#Strategy #Playbook

Strategy often gets romanticized. People imagine it’s about having a bold vision or spotting a brilliant insight no one else sees. But real strategy isn’t guesswork—or magic. Good strategy is about making clear, deliberate choices—and then asking:

"What must be true for these choices to work?"

This mindset shifts strategy from a creative brainstorm to a rigorous, testable discipline—and it’s just as essential for small businesses as it is for large corporations.

“Big decisions don’t need big budgets—they need clear thinking.”

Strategy is About Choices

Strategy isn’t about predicting the future. It’s about answering a specific question:

“What would have to be true for this option to be the best choice?”

This is radically different from asking, “What will happen?” It moves the focus from passive forecasting to active decision-making.  Whether you're considering entering a new market, launching a new product, or changing your pricing model—strategy is about choosing among possibilities. But not based on what’s most familiar or comfortable. It’s about which path gives you the best chance to win—and why.

The 5-Step Process

Here's a process to make strategy development scientific and structured:

1. Frame the Choice

Convert the issue into options.

Issue: Growth has stagnated.

Options:

a) Expand into new markets

b) Revamp the business model

c) Implement a different pricing model

2. Generate Strategic Possibilities

Don’t settle for the obvious options. Explore creative, even unconventional ideas.

3. Identify Conditions for Success

For each option, ask: What must be true for this to work well?

These are the key assumptions your strategy depends on.

4. Identify the Barrier Conditions

Which of those “must-be-true” assumptions are the least certain? The riskiest? These are the barriers you need to test.

5. Design Valid Tests

Instead of gambling, create simple, real-world tests that explore your assumptions before you fully commit.

Think: pilot programs, prototype offers, customer interviews, or pre-launch campaigns.

A Practical Example

Let’s say you’re thinking about offering a subscription model for your consulting services.

1. Frame the choice:
Stay with project-based billing or shift to monthly retainers?

2. Generate possibilities:
You could offer tiered monthly packages, pay-as-you-go support, or hybrid models.

3. Identify Conditions for success

What must be true?

a) clients must value ongoing support

b) be willing to pay monthly

c) not expect too much time for too little money

4. Barrier assumptions:
Will enough clients actually switch? Will it remain profitable at scale?

5. Test it:
Offer a limited-time monthly support plan to 3 trusted clients and measure satisfaction, usage, and profitability.

“Growth requires risk, but the best leaders validate before they commit.”

Common Missteps This Process Helps You Avoid

• Falling in love with one idea without exploring better ones
• Relying on gut instinct alone in high-stakes decisions
• Skipping testing because it feels like you “already know”

The most dangerous strategies aren’t the boldest—they’re the ones built on untested assumptions.

Key Takeaway

Great strategy isn’t about forecasting what’s going to happen—it’s about choosing thoughtfully and testing thoughtfully.

As a small business owner, you don’t need perfect foresight. What you need is the discipline to ask: What must be true? and the courage to test those truths. So next time you face a big decision—don’t just plan. Frame, test, and learn.

“The true power of strategy lies in its ability to simplify.”

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Our Insights

Our #Fundamentals series explains the essential “what” behind core business concepts. Each post is designed to give small and growing businesses a clear, jargon-free understanding of strategic, financial, and operational foundations — the building blocks every entrepreneur needs to lead with clarity and confidence.

Our #Playbook series is all about “how” to get things done. The Playbook details the practical steps, tools, and tactics needed to put those ideas into action. From building your first business model to improving cash flow or streamlining operations, this series gives you real-world strategies you can apply today — no jargon, just clarity.

Our #Deep-Dive series explores the "why" and "what if" behind business decisions — offering in-depth analysis, frameworks, case studies, and advanced insights. Here we break down:

The reasoning behind best practices

The trade-offs of strategic choices

What happens when things go right — or wrong

Complex scenarios, modeled or unpacked in detail

Think of it as the executive-level perspective — helping readers think critically, challenge assumptions, and make smarter, context-driven decisions.