Here’s Why Improvising Works Better Than Planning

This expert opinion by Jeff DeGraff, author of Making Stone Soup: How to Jumpstart Innovation Teams, was originally published on Inc.com.

We’ve been taught to treat plans like lifelines—threaded through gantt charts, timelines, and mission statements. In business, as in war, we fetishize planning because it gives us the illusion of control. But what happens when the world doesn’t cooperate?

It’s not a hypothetical question. The world never cooperates.

If you’ve led a team through a product launch, a reorg, or a strategic pivot, you’ve likely discovered this yourself: the best-laid plans fall apart the moment they make contact with reality. Not because they’re bad plans—but because they’re built for yesterday’s conditions.

This isn’t an argument against planning. It’s a call to rethink what planning is for.

Uncertainty Isn’t The Exception—It’s The Environment

In my work with leaders across industries—and yes, militaries—I’ve seen the same mistake play out in boardrooms and battlefields: we treat uncertainty like a temporary disruption rather than a permanent condition.

We prepare with fixed frameworks and set-piece solutions. We plan for what will happen, not for how we’ll respond when it doesn’t.

But the best leaders don’t just make plans. They make teams that can adapt when the plans fall apart. They create conditions for improvisation, not just execution.

They know that leadership today is less like conducting an orchestra and more like playing in a jazz combo. Everyone has to listen. Everyone has to adjust. Everyone has to know when to solo—and when to stop.

The Mindset Shift: From Prediction To Preparation

This shift—from prediction to preparation—isn’t intuitive. Most of us were educated in systems that reward right answers, not adaptive thinking. We’re praised for being efficient, not for being experimental.

But efficiency is only useful when the path is known. In new terrain, it’s adaptability that matters most.

In military circles, this shows up in the concept of “mission command”—a decentralized approach that gives teams a clear objective but allows them to determine the best route in real time. It’s about building trust, not just process. Clarity of purpose, not rigidity of plan.

The same idea applies to business. We don’t need more rules for how to act. We need more readiness for how to adjust.

Control Is Not The Opposite Of Creativity

One of the great myths of leadership is that creativity and control are opposites. But the most creative organizations I’ve worked with—whether in defense, tech, or the arts—don’t reject discipline. They embed it strategically.

They build frameworks that support improvisation rather than stifle it. They clarify values, roles, and responsibilities so that when the moment demands deviation, people know how far—and in what direction—they can move.

This isn’t chaos. It’s intelligent elasticity.

It’s a way of building systems that flex under pressure rather than snap.

Train For The Pivot, Not Just The Plan

If you want agility in your organization, you have to design for it. Not in the strategy binder, but in the day-to-day behaviors you reward, the systems you use to learn, and the culture you actively shape.

In our innovation work with companies and military organizations alike, we use a principle borrowed from medical training: See one. Do one. Teach one. The idea is simple but profound. Real learning happens not just through instruction but through application and transmission. You don’t understand how to respond under pressure until you’ve done it. And you don’t truly integrate the lesson until you’ve helped someone else do it, too.

So we build that cycle into our teams. We simulate pressure. We throw in constraints. We change variables. Not because we want people to fail—but because we want them to practice adjusting when they do.

This is how you build adaptive capability into the muscle memory of your organization. It’s not about teaching people to follow the playbook. It’s about preparing them to write the next page when the playbook ends.

Resistance Is Just Data in Disguise

If you’re leading change, expect resistance. Not as a sign of failure—but as proof that you’re doing something that matters.

In fact, one of the worst signals a leader can get is unanimous agreement. It often means people aren’t fully engaging with the challenge—or worse, they don’t believe they have permission to. Creative friction, disagreement, even confusion—these are not dysfunctions. They’re diagnostics. They tell you where people are stuck, where systems are rigid, and where old assumptions need to be broken.

In other words, resistance isn’t an obstacle. It’s a form of feedback.

This mindset shift—from managing resistance to mining it—is what separates static organizations from adaptive ones.

Build the System Around the People—Not the Other Way Around

One of the most common traps I see in organizations is designing systems for idealized conditions and idealized workers. Everything works great—until the unexpected happens or the key person rotates out. Then the whole thing collapses.

That’s why the best organizations build resilience into their structure. They don’t just focus on the task. They focus on the network. On who can back up whom. On how information flows, how decisions are made, how authority is shared without being diluted.

In short: they treat people as the system.

And when you do that, you don’t lose your culture when someone leaves. You carry it forward—because it lives in relationships, rituals, and shared ways of working, not in org charts.

The New Planning Paradigm

We don’t need to stop planning. We need to start planning for the unplannable. For late-breaking news. For sideways turns. For customers who change their minds, and markets that rewrite the rules mid-game.

This means building leaders who can improvise with discipline. Teams that can shift without splintering. Cultures that can metabolize conflict instead of avoiding it.

In the end, the goal of leadership isn’t to prevent plans from breaking. It’s to get really good at what happens next.

Because the organizations that thrive won’t be the ones with the best plans.

They’ll be the ones with the best practices for when the plan breaks.