Curious and Curiouser: What Wonderland Can Teach Us About Leadership

Dr Srabani Basu, Associate Professor, Department of Literature and Languages, SRM University AP

Leadership has become an extremely serious business. We have leadership competencies, leadership pipelines, leadership dashboards, leadership retreats, leadership summits and leadership development programmes where perfectly sensible adults are occasionally asked to build towers out of spaghetti so that somebody can determine whether they possess strategic agility. We measure emotional intelligence, executive presence, resilience, adaptability, decision-making and the mysterious ability to “think outside the box”—usually while sitting inside a conference room shaped exactly like one. Perhaps we have been looking for leadership wisdom in all the wrong places. Maybe one of the finest leadership schools was never Harvard, INSEAD or a corporate boardroom. Maybe it was Wonderland. After all, where else would you find uncertainty, disruption, irrational authority, changing rules, identity crises, impossible deadlines, contradictory instructions, disappearing colleagues and meetings that appear to have no discernible purpose? Wonderland is practically an organisation.

And what a leadership faculty it has! Alice, the Mad Hatter, Absolem, the Cheshire Cat and the White Rabbit would probably never survive a conventional leadership competency assessment, which may be precisely why we need them. Alice arrives without a designation, job description, reporting manager, induction programme or five-year strategic plan. She does, however, possess something considerably more dangerous: curiosity. She asks questions. Why? Who are you? What do you mean? How does this work? Why should I accept that? These may appear to be the questions of a confused child, but they are also the foundations of critical thinking. One of the greatest dangers in leadership is not ignorance. Ignorance can be corrected. The greater danger is certainty that has stopped examining itself.

Organisations accumulate assumptions the way old houses accumulate dust. “This is how we have always done it.” “Management will never agree.” “Employees are resistant to change.” “Customers want this.” “Young people lack commitment.” “Senior people cannot adapt to technology.” Repeat an assumption often enough and it gradually stops sounding like an assumption. It becomes organisational truth, acquires a chair, gets a nameplate and eventually starts attending meetings. Then Alice walks in and commits the unforgivable act of asking, “But why?” Suddenly the room becomes uncomfortable. That discomfort may be the beginning of leadership. Curiosity is not the absence of knowledge; it is the refusal to allow knowledge to become a prison.

Alice also keeps changing size, making her remarkably qualified to teach adaptive leadership. One moment she is enormous; the next she is tiny. Doors that were accessible become inaccessible. Spaces change in relation to her. Leadership works similarly. A style that succeeds brilliantly with one team may fail spectacularly with another. Decisiveness that saves a team during crisis may become authoritarianism during collaboration. Empathy that helps during conflict may become avoidance when a difficult decision has to be made. Leadership is not about discovering one magnificent style and carrying it everywhere like an executive briefcase. Sometimes a leader must become larger and occupy the room. Sometimes the leader must become smaller so that others can occupy it. Knowing the difference may be more important than knowing fifty-seven leadership theories.

And then, floating somewhere in Wonderland’s philosophical haze, sits Absolem. He does not ask Alice about her KPIs. He does not want to know whether she has achieved her quarterly targets. He asks the far more terrifying question: “Who are you?” Imagine replacing the annual appraisal form with Absolem sitting across the table asking that question. Half the corporate world would immediately apply for casual leave. Yet beneath that deceptively simple question lies something leadership development frequently neglects: identity precedes technique. We teach leaders how to communicate, delegate, negotiate, influence and manage conflict, but rarely ask who is doing the communicating, delegating and influencing.

A leader who fundamentally believes leadership means control may learn sophisticated communication skills and simply use them to control people more elegantly. A manager who needs constant validation may learn delegation techniques but continue interfering because another person’s competence feels threatening. Someone terrified of appearing weak may attend twelve emotional-intelligence workshops and still confuse vulnerability with incompetence. Before asking, “What should I do?” Absolem forces us towards the more uncomfortable question: “Who am I while doing it?” Leadership is not merely a collection of behaviours. Behaviour grows from identity, beliefs, values and assumptions about ourselves and others. No competency matrix, however beautifully colour-coded, can answer Absolem’s question for us.

Absolem also demonstrates another increasingly endangered leadership quality: he does not rush to provide answers. He makes Alice think. Modern leadership has developed a peculiar addiction to answering. Leaders are expected to know. Consultants are hired because they supposedly know. Experts are invited because they definitely know. Meetings frequently become competitions in which people throw answers at problems before anyone has properly understood the question. Perhaps leadership is not always about giving people better answers. Sometimes it is about giving them better questions. A powerful question does not create dependence on the leader; it awakens thinking in the other person. Absolem, without a leadership certification in sight, seems to understand this rather well.

Then appears the Cheshire Cat. Or partially appears. Or disappears while leaving the grin behind, which may be the most sophisticated hybrid-working arrangement ever designed. When Alice asks which way she ought to go, Cheshire essentially tells her that the answer depends upon where she wants to get to. There, tucked inside an absurd conversation between a girl and a disappearing cat, sits half the literature on strategic leadership. Organisations are extraordinarily fond of movement. New initiatives, new software, new committees, new policies, new strategies, new transformation programmes. Everybody is running. The White Rabbit is delighted. But movement is not direction. You can run exceptionally fast and still arrive efficiently at the wrong destination.

The Cheshire Cat therefore asks the question that every leadership team should confront before producing another strategy deck: where exactly are we trying to go? Strategy begins not with speed but with orientation. Cheshire also reminds us that perspective is not reality. Finance sees cost, marketing sees customers, HR sees people, operations sees processes, senior management sees strategy and the employee sees Monday morning. The customer, meanwhile, may simply see a website that refuses to accept the password. Everyone is looking at the same organisation, but nobody is looking at the whole organisation. Leadership maturity begins when we stop confusing our particular window with the entire landscape. “We’re all mad here” suddenly begins to sound less like a diagnosis and more like epistemic humility.

No discussion of leadership in Wonderland would be complete without the White Rabbit, patron saint of corporate urgency. “Oh dear! Oh dear! I shall be too late!” Every organisation has White Rabbits. Some organisations appear to be entirely managed by them. Urgent email. Urgent meeting. Urgent reminder about the urgent meeting. Urgent follow-up asking whether you have read the urgent reminder about the urgent meeting. The subject line says URGENT, preferably followed by three exclamation marks so that punctuation itself experiences anxiety. The White Rabbit teaches leadership largely by negative example: urgency is not the same as importance.

A culture permanently operating in emergency mode eventually loses its ability to distinguish fire from smoke, smoke from steam and steam from somebody quietly making tea. Leaders who treat everything as urgent do not create agility; they create cognitive exhaustion. The finest leaders understand when speed matters and when slowness is intelligence. Some decisions require immediate action; others need silence, reflection and perspective. Constantly pulling up a plant to check whether its roots are growing is not performance management. It is horticultural murder. Leadership needs the wisdom to know when to accelerate and when to stop staring at the watch.

And speaking of tea, we must finally approach the Mad Hatter. Please remove all conventional management frameworks before entering. They may not survive. The Hatter represents perhaps the most neglected leadership capability of all: the ability to disrupt the frame itself. Most problem-solving takes place within accepted boundaries. “How can we improve this process?” The Hatter might ask, “Why does the process exist?” “How can we make this meeting more productive?” He might wonder, “Why are you having the meeting?” “How can employees adapt better to this policy?” The Hatter may quietly pour another cup of tea and ask, “Has anybody considered whether the policy deserves to survive?”

This is not contrarianism for the pleasure of causing chaos. It is frame-breaking thinking. Innovation rarely begins by answering an existing question more efficiently. It often begins when someone discovers that everyone has been answering the wrong question. The Hatter would probably be disastrous at maintaining order, but magnificent at disturbing intellectual complacency. Every leadership team needs a Hatter—not necessarily someone who pours tea into inappropriate objects, but someone who has permission to say, “This makes absolutely no sense.” Ironically, organisations frequently announce that they value disruptive thinkers until an actual disruptive thinker appears. Then someone quietly calls HR.

The Hatter’s tea table also offers an unexpected lesson in psychological safety. Absurdity is permitted there. Ideas collide. Language misbehaves. Logic stretches. Possibilities emerge because correctness has temporarily loosened its tie. Creativity requires spaces where people can produce unfinished thoughts without immediately being judged for them. New ideas are rarely born wearing suits. They arrive untidy, incomplete and occasionally ridiculous. If organisations demand that every idea appear respectable at birth, they will produce very few original ideas. Sometimes leadership means protecting the tea table long enough for nonsense to discover that it contains a possibility.

Somewhere among Alice’s curiosity, Absolem’s self-inquiry, Cheshire’s perspective, Rabbit’s urgency and Hatter’s magnificent disruption lies a leadership model far more interesting than the heroic individual standing confidently at the top of an organisational pyramid. Alice asks us to question assumptions. Absolem reminds us to examine the identity from which we lead. Cheshire teaches us to distinguish movement from direction and perspective from reality. White Rabbit warns us about mistaking perpetual urgency for productivity. And Hatter reminds us that occasionally the most intelligent response to an established system is to ask whether the system itself has gone mad.

Perhaps this is exactly the leadership education we need for an increasingly uncertain world. The future will not arrive carrying a neatly bound Standard Operating Procedure. Technology will change, professions will mutate, artificial intelligence will challenge old assumptions about expertise, employees will question inherited hierarchies and problems will stubbornly refuse to remain inside departmental boxes. When the map no longer resembles the territory, following the map more obediently will not save us. We will need Alice’s curiosity to notice what has changed, Absolem’s courage to ask who we are becoming, Cheshire’s wisdom to ask where we actually want to go, Rabbit’s warning to distinguish meaningful speed from frantic motion, and Hatter’s audacity to ask whether the question itself needs to be thrown into the teapot.

Maybe Wonderland has been whispering the real lesson about leadership all along. The world does not particularly need more leaders who have all the answers. It needs leaders capable of remaining curious when answers collapse, thoughtful when everybody else is running, playful when certainty becomes rigid, courageous enough to question authority—including their own—and humble enough to recognise that their map may never be the territory.

So, the next time someone proposes another leadership framework containing seventeen competencies, forty-three behavioural indicators and a nine-box matrix, perhaps invite Wonderland into the meeting. Let Alice ask the uncomfortable question. Let Absolem examine the identity hiding behind the designation. Ask Cheshire where exactly everyone thinks they are going. Hide the White Rabbit’s watch for ten minutes. And give the Hatter the chair.

On second thought, do not give the Hatter the chair.

He will probably ask why leadership needs chairs, pour tea over the organisational chart and appoint the teapot as Chief Possibility Officer.

And that may be precisely when the organisation finally begins to think.