Planning vs Strategy: Why CEOs Confuse the Two – and Why It Matters

Ask the leadership team of an organisation if they have a clear strategy, and almost all hands shoot up. Certainly initially.  Ask those same leaders to describe that strategy in just a few sentences – and you’ll the hands perhaps waver, or simply start to lower.

What most organisations call ‘strategy’ is often just a plan. A longer term plan. Possibly quite an elaborate plan! Useful, perhaps. Comforting, certainly. But strategy? Not quite.

The difference matters – not just for consultants, advisors and the PowerPoint brigade, but for every CEO who wants their business to grow, adapt, and succeed sustainably. Because confusing planning with strategy doesn’t just slow progress; it risks taking your business confidently in the wrong direction, or on a slow bleed to irrelevance.

The Comfort of a Plan 

Let’s be honest: planning feels good. It gives us control, structure, and the satisfying illusion that the world will cooperate with our spreadsheets and to-do lists. Good planning reduces anxiety. It turns goals into neat milestones, makes teams feel busy and productive, and reassures investors that things are under control.

The problem?

The world rarely behaves according to plan. Markets shift, competitors move faster than expected, suppliers make a shock announcement. The assumptions that underpin our carefully crafted slide decks begin to crumble. Or more accurately, surface and crystalise right in front of our eyes. That’s when leaders realise that being organised isn’t the same as being strategic.

The Uneasy Nature of Strategy 

Strategy, by contrast, is uncomfortable. It asks hard questions, forces tough choices – often with limited information, and thrives in uncertainty. It doesn’t provide immediate reassurance; it provides direction and positioning. Good strategy connects intentions to outcomes. It answers why we’re doing something, where we’ll focus our energy, and how we’ll win – not what we’ll do on Monday morning.

A useful distinction:

Planning asks, What next?

Strategy asks, What if?

Plans seek control. Strategy seeks advantage. One is linear and logical; the other is adaptive, creative, and often a little messy. Plans deliver efficiency. Strategy delivers differentiation.

Michael Porter famously defined strategy as “making choices, trade-offs; deliberately choosing a different set of activities to deliver a unique mix of value.” That act of choice – and saying no as much as yes – is what distinguishes a strategist from a planner.

It’s why I love facilitating (tough) strategic conversations. And keeping the questions simple. What are we NOT doing – or not doing yet – remains one of the hardest questions for a leadership team to answer as one.

When Founders Get It Right (and Wrong) 

Consider Airbnb’s early days. In 2008, the founders were broke. To keep the business alive, they sold novelty cereal boxes (‘Obama O’s’ and ‘Cap’n McCain’s’) during the U.S. election. A tactical move? Certainly. But it was part of a broader strategic intent: to test whether people would buy into an idea – any idea – built around shared experiences and personal connection. Their near-term hustle bought them time to execute their long-term strategy. When they later joined Y Combinator, Paul Graham famously remarked, “If you can convince people to pay $40 for $4 boxes of cereal, maybe you can convince strangers to live together.” The rest is history.

Contrast that with the countless organisations whose ‘strategies’ are simply rebranded operational plans: a list of initiatives, KPIs, and cost targets. These teams work hard, but often in service of yesterday’s logic. Targets taken from last year – and extrapolated forwards. Sound familiar? They’re busy, but not moving forward.

Why We Confuse Planning with Strategy 

Part of the confusion lies in human nature. The human brain likes – and seeks – certainty. For many, it finds comfort in our lists, milestones, and meetings. Planning rewards the same neural pathways as ticking off a to-do list – a small dopamine hit every time something gets done. (Which is why many people admit to writing things on their to do list that are already finished!).

Strategy demands the opposite. It requires holding paradoxes, exploring ambiguity, and tolerating anxiety, all of which our brains instinctively resist.

That’s also why, in project briefs and workshops, I often see leadership teams rush to ‘the plan’ – “what are we actually going to DO!” – before they’ve even discussed the strategic issue that they’re collectively solving.

As I often remind clients: a beautifully executed plan built on a poor strategy simply gets you to the wrong place faster.

A Simple Test 

Here’s a quick test I use with boards and leadership teams.

Ask someone to describe your strategy. If their explanation immediately triggers the question “How?”, you don’t have a strategy — you have a plan.

Good strategy identifies the critical challenge standing between you and your ambition, sets out a guiding policy for overcoming it, and defines a coherent set of actions to make it happen. That’s not a to-do list — that’s a system of meaning.

The Choice Cascade 

Roger Martin and A.G. Lafley, in Playing to Win, proposed a simple but powerful cascade of strategic questions:

What is our winning aspiration?

Where will we play?

How will we win?

You might simply pause here and reflect on how easily you can answer those questions for your own organisation? And if you asked all your colleagues to write down their answers blind of each other, how confident are you that they would provide the same answers?

Now continue:

What capabilities must we have?

What management systems will support them?

Most “strategic plans” jump straight to questions four and five. True strategy starts at one. As Martin also argues, the most important question in strategy is not “what’s true?” – which he describes as ‘adversarial position taking’ but “What would have to be true?” That subtle shift — from arguing opinions to exploring possibilities — surfaces our assumptions, and turns conflict into creativity and collaboration.

Strategy as a Human Practice 

In Be More Strategic, I describe strategy not as a document, but as a discipline – a mindset, a way of seeing and deciding. Strategy is human. It lives in conversations, decisions, and choices often under pressure, with limited information.

Which means the quality of your strategy is inseparable from the quality of your thinking and the self-awareness of the people making the calls.

I know from first-hand experience, having worked with thousands of people all over the world, that great strategists, whether in business, sport, or the military, share a few habits in common:

• They make space to think.
• They listen deeply, not just to words, but to silence, intent, and contradiction.
• They are comfortable with uncertainty. They even seek it.
• They’re decisive, but not reckless.
• They balance logic and intuition.
• They learn fast, and act faster.

In my work with senior leaders, I’ve found that those who pause to reflect, even briefly, make better strategic decisions than those who rush to action. Being strategic isn’t about being slow; it’s about being deliberate, being intentional, being considered.

Breaking free of busyness  

Many CEOs describe themselves as “too busy.” But busy in service of what? If you find yourself firefighting every week, there’s a good chance you’re planning hard but strategising little. A good strategy should liberate you from constant reaction. It should simplify, clarify, and align. It should give people permission to stop doing things that don’t matter and confidence to double down on those that do.

When I work with executive teams, I often find that simply distinguishing strategy from planning unlocks a wave of creativity and relief. The best ideas come not from adding more to the list, but from deciding what not to do.

Strategy Is a Superpower — and It’s Learnable 

Being strategic is not a skill reserved for the elite, for the best consultants or those with MBAs. It’s learnable. It starts with self-awareness – knowing your biases, triggers, and blind spots – and builds through curiosity, listening, critical thinking, creativity, and decisive action. Those are some of the twelve practices I describe in the Strategic Mastery Framework, the backbone of my work.

The key insight: strategy begins with how we think, not what we know. Plans change; mindsets endure. Focus on what you notice, not what you know. ask better questions, rather than providing better answers.

Practical Next Steps for Leaders 

If you want to ensure you’re leading strategically — not just operationally — start here:

Clarify the ambition. What’s the “win” you’re really playing for?

Name the challenge. What’s the obstacle in your way?

Set out your options. Make the hard choices. Strategy is as much about exclusion as inclusion.

Connect intentions to outcomes. Ask how every major initiative contributes to your guiding policy.

Create space to think. Protect time for reflection. It’s not a luxury; it’s leadership.

The CEO’s Role 

The role of the CEO is not to have all the answers — it’s to create the conditions for good strategy to emerge. That means modelling curiosity, rewarding candour, and inviting diverse perspectives into the room. It also means resisting the urge to jump straight to execution.

Strategy is everyone’s business — but it must start with leadership that values thinking as much as doing.

The next time you’re tempted to call a meeting to “review the strategic plan,” pause and ask yourself: are we discussing the plan or the strategy? The former will keep you organised. The latter will keep you relevant.

In uncertain times, the CEOs who will thrive are not those with the neatest plans, but those with the clearest strategies – leaders willing to make hard choices, see the big picture, and think beyond the next quarter.

That’s not just good business. It’s good leadership.

Written by Charlie Curson. Have you read?
World’s Richest Royals. Global Financial Centres Index.
Richest Countries. World’s Richest People (Billionaires).
The Chief Economists magazine, UGGP News, and the CEO Policy Institute.