The real work of leadership is not forecasting the future but building teams and cultures that are ready to meet it.
“Plan for order and you’ll be destroyed by chaos. Prepare for chaos and you’ll thrive in any condition.” — Sahil Bloom
I planned the first 25 years of my life with precision: get good grades, go to law school, work for a judge, and land at a top-tier law firm.
I ticked every box—and yet, once I “arrived,” I was met with a confronting realisation: I didn’t want to be a lawyer.
There was no version of the plan that accounted for that. I’d mapped the terrain meticulously but hadn’t done the deeper work of preparing for who I was becoming—or what I’d need when the plan no longer fit.
That moment shaped how I lead today and how I support others to lead through change.
Planning isn’t enough anymore
In leadership, we talk a lot about strategic planning—roadmaps, milestones, OKRs, five-year plans. These are useful, but they’re only half the equation.
Today’s environment is anything but predictable. Technology is evolving fast. Economic uncertainty is constant. Careers are no longer linear. The best-laid plans are often outdated within weeks, yet many leaders still treat planning as their primary tool.
According to the World Economic Forum’s Future of Jobs Report 2025, the number one skill we need to thrive is adaptability. That’s where preparation comes in.
Planning vs. preparation: what’s the difference?
The two concepts are often conflated, but they serve different purposes.
Planning is about creating a roadmap. It assumes control and predictability, and answers the question: “What should we do?”
Preparation is about building readiness. It assumes the unexpected will happen—and equips you with the mindset, skills, and systems to adapt. It asks: “Who must we become to handle what’s coming?”
It’s the difference between having a plan and being able to shift gears when that plan no longer applies.
We’ve all lived that difference:
- Your product launch was locked in—until a competitor moved faster.
- Your strategy looked great—until a global pandemic changed the game.
During COVID, the gap between planning and preparation became impossible to ignore. Plans were scrapped overnight. The most adaptable leaders weren’t the ones with the slickest documents—they were the ones with resilient teams and prepared minds.
And it’s not just in crisis. This dynamic plays out every day:
- Going for a bushwalk? The plan is the trail map. Preparation is packing for rain and knowing how to navigate if you lose reception.
- Moving in with someone? The plan is who pays the bills. Preparation is knowing how to navigate tension when stress rises.
When to plan vs. when to prepare
Use this simple matrix to guide your approach to action:
| Predictable | Unpredictable | |
| High Stakes | Plan with contingencies | Prepare to pivot |
| Low Stakes | Plan for efficiency | Experiment, adapt, learn |
Planning still matters, especially when the path is clear and the margin for error is tight. It’s essential for operations, compliance, and areas where consistency counts.
But when you’re leading through complexity, ambiguity or rapid change—which is often the case—planning alone isn’t enough. In these moments, preparation is your edge. It’s what enables you to navigate uncertainty, adapt quickly, and move forward when the original plan becomes obsolete.
Yet most of us default to planning because it feels safe and structured. Preparation demands more: vulnerability, flexibility, and a willingness to face the unknown.
This is the real work of leadership—not forecasting the future, but building teams and cultures that are ready to meet it.
How to build your preparation muscles
Preparation isn’t just a mindset—it’s a skillset. And like any skill, it can be trained.
Here are five core muscles every leader needs to build:
1. Train for uncertainty
You can’t eliminate uncertainty, but you can expand your capacity within it.
How to build this muscle:
- Simulate the unfamiliar. Step into situations where you don’t have all the answers—lead a cross-functional project, facilitate without slides, or make a call with incomplete data.
- Stretch your discomfort tolerance. Sit with ambiguity longer before jumping to resolution. Check out Elizabeth Weingarten’s How to Fall in Love with Questions for practical tools to build this muscle.
- Debrief surprises. When something unexpected happens, ask: What caught me off guard? How did I respond? What would I change next time?
2. Think in scenarios, not scripts
Plans are useful, but they rarely survive first contact. Scenarios build flexibility.
How to build this muscle:
- Map three versions of the future. Outline optimistic, realistic, and disruptive outcomes. Ask: If this happens, then what?
- Use the two-way door test. Is this decision reversible? If yes, move fast. If not, slow down and stress-test it.
- Seek outside input. Invite perspectives beyond your team to shrink your blind spots.
3. Strengthen optionality
Optionality gives you room to pivot, breathe, and choose—especially under pressure.
How to build this muscle:
- Upskill across functions. Create redundancy in your team—and range in yourself.
- Invest in diverse relationships. Connect with people outside your bubble. Strong, varied networks create future pathways.
- Create breathing room. Leave financial, emotional, and time buffers so you’re not always maxed out.
4. Practise letting go
Holding on too tightly can block better options. Letting go builds trust and models adaptive leadership.
How to build this muscle:
- Call the pivot early. Don’t fake certainty. Explain the “why” clearly when shifting course.
- Run release audits. Ask: What are we holding onto that no longer serves us? Change your process in a team meeting. Reframe a goal you’re no longer energised by.
- Detach from ego. Just because it was your idea doesn’t mean it’s still the right one.
5. Reflect and realign regularly
Preparation isn’t a one-time act—it’s a habit.
How to build this muscle:
- Schedule monthly sense-checks. Ask: What’s changed? Are we solving the right problem or just the familiar one?
- Zoom out. Make space for regular reflection—not just action. You can’t lead strategically if you’re always in the weeds.
- Ask future-facing questions. What will your team need next quarter that they don’t need now? What needs to evolve in you?
Leadership for a new era
I still plan. But I prepare more. Because when I look back, the defining moments—the pivots, the unexpected turns—weren’t the ones I planned for. They were the ones that tested my readiness.
As a leader, your greatest power isn’t having the perfect plan. It’s building a mindset and culture that can thrive when the plan breaks.
Planning gives you structure.
Preparation gives you options.
Adaptability gives you staying power.
In a world where change is constant, preparation is no longer a nice-to-have. It’s your responsibility—as a leader and a human.
So ask yourself: Are you preparing for the future you expect—or the one you can’t yet see?
Because the future will favour the prepared.
May Samali is the Founder and CEO of Human Leadership Lab, a global leadership development company. As a speaker, facilitator, coach, researcher, investor and board director, May wears multiple hats to unlock leadership potential in organisations, teams and individuals.
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