Alpha Transform Blog

Trends and impacts, interviews and insights, provoking thoughts

Alice’s allegory—Leadership lessons from Wonderland

by | Feb 20, 2018 | Insight | 0 comments

I always loved Lewis Carrol’s Alice books. As a child it was all about the fantastically colourful characters and unique situations. As I grew up it retained its charm, and I started to see extra layers of meaning. As a teen I really appreciated the commentary on logic, nonsense and where they overlap in the fuzzy or false logic that people often use to persuade others. For example:

“Then you should say what you mean,” the March Hare went on.

“I do,” Alice hastily replied; “at least—at least I mean what I say—that’s the same thing, you know.”

“Not the same thing a bit!” said the Hatter. “Why, you might just as well say that ‘I see what I eat’ is the same thing as ‘I eat what I see’!”

“You might just as well say,” added the March Hare, “that ‘I like what I get’ is the same thing as ‘I get what I like’!”

“You might just as well say,” added the Dormouse, which seemed to be talking in his sleep, “that ‘I breathe when I sleep’ is the same thing as ‘I sleep when I breathe’!”

These days, what I take from re-reading it are a range of life and leadership lessons. And I think that’s the beauty of this type of fiction, there are many interpretations and it helps you reflect on your own values and principles. Here’s my take on it and my top 5 leadership lessons from Alice’s adventures.

1. We all face ambiguity, uncertainty and paradox (riddles, nonsense and madness)

Just like Alice, as we enter the workforce we are met with many different perspectives and seemingly illogical practices. “You don’t have to be mad to work here, but it helps” is an all too common catch-cry and the sort of sentiment you’ll hear when getting to know colleagues in a new job or team. The Cheshire Cat gives Alice the same advice “we’re all mad here, so are you, or you’ve wouldn’t have come”.

As we come to accept the madness, we’re also called to challenge the nonsense, as Alice does. Someone has to question the cries of “that’s just the way we do things around here” and push for better and more efficient ways. As leaders, this is our role.

Alice struggles with this at first, but by the end of Through The Looking Glass, she has matured, become a Queen, and has mastered both her inner game (stress and emotions) and outer game (how she influences and inspires those around her).

As leaders we are called to face the ambiguity and the uncertainty and shape it. It is up to us to find a vision within the madness and lead others through it.

2. You don’t need a specific career plan

“Would you tell me, please, which way I ought to walk from here?”

“That depends a good deal on where you want to get to,” said the Cat.

“I don ’t much care where—” said Alice.

“Then it doesn’t matter which way you walk,” said the Cat.

“ —so long as I get somewhere,” Alice added as an explanation.

“Oh, you ’re sure to do that,” said the Cat, “if you only walk long enough.”

If you have a plan, that’s ok. But if you don’t, also ok. We don’t need to have a specific plan for our leadership journey, careers or lives in general. Purposive drift can work quite well. The idea is to keep learning and broadening your skills, both technically and with people.

Over time you can take opportunities that come along or seek them out. But whatever you choose to do—even if you change directions—will enrich the skills and experiences that you’ve had and enable the further step in your journey. Even if you’re not looking to climb the corporate ladder, lifelong-learning is a great way to maximise your job satisfaction and happiness in general.

A good guide for this career approach is: if you’re not learning, you’re not ‘getting somewhere’, so it might be a good time to change it up.

3. Emotions must be acknowledged

The two Alice books are full of highly emotional characters. From the Queen of Hearts who has a very short temper, to the often-distraught White Queen, from the very sad Mock Turtle to the anxious White Rabbit. Even Alice herself has to battle with and overcome her emotions.

Early in Alice in Wonderland, she can’t get her physical size under control and she cries a river. Literally. But in allowing herself to feel her emotions, Alice can then let them go, move on and make progress on her journey.

We also must remember to do this. When we just suppress the emotions we have to invest a little effort continuously to hold them down, like balloons under the water in a pool. There’s only so many balloons you can hold down before one or more come bursting up at an unfortunate moment. And even if you succeed in holding them down, it’s exhausting! Suppressing emotions also leads us to unconsciously avoid certain people and situations we need to face to be successful.

A good technique (taught to be by psychologist and mindfulness expert Cameron Aggs) is when you feel an emotion bubble up in the workplace, to just take a moment to feel the emotion, then say to yourself “yes, I’m frustrated”, or “yes, I’m disappointed” (whatever is appropriate). If you do this, you’ll be amazed how often the emotion will just fade away as quickly as it appeared. If the emotions don’t fade away, there could be deeper issues at play, and worth seeking professional support.

It can be just as useful to help others around you acknowledge their emotions so they can move past them. Whether that be staff or stakeholders, by empathising with what they’re saying and paraphrasing the emotion back to them “that sounds frustrating”, you help them acknowledge what they’re feeling and let it go, then you can move on to a practical way forwards.

4. Show courage in the face of risk and failure

The Queen of Hearts becomes a prominent symbol of risk with very real consequences. “Off with their heads!” the Queen cries at the slightest provocation. Many around her shrink from saying or doing anything for fear they may be executed. They lie, deceive and cover up their failures. Two cards spend time and resources trying to paint the white roses red because they were meant to paint them red in the first place.

These issues are seen in the workplace when leaders judge and punish failures in any way. Even subtle judgements of ideas and work that people have completed can diminish their motivation to continue to contribute above and beyond the bare minimum. Being able to motivate this discretionary effort in others is what leads to high-performing teams and partnerships, and as a leader, it’s your role to do this.

It turns out the Queen of Hearts never actually executes anyone, her bark is worse than her bite.

The lesson here is two-fold:

  1. We must create an environment where those around us know it’s ok to fail. But it also makes it an environment where it’s ok to succeed. If we act as the Queen does, our staff and colleagues won’t do anything for fear of judgement.
  2. We must realise that when we are judged by others around or above us, not to shrink away but to question what the true impact of the risk is. Many leaders in the workplace shy away from risk and thus achieve very little.

5. The importance of coaches and mentors

The Cheshire cat never answers Alice’s questions, however, he prompts her to deepen her own thinking. He provides just enough support so she doesn’t feel abandoned and alone, he seems to be always there, just out of sight. And yet, he doesn’t jump in, take over, rescue or micro-manage. He has a mischievous personality, but he plays the role of the coach well, just providing enough prompting to help Alice make her own decisions.

We can play the role of a coach with staff and even other colleagues and stakeholders. This is a very facilitative role.

“You don’t need to own the decision, just own the need for a decision”—David Beal

Just own the need for a decision and guide the group to work through and decide for themselves.


The Caterpillar takes on more the role of a mentor, leveraging his experience, he gives Alice advice as to how to address her physical size problems. The Red Queen plays this role in Through the Looking Glass. This is also a role we can play as leaders to support those around us, but we need to be careful not to disempower people by telling them what to do. Everyone needs to find their own path on their leadership journey because everyone’s situation and context is a little different.

An approach that has worked well for me in the role of a mentor is to give advice using personal examples, rather than rules that are etched in stone. For example, you could say ‘You may need to adapt this for your situation, but what worked well for me was to stand on one leg, touch my nose and hop up and down on the spot’, or whatever advice you’d recommend that’s probably going to be a lot more valuable to your mentee than that example.

Curious and Curiouser

So those were my top 5, but there are many more lessons in there I’m sure (growth, EQ, picking your battles to name a few). Perhaps a follow-up article will be in order down the track.

What are your favourite lessons from Alice’s adventures or other fictional characters?

About the author

Andrew Ramsden

Founder Alpha Transform and host of Alpha Geek Podcast

Andrew Ramsden is a speaker, trainer, coach and podcast host specialising in digital and technical leadership.

Andrew founded Alpha Transform to help organisations keep up with the ever-changing world around us.

He has a particular passion for leadership development, especially helping technical professionals level-up and unleash the great leader within.

Accelerate your technical leadership journey...

Tell me how