Leadership Is an Art (and Why That Matters for Community Builders)

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Do you see yourself as a leader?

If you run a Skool community, or a household, you are already leading whether you use that word or not.

That’s why Leadership Is an Art by Max De Pree remains one of the most useful leadership books I’ve ever read, even decades later, and especially for online communities.

The at of leadership is "liberating people to do what is required of them in the most effective and humane way possible."

De Pree doesn’t treat leadership as a role or a strategy. He treats it as stewardship... a temporary

responsibility for people, culture, and direction.

That framing changes everything.

Community is not content. It’s a human system.

Most people approach communities like products.

Making more posts, prompts, or activity isn't leading.

The work of a leader is not to generate output. It’s to create the conditions where people want to contribute.

That includes:

Psychological safety
Clear expectations
Mutual respect
A sense that presence matters

When those conditions exist, participation follows naturally. When they don’t, no amount of “engagement hacks” will fix it.

💫 Covenant beats contract

One of De Pree’s strongest ideas is the difference between contracts and covenants.

Contracts are transactional.

Covenants are relational.

Most online communities are built on unspoken contracts:

I post, you respond
I pay, you deliver
I show up, I get value

WISE communities work better when they function as covenants:

We care how people experience this space
We protect dignity, diversity, equality, inclusion
We value contribution beyond metrics

That means being intentional about how people are treated, especially when they are new, uncertain or quietly lurking.

💫 The leader defines reality

This is one of De Pree’s most quoted ideas for a reason.

In a community, defining reality looks like:

Being authentic about sharing rather than posting filler

De Pree rejects performative leadership. Filler is false reality. Authentic sharing is reality.

Acknowledging confusion bor misalignment instead of pretending it isn’t there

His emphasis is on not allowing quiet distortion to persist. Pretending is the opposite of defining reality.

Saying “this isn’t working” and adjusting course as needed

A direct behavioral translation of stewardship over ego. De Pree consistently prioritizes correction over pride.

💫 Structure serves people, not the other way around

De Pree ran Herman Miller, a design company, and that influence shows. Structure matters, though only when it serves human behavior.

In Skool terms:

Categories should reflect how members actually think and talk
Events should respect attention and energy, not just calendars
Systems should make it easier to contribute, not harder

If your structure requires constant explanation, it’s not aligned with human use.

💫 Ending well matters

De Pree places unusual emphasis on endings.

In most communities, endings don’t happen. They dissolve.

A challenge runs for seven days and then the next thing appears.
A discussion gets traction and then slips down the feed.
An event happens and the recording is posted with no follow-up or insights

When no one says, “This is complete,” or “Here’s what came out of it,” or “Here’s who showed up and why that mattered” there can be a feeling of drift.

Digital spaces don’t signal closure the way in-person spaces do. There’s no room emptying out. No chairs stacking. No natural pause that signals, “We’re done for now.”

So unless a community leader creates that pause intentionally, things just trail off or ramble on.

When De Pree talks about endings, here's how it shows up in online communities in very practical ways:

A short closing post after a challenge that names focus and results.
A simple acknowledgment thread after an event that thanks specific people for showing up or contributing.
A recap that marks a phase as complete before moving on.

Those moments do a few important things at once. They help people orient themselves. They signal that participation is noticed. And they give the brain a sense of completion, which is what makes returning feel solid instead vague and draining.

People remember how things end. Closure opens the next door

That memory shapes how, and whether, they return.

🤓 What this means for WISE Skool Builders

Leadership in a Skool community isn’t about being the loudest voice or the most consistent poster.

It’s about: