From Guarding to Guiding: What the Next Generation Actually Needs from Leadership

While designing a strategic approach to organisational leadership for a non-profit youth organisation, I found myself asking a different question:

What do today’s youth—Gen Z and beyond—not just need, but want from mentorship as we begin handing over the reins of leadership?

Because this transition is already underway.

It also struck me that when consultants are engaged to design programmes and plans—no matter how skilled or well-intentioned—they inevitably bring their own biases.

These biases shape recommendations. They shape structures. And often, they result in systems being imposed onto others… even if unintentionally.

This is why I continue to come back to a simple principle:

Move away from hard rules.
Move toward guiderails.

Not the absence of structure—but a different kind of structure.

An approach where doing the right thing, simply because it is the right thing to do remains central.

Where guiderails exist not to constrain, but to guide behaviour toward a shared vision, purpose, and goals—anchored in a set of collectively understood and chosen behaviours.

The power of this approach is that it transcends generations.

It allows organisations—especially multi-generational ones—to navigate inevitable change not by enforcing alignment, but by creating it through listening.

Listening to one another’s:

• hopes

• needs

• perspectives

• and yes… wants

More than that, it is empowering.

It signals trust first.

It says:

“I trust you to do the right thing.
So I won’t burden you with layers of control to ensure it.”

And in doing so, it creates the conditions for people to bring their best.

Not just their technical expertise—but their imagination, creativity, and judgment.

Yet in most organisations, trust is something we talk about more than we practice.

Instead, we focus on what goes wrong.

We build rules around failure.

We create layers of control to prevent recurrence.

Entire functions emerge to monitor, enforce, and contain.

The unintended consequence?

People spend more time navigating the system than doing meaningful work.

And to regain efficiency, they begin to look for exceptions. Workarounds. Shortcuts.

Not out of malice—but necessity.

Which, in turn, leads to more rules.

And so, the loop tightens.

Now, consider a different approach.

Start by asking:

What is already working?

Bring people together to identify it.

Understand why it works.

Then elevate those patterns into shared principles.

Not imposed—but co-created.

Not enforced—but lived.

These principles become the guiderails.

The space within which people agree to operate.

The conditions within which trust can grow.

And when those conditions are right:

People don’t need to be controlled.

They choose to contribute.

They experiment.

They make mistakes.

And importantly—
those mistakes are not just tolerated, but celebrated
(as long as people remain safe)

Because that is where learning happens.
And where innovation actually begins.

This is how we begin to break the cycle.

Not by tightening the system further—
but by loosening it, intentionally.

And perhaps most importantly:

This is how we reduce the bias we bring as leaders, as designers, as consultants.

Not by trying to eliminate it—
but by creating space for others to shape the system with us.

Across generations.
Across perspectives.
Toward something shared.

Finding the Pony… and Learning to See the Herd

There’s an old idea I’ve come back to often:

Somewhere in every pile, there’s a pony.

It’s a simple metaphor—but it points to something much deeper in how we see the world, and how we lead within it.

What We’ve Been Trained to See

As humans, we are not neutral observers.

We are wired—deeply—for survival.

We scan for:

• risk

• threat

• gaps

• what’s missing

• what could go wrong

This is not a flaw.

It’s an ancient intelligence that has kept us alive.

But in modern organisations, this same instinct—left unexamined—becomes distorted.

It shows up as:

• constant problem-seeking

• over-correction

• tightening control

• reactive rule-making

We become highly skilled at identifying what isn’t working.

And in doing so, we unintentionally blind ourselves to what is.

From Finding Problems to Finding Potential

In a recent experience working with a group of young people, I found myself returning to this idea—but seeing it differently.

At first, like many leaders, I was attuned to:

• where guidance was needed

• where structure could be improved

• where things weren’t aligning

But something shifted.

Instead of continuing to search for the “next issue,” I made a conscious effort to look for what was already working.

Not superficially.

But deeply.

And what I found wasn’t a single “pony.”

It was a herd.

What Was Already There

The more closely I looked, the more I saw:

• initiative being taken without prompting

• collaboration emerging naturally

• creative problem-solving in real time

• care for one another embedded in action

Not perfectly.

But consistently.

And importantly—without being forced.

Creating Conditions, Not Control

This didn’t happen by accident.

From the beginning, the environment was shaped intentionally:

• clear guiderails instead of rigid rules

• shared ownership instead of top-down instruction

• space to experiment within safe boundaries

The expectations were understood.

But within those expectations, there was freedom.

And that freedom mattered.

Because it allowed something essential to emerge:

👉 self-managed leadership

Retraining the Survival Instinct

This is where the deeper shift lies.

Left on its own, the human mind will default to:

“What’s wrong here?”

But leadership—especially in complex human systems—requires a different question:

“What’s working here, and how do we do more of it?”

This is not ignoring problems.

It is rebalancing attention.

It is retraining ourselves to:

• recognise strength

• amplify positive patterns

• create environments where those patterns can expand

Because what we focus on does not just reflect reality.

It shapes it.

The Role of Mistakes

In this environment, something else became clear:

Mistakes were not interruptions to progress.

They were part of it.

When the guiderails are clear—especially around safety—mistakes become:

• data

• learning

• momentum

Not something to punish.

But something to understand.

And sometimes, even something to celebrate.

Because each mistake—met with reflection instead of reaction—builds capacity.

What Emerges When Conditions Are Right

When people are placed in the right conditions:

They do not need to be pushed.

They choose to show up.

And when they choose to show up:

• ownership increases

• creativity expands

• resilience strengthens

• leadership emerges

Not as a role assigned.

But as a natural expression.

From Ponies to Leaders

What I witnessed was not just participation.

It was transformation.

Young people growing into:

• imaginative thinkers

• capable problem-solvers

• emotionally aware collaborators

In other words—

👉 leaders

Not because they were directed into it.

But because the conditions allowed it.

A Different Way Forward

If we step back, the implication is significant.

In many organisations, we are still operating from a model of:

• guarding against failure

• controlling behaviour

• correcting deviations

But what if the path forward is not more control?

What if it is:

• clearer direction

• intentional guiderails

• shared ownership

• and a conscious shift in what we choose to see

The Real Work

The real work is not just in changing systems.

It is in changing attention.

It is in retraining ourselves—individually and collectively—to:

👉 see what is working
👉 support it
👉 and allow it to grow

Because when we do:

We don’t just find the pony.

We realise it was never alone.

From Guarding to Guiding: Reclaiming Flow in Organisations

When did organisations shift from guiding behaviour to guarding against it?

We’ve seen the consequences for decades. From corporate scandals like Enron and WorldCom to the quieter, everyday workarounds inside modern organisations—loopholes in expense claims, overtime structures, or policy interpretation. Different scale, same pattern.

An individual identifies an opportunity that fits within the letter of the rules, but not their spirit.

At some point, the system notices.

An audit. A review. A concerned supervisor.

Policies are pulled. Procedures examined. People interviewed.

And almost inevitably—ambiguity emerges.

So we do what organisations have been conditioned to do:

We write a new rule.

The Hidden Shift

This is where something subtle—but profound—has happened.

Rules are no longer created to guide behaviour toward a shared goal.
They are created to guard against undesired behaviour.

Over time, layers of these rules accumulate. And with each new layer, complexity increases. Contradictions emerge. And within contradiction lies opportunity—for exploitation.

Behaviour adapts accordingly.

Not: How do I contribute to where we are going?
But: How do I work the system?

This is not a failure of people.

It is a predictable expression of human survival instinct.

When the environment signals constraint and enforcement, the mind shifts toward optimisation and self-preservation.

The Guarding Trap

The more we guard, the more energy is required to maintain control.

More rules.
More oversight.
More enforcement.

And yet, the outcomes drift further from intention.

Because the system is no longer aligned with flow—it is resisting it.

A Different Approach: Guiding Frameworks

What if, instead of reacting with more rules, we redesigned the environment itself?

In my experience, the shift begins with:

• Clear, meaningful direction

• Shared understanding of purpose

• Frameworks that guide rather than constrain

Not rigid prescriptions—but intentional boundaries that allow movement.

This is harder to implement at first.

In organisations conditioned by control, the absence of rigid rules can feel like risk.

But something powerful happens when people begin to understand the why, not just the what.

Energy shifts.

Ownership increases.

Alignment emerges.

Flow Over Control

A river cannot be controlled.

Water will always find its path—over, around, or through any obstacle.

Organisations are no different.

The goal is not to control the flow.

It is to shape the conditions through which it moves.

To build gentle structures—guiding contours—that channel energy without constraining it.

When this happens:

• Less effort is required to sustain momentum

• Behaviour aligns naturally with purpose

• Progress accelerates

Returning to What Works

The organisations we remember most positively are not the most controlled.

They are the ones where:

• Direction was clear

• Trust was present

• Movement felt natural

We cannot return to the past.

But we can carry forward what worked.

In the present moment, we have the opportunity to move from guarding to guiding.

To replace control with flow.

And to build organisations that people don’t just comply with—

But move within, naturally.

At the Heart of All Directions

Over the past two weeks I’ve shared one of my favourite stories — one a good friend, mentor, and executive coach once told me.

The story of finding the pony.

It’s a simple story, but a rich one. There are many lessons hidden inside it. One of the most powerful is this: you cannot change the nature of people.

Which raises an important question.

If we cannot change the nature of people, how do we lead?

For me, the answer begins with looking to nature itself.

The wisdom of the ancients — of the first peoples — is rightly called wisdom. Long before modern scientific methods, the ancients developed their own way of understanding the world: through careful observation of patterns over long periods of time.

Nature was their teacher.

Recently I’ve had the time to reflect on one such teaching that many Indigenous traditions still rely upon today: the teachings of the four directions.

What I have come to realise is that at the heart of these teachings lies a simple but profound idea:

presence.

And presence, I believe, is the key to working with the nature of people rather than trying to change it.

The four directions offer a way of understanding life through the movement of the natural world.

The east, where the sun rises, represents spring — rebirth, renewal, and the dawn of something new.

The south, where the warm summer sun sits high in the sky, represents comfort, vitality, and the warmth of growth.

The west, where the sun sets, represents autumn — the end of the day, when the earth prepares for rest.

And the north represents winter — a time of reflection, when the land sleeps and we learn from the lessons the year has given us.

These teachings come from the northern hemisphere and are particularly rooted in the traditional territories of Indigenous peoples in what settlers now call Canada. But the underlying insight is universal.

They form a simple — yet elegant — way of understanding cycles.

What struck me most as I reflected on the four directions is that they are arranged in a circle.

At first I thought about how each direction connects to the others.

To begin something new in the east, we must leave something behind in the west.
The lessons of the past live in the north.
And when things go well, we eventually experience the warmth and comfort of the south.

But something else caught my attention.

The west and the north are rooted in the past.
The east and the south point toward the future.

None of the directions speak directly to the present.

And that is where the circle becomes important.

The circle represents continuity. Life moving endlessly forward.

An individual life may end, but life itself continues.

But the circle also has another property — one that I’ll explain imperfectly, and with apologies to the mathematicians and physicists who may find my explanation overly simple.

If you imagine the infinite points that make up the edge of a circle and then combine them, they converge toward the centre.

The heart of the circle.

And that centre point is zero.

It is the place where all directions meet.

That centre is the present.

The past lives behind us in the west and north.
The future emerges before us in the east and south.

But leadership — real leadership — happens in the centre.

In the present.

We leave the past behind, even as we carry its lessons.
We move toward the dawn of something new.
We work toward the warmth and comfort that success may eventually bring.

But we do all of that here and now.

In the present moment.

And this brings us back to the nature of people.

If we accept that we cannot change people’s nature — that optimism, scepticism, independence, caution, and curiosity are all part of the wiring people bring with them — then leadership is not about trying to reshape that nature.

Leadership is about being present enough to work with it.

To see people as they are.

To create conditions where their nature becomes contribution rather than friction.

Which brings me back to the story of finding the pony.

Sometimes we find ourselves staring at a very large pile of manure.

But the work of leadership is not to change who people are.

It is to remain present.

To see clearly.

And to continue the search — here and now — knowing that somewhere in the pile there may indeed be a pony.

When Control Replaces Clarity

We have a problem.

Let’s investigate it.

What are the root causes?
What rules were in place?
Which rules were broken?
Why were they broken?

What additional rules do we now need to prevent this from happening again?

Sound familiar?

Even in the best, most human-centred systems — including those grounded in Just Culture — more rules are nearly always among the recommendations that follow an investigation.

And in some contexts, that makes perfect sense.

In aviation, for example, safety engineering has saved countless lives. The well-known “Swiss cheese” model explains it clearly: one protective layer may have holes, but when you stack multiple layers behind it, the odds of a catastrophic failure decrease dramatically.

When you’re trying to prevent an aircraft from falling from the sky, layering safeguards is wisdom.

The trouble is not the model.

The trouble is that we have quietly applied it everywhere.

In everyday organisational life, every misstep invites a new layer.
A new policy.
A new approval step.
A new reporting requirement.

Individually, each one feels reasonable. Collectively, they form dense systems of control.

And control has a peculiar effect.

It creates a false sense of security.
And once introduced, it tends to require more of itself.

Over time, leaders stop sensing reality directly. They begin relying on procedure, language, dashboards, and structure to tell them what is true.

When sensing is replaced by structure, judgment slowly recedes.

And when judgment recedes, more control feels necessary.

This is where the chicken-and-egg question appears.

Do people need rules because they are untrustworthy?
Or do layers of rules slowly teach people that trust is unnecessary because the system will catch everything?

In my experience, most people come to work wanting to do a good job. It is rare that someone sets out to sabotage the organisation — and even when they do, there is usually a story behind it.

Yet as control accumulates, something shifts.

Responsibility becomes compliance.
Judgment becomes procedure.
Fear quietly replaces trust.

The most capable people — the independent thinkers, the ones hired for their edge — are asked to align. To soften. To fit the existing structure.

We celebrate independent heroes in hindsight. But in real time, independence inside organisations is often labelled rogue.

Contained. Managed. Redirected “for the good of the team.”

There is a simple story about two brothers.

One sees only flaws.
The other, faced with a pile of manure, assumes there must be a pony in there somewhere.

The story is often told as a lesson about optimism versus pessimism.

But that’s only one possible reading.

It can be about orientation.
About framing.
About how two people can stand in front of the same reality and experience entirely different worlds.

It can be about nature — the parts of us that do not shift easily, no matter how many policies are layered around them.

It can be about possibility — the instinct to search for something alive even when conditions appear unpleasant.

It can even be about systems — about what happens when environments are designed to suppress certain responses rather than channel them.

The point is not to extract a single moral.

The point is that people do not arrive as blank slates.

They arrive wired. Shaped. Inclined.

Leadership is less about changing that wiring than it is about deciding what kind of environment that wiring enters.

When layered control suppresses difference, teams may look aligned — but they become smaller. Quieter. Less alive.

If optimism is forced, it becomes naïve.
If scepticism is suppressed, it becomes resentment.
If independence is punished, it becomes withdrawal.

But when different orientations are allowed to exist — and are held within clear, thoughtful structure — something else happens.

Energy becomes contribution rather than friction.

Debate strengthens rather than fractures.

People leave conversations with dignity intact rather than ego bruised.

Over centuries, rules emerged to help tribes survive. Norms followed. Definitions of “normal” hardened.

Today, most of us live and work inside overlapping systems of control that were built to solve real problems at one point in time.

Individually, they made sense.

Collectively, they can constrain liberty more than we realise.

Most organisations are not trying to prevent aircraft from falling from the sky. They are trying to build, create, serve, and imagine.

And for that kind of work, dense stacks of control often do more harm than good.

What is usually absent is trust.

Trust that people will do the right thing simply because it is the right thing to do.

One definition of integrity that has stayed with me over the years is this: integrity is doing the right thing even — or especially — when no one is watching.

Layered control assumes the opposite.

There is a quieter way.

Not chaos.
Not the absence of leadership.
Not the removal of all structure.

But the careful reshaping of structure.

Clear guiderails instead of tight constraints.
Conditions that support judgment rather than replace it.
Space for independence without dissolving collaboration.

When people are trusted to bring themselves fully — optimistic, sceptical, independent, cautious — something shifts.

Responsibility replaces compliance.
Fear recedes.
Care increases.

Freedom, when properly held, does not create disorder.

It creates dignity.

And dignity produces care.

Leadership, in the end, is not about eliminating every pile of manure.

It is about building systems where someone is still free to look for the pony.

Quietly.