How to Pressure Test Your Own Strategy

April 23, 2026

Every CEO should pressure test their strategy quarterly. Most don’t. Here are five questions I use. If you can’t answer them cleanly, your strategy has holes.

1. What would have to be true for this to work?

List the assumptions. Market growth. Customer retention. Pricing. Win rates. Now rate each assumption from 1-10 on how certain you are. If your strategy depends on three assumptions at 6 or below, it’s fragile.

2. What’s our unfair advantage?

Not what makes you different. What makes you unfairly better than the competition at something that customers will pay a premium for. If you can’t name it in one sentence, you don’t have one.

3. Who are we intentionally not serving?

A strategy without a no-list is a wish list. The companies I’ve coached that accelerated growth did so by cutting the bottom third of their customers and doubling down on the top third. That’s strategy.

4. What are we doing that the market doesn’t value?

Every middle market company has legacy activities no one bought you for. Audit the last quarter. What did you spend time on that no customer ever paid for? That’s your cut list.

5. If we had to cut 30% of costs and grow 20%, what would we do?

I use this question with every CEO I coach. The answers are always revealing. The things you’d do in that scenario are usually the things you should be doing anyway.

Ready for a direct conversation about your business?

Bill Canady takes a limited number of strategy coaching calls each month with middle market CEOs, founders, and owners who want a direct read on where their company stands and what to do next. No pitch. No fluff. One honest conversation about growth, profitability, and exit readiness. Book your strategy coaching call at billcanady.com.

About the Author

Bill Canady

Bill Canady is a national best-selling author, Founder & CEO of The 80/20 Institute, and a global business leader known for transforming companies into high-performing, profitable enterprises. Over the course of his career, Bill has led multibillion-dollar organizations through their most critical challenges—navigating complex regulatory, investor, and media environments—while consistently delivering profitable growth.

Drawing on decades of executive experience, Bill created the Profitable Growth Operating System (PGOS), a proven framework designed to help leaders cut complexity, focus on the critical few, and accelerate growth. Through The 80/20 Institute, he and his team partner with CEOs, executives, and entrepreneurs worldwide to apply the 80/20 methodology in real-world settings, unlocking revenue growth, margin expansion, and shareholder value.

As both an operator and advisor, Bill’s mission is clear: to give leaders the tools, systems, and confidence they need to achieve sustainable, profitable growth — without sacrificing focus, culture, or execution.

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