humble, too humble, and very negative. There is not much that Eeyore can’t complain about.

Eeyore is friendly and kind, as is most of Christopher Robin’s team. Most other individuals ignore his negativity, generally stay away from him, or attempt to change his negative feelings through positive encouragement. The latter usually gets the ‘Thanks for noticing” response from Eeyore.

Christopher Robin thinks that Eeyore is too passive and has a poor attitude about generally everything.

Winnie the Pooh

Winnie the Pooh is extremely good-natured but does not always think things through.

Pooh, as everyone calls him, is always willing to help. And he is kind. These types of workers are good to have around. They tend to keep their attitudes up and friendly. In Pooh’s case, though, he tends to find himself in predicaments that are often hard to turn around, such as getting his nose stuck in a honey jar.

Christopher Robin has rightly deduced that Pooh is properly active but not focused clearly on organizational goals.

Herding Cats

Management, many times, is quite a bit like herding cats – seemingly almost impossible.

Christopher Robin realized that these three individuals run the gamut of personality types he sees in his organization. Tigger is the upper limit which is aggressive to a fault. Eeyore is at the lower limit or passive to a fault. Finally, Winnie the Pooh is in the middle. Pooh is active but is not focused well. Christopher Robin considers Pooh to be at the correct position on the scale but realizes Pooh needs more direction.

Leaders usually believe that the Tigger types are best, especially when considering salespeople. Of course, no one likes to deal with aggressive salespeople.

In reality, aggressive individuals such as Tigger often create difficulties in organizations. This is because action usually takes precedence over analysis. This can cause more bad than good which is what typically happens for Tigger.

There is a difference between the ability to take action and aggressiveness.

Eeyore types are usually good workers if left alone. They can often be an emotional drag on an organization in dealing with change. Many Eeyore types will find it extremely difficult to deal with change. Eeyores have a tendency to leave organizations during difficult times.

To some, it may appear to be the best for the organization if Eeyores do leave. But it usually hurts an organization to lose experienced, good workers.

Focus on the Right Issues

When faced with the predicaments that Christopher Robin’s team finds itself in from time to time, Christopher Robin has learned to focus his organization on the right changes to bring them in line with the organization’s goals and mission.

Working with his team, Christopher Robin realized early on that personal development was something his whole team needed. On the spectrum from aggressive to passive, only Winnie the Pooh had the right motivation, attitude, and activity level.

  • Pooh needed to focus and prioritize his actions better, so Christopher Robin began to work with Pooh on goal setting. Christopher Robin found great material on About Leaders that helped him to put together a realistic training program for Pooh. Pooh is now much more organized and focused.
  • Tigger needed to learn to slow down and think through his potential actions. He needed to move down on the activity spectrum, more toward Winnie the Pooh. It is great that Tigger is so willing to take action. Christopher Robin knows that taking action is not enough. Taking the right actions at the right time is more likely to bring about a successful outcome. Christopher Robin believes that having Tigger work more closely with Winnie the Pooh will show the difference between the right kinds of actions and jumping too soon into something.
  • Eeyore needed to learn that attitude is everything. He needed to have a better self-image and outlook on everything. Christopher Robin appreciates Eeyore’s work ethic, so he is not willing to lose him. Instead, Christopher begins praising Eeyore while bringing his accomplishments to the notice of other individuals in the organization. Over time more and more of those who work with Eeyore begin to acknowledge Eeyore’s abilities and actions. Christopher Robin has noticed a marked improvement in Eeyore’s attitude at work.

Building Self Esteem

Christopher Robin believes the actions he has taken can also be useful to the rest of his team.

He finds each of them in different places on the spectrum, from aggressive through active to passive in their attitudes and works ethics. He focuses his team on becoming active, not passive, and avoiding going too far and becoming aggressive.

Christopher Robin decides to include motivational and personal development training in the routine training programs within his organization.

He feels everyone can benefit professionally and personally from self-development.

Christopher Robin also sees that better attitudes and focused efforts from this type of training have also been beneficial to the organization as a whole.

What Are Your Thoughts on Christopher Robin and Leadership?

If you have ideas that you feel like sharing that might be helpful to readers, share them in the comments section below. Thanks!

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Tim Cummuta
Tim Cummuta
Tim is a Business Consultant in Strategic Planning, Productivity, HR, Sales & Marketing, and Risk Management. He has a Master’s Degree in Financial Planning and is pursuing a Ph.D in Organization & Management at Capella University.
  • Jon Matsuo says:

    I enjoyed the article, it really comes alive with characters that are familiar. Tiggers are great becasue of their energy and they get things done. I’d help them succeed by giving them some structure, like a checklist, before they could commit any resources. If ego is a problem, we can use that checklist to help him insure that his projects end up great, and that he is not overstepping his bounds.
    Your suggestion that they operate as a team would help Pooh and Eeyore overcome their issues too. I seem to notice that they usually are very independent in their doings. All would benefit from some team-building!

  • Tim Cummuta says:

    Thanks Jon. I enyoyed you additions also.

  • Ajay Kulkarni says:

    Hi Tim,
    Thank you for sharing great article. It is so eloquent to read. Challenge for any leader is how to balance the individual profiles in a team and make them cohesive for common purpose.
    Season’s greetings
    Ajay Kulkarni

  • Tim Cummuta says:

    Absolutely Ajay, the bigger the organization you are working with the greater the degree of difficulty. The key, as you have stated, is to get everyone to work productively as a team while also enhancing each individual’s performance. Finding internal personal motivators and structuring the environment to maximize each person’s positive capabilities and minimize the negative attributes will go a long way to building one’s self esteem and increasing productivity.

  • Arlette Capistrano says:

    Great read Tim! It got me thinking who falls under the likes of the 3 characters in my team.
    I would very much like to read about the rest of the characters. Maybe piglet is the “yes man” will do everything pooh tells him to do?, whereas OWL is an intellectual smooth talker, the kind who talks his way through things, seems to be working, but actually getting very little done?
    Would make for a good management 101 book. Consider it.

  • Tim Cummuta says:

    Thanks Arlette, I’m sure each of the characters can demonstrate unique individual personality types. Your analysis of the Owl and Piglet are right on. It’s a challenge just as Christopher Robin faced to keep the unique and differing personalities focused and productive. Maybe there is a book here!

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