You want your team to move fast. Stay creative. Adapt when things shift.
But here’s the problem: most founders swing between two extremes.
Over-structure: Lock everything down. Kill the spontaneity. Wonder why no one’s bringing ideas anymore.
Under-structure: Wing it. Hope something magical happens. Watch the team spin out because no one knows what they’re supposed to be doing.
Playfulness doesn’t thrive in either extreme. It doesn’t live in rigidity. But it doesn’t survive long in chaos either.
What it needs is something in the middle. The minimal viable structure.
What Bill O’Hanlon Taught Me About This
In Episode 2 of Being Playful, therapist and songwriter Bill O’Hanlon said something deceptively simple:
“I always master the structure. Then I play.”
At first, it sounds like “learn the rules before you break them.” But it’s not that.
It’s this: playfulness isn’t what happens despite structure. It’s what emerges from structure. The right-sized structure.
Bill talks about preparing his talks. He learns the shape. The key transitions. The opening and close. He doesn’t script every word. He gives himself a container.
That container becomes the confidence. And the confidence becomes the freedom.
Once it’s in place, he can improvise. Make a joke. Shift tone. Respond to the room. Not because he’s winging it. But because he’s held by something that allows him to let go.
Why This Matters When You’re Leading a Team
So many of us say we want more spontaneity. More openness. More innovation.
But in moments of stress (high stakes meetings, product sprints, sensitive strategy conversations), our nervous systems don’t crave freedom. They crave clarity.
Not rigidity. But something to lean on. Something to trust. A shared sense of rhythm.
If you skip the structure, people spin. If you lock it down too tightly, they shut down.
The sweet spot? A structure just strong enough to hold the room. And just light enough to invite something unexpected.
(This is where the PPM Method earns its keep. Pause, Play, Move. The pause is the structure. The play in the middle is where possibility lives. And it only works when it’s cradled on either side.)
Where You See This Pattern Everywhere
Jazz musicians don’t wait until they’re experts to improvise. They improvise within chord structures.
Kids don’t need total freedom to play. They use rules to create worlds.
And in leadership? The best strategic offsites, the best feedback sessions, the best pivots in crisis don’t happen because someone said “let’s be playful.” They happen because someone created the conditions where playfulness could emerge.
And often, that means starting with a minimal viable structure.
What This Actually Looks Like
This doesn’t mean you need everything figured out before you begin. That’s just perfectionism in disguise.
What it does mean is that playfulness is rarely chaotic. It’s often incredibly well-held. Invisible scaffolding is doing its job so well, you barely notice it. But it’s there.
For leaders, this is a shift in how we see our role.
Instead of asking “how do I control this?” or even “how do I lead this?”, try: What’s the lightest structure I can offer that makes play possible?
Sometimes that’s a thoughtful agenda with one open space.
Sometimes it’s a brainstorm with a clearly framed prompt.
Sometimes it’s just showing up with your own state regulated enough to let the team settle into their best.
The Bottom Line
Stop trying to choose between structure and spontaneity. You need both.
The structure is the kindness. The play is the gift. One makes the other possible.
So the next time you’re writing, creating, coaching, designing (or leading a room), don’t ask what you need to add to make it more playful.
Ask instead: What’s the minimal viable structure that will let playfulness find its way through?
Because when you get that part right, the rest often takes care of itself.
(And if you get it wrong, you’ll know. Everyone will either freeze up or flail around. Both are data.)