🎯 Misplaced Shoulds in Strategy: Why Reality Beats Ideals Every Time

🔍 The Trap of “Should” Thinking in Strategy

Too often, business leaders approach strategy with the same mindset they’d apply to a checklist — looking for a definitive answer to how things should be done. Questions like “Should we have a single strategy cascade or several?”, “Should startups do strategy or just execute?”, or “How often should we review our strategy?” pop up frequently.

But here’s the truth: there’s no universal “should” when it comes to strategy. No perfect frequency. No golden rule about number of cascades. And certainly no one-size-fits-all template that neatly applies to every business at every stage.

What really matters is starting from the reality of your situation — not an idealized abstraction of how strategy ought to be.

🧭 Strategy Already Exists — Whether You Name It or Not

Many executives fall into the trap of believing strategy only exists if they consciously create it. But in reality, every organization already has a strategy, even if it’s informal, fragmented, or unspoken.

Your company makes choices every day: where to focus, how to compete, what capabilities to build. These decisions define your de facto strategy. Whether you document it or not, your business has a Where-to-Play (WTP) and a How-to-Win (HTW). Even startups — often considered too fast-paced for strategic exercises — are constantly making consequential choices that shape their strategy from day one.

The real challenge isn’t creating strategy from scratch — it’s recognizing the one that already exists, making sense of it, and improving it where necessary.

🛠 The Only “Should” That Matters: Start with Reality

Let’s go back to the reader’s question about cascading strategy across one corporation and four business units. Should he do five cascades? One? Three?

The answer lies in the actual strategic alignment between the units. The reader needs to reverse-engineer the current strategies using the strategy choice cascade as a tool. If the strategic intents, capabilities, and competitive positioning of all units are aligned, one cascade might be enough.

Take a (fictional) example of a food company with three divisions: pasta, pasta sauce, and parmesan cheese. If all three divisions share the same aspiration — say, becoming the premium natural choice in their category — and follow similar paths to market, a single cascade might suffice.

But what if the parmesan cheese business operates in a different supply chain, faces distinct competitors, and targets a different customer base? In that case, forcing it to fit into the corporate cascade would hinder its success. That unit would need its own cascade — because reality demands it.

🧠 Fast-Moving Doesn’t Mean Strategy-Free

Some leaders claim their environment is too fast-changing to pause for strategy. But speed doesn’t erase the presence of strategy — it just makes it harder to spot. Even in rapid environments, choices are still made. Those choices still amount to a strategy. Ignoring or avoiding the strategic implications doesn’t make them disappear — it only weakens your ability to steer the business.

Instead, reverse-engineer what’s really happening, then evaluate: Are your current outcomes aligned with your goals? If yes, continue. If not, don’t wait for the next quarterly offsite — make new choices now.

📅 How Often Should Strategy Be Reviewed?

Here’s another recurring question: “How often should we revisit our strategy?”

Once again, the answer depends on outcomes. Strategy is not a calendar event — it’s the pattern of your choices. If those choices are driving results you’re happy with, there’s no rush to change them. But if they’re not delivering what you want, it’s time to reassess — no matter when your last review was.

There’s no magic number of months or years. There’s only a need for clarity, alignment, and performance. That’s your signal.

🧩 Strategy Is What You Do — Not What You Say

At the end of the day, strategy isn’t about crafting perfect mission statements or polished PowerPoint decks. It’s about making deliberate, consistent choices in pursuit of a meaningful aspiration.

Don’t let misplaced shoulds steer you toward abstractions. Instead, start with what your business is actually doing. Understand it. Question it. Then improve it — or keep it, if it’s working. The only rule that matters? Be grounded in reality.