Playing to Win: How Strategy Really Works and Why Most Companies Fail at It

Playing to Win: How Strategy Really Works and Why Most Companies Fail at It

Strategy is a word that gets thrown around so much it basically means nothing anymore. You sit in a boardroom, someone pulls up a slide deck with fifty goals on it, and they call it a "strategic plan." It isn't. Most of the time, it's just a glorified to-do list or a set of pipe dreams disguised as ambition. If you’ve ever felt like your team is running a hundred miles an hour but getting nowhere, you’re likely seeing the difference between "initiatives" and actual strategy.

Real strategy is about choices. Specifically, it’s about making hard, sometimes painful trade-offs to win in a specific place. This is the core of playing to win: how strategy really works in the real world. It’s not about being the best at everything. It’s about being the only one who does this specific thing for this specific person.

If you can't say "no" to a profitable-looking opportunity because it doesn't fit your framework, you don't have a strategy. You have a wish list.

The Lafley and Martin Framework: It’s Not Just Theory

Back in the early 2000s, A.G. Lafley took over Procter & Gamble when the company was basically a mess. They were trying to do too much. Their stock was tanking. Lafley teamed up with Roger Martin, then the dean of the Rotman School of Management, to fix it. They eventually distilled their process into five choices. These aren't just steps; they are a reinforcing loop.

First, what is your winning aspiration? This isn't a mission statement like "we want to be the best." It’s a definition of what winning looks like in your specific sandbox. For Olay, it wasn’t just "selling more moisturizer." It was about dominating the "prestige" skin care market at a price point that made sense for mass-market retail.

Then comes the "Where to Play" choice. This is where most people mess up. They want to play everywhere. But if you're everywhere, you're nowhere. You have to pick geographies, product categories, and consumer segments. P&G decided to focus on the "mass-tige" segment—shorthand for prestige quality at mass prices. They intentionally walked away from certain demographics to win others.

Why "Best" Is a Trap

We're conditioned to want to be the best. But in business, "the best" is subjective. If you ask ten people what the "best" car is, you’ll get ten different answers ranging from a Ferrari to a Toyota Prius. Strategy isn't about being the best; it’s about being unique.

Michael Porter, the Harvard professor who basically invented modern strategy, has argued for decades that competition to be the best is a race to the bottom. If everyone is chasing the same "best" features, everyone ends up looking the same. Prices drop. Profits evaporate. Everyone loses.

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True strategy is about the "How to Win" part of the equation. This is your competitive advantage. It’s either a low-cost structure (think IKEA or Southwest Airlines) or differentiation (think Apple or Disney). You can't really do both. If you try to be the highest quality and the lowest price, you’ll probably just go broke.

I've seen so many startups try to "disrupt" an industry by promising everything to everyone. They want the premium branding of a boutique firm but the scale of a tech giant. It almost never works. They end up with a "middle-of-the-road" identity that doesn't resonate with anyone.

The Capabilities That Actually Matter

Once you know where you’re playing and how you’re winning, you need the "Must-Have Capabilities." This is the stuff you have to be world-class at. If your strategy is based on innovation, you better have the best R&D and a culture that tolerates failure. If your strategy is low cost, your supply chain management needs to be ruthless.

Look at Southwest Airlines. Their strategy is point-to-point, low-cost travel. To make that work, they needed a specific set of capabilities: fast gate turnarounds, a single type of aircraft (the Boeing 737) to simplify maintenance, and a culture that keeps employees productive and happy. If they started flying 747s for long-haul international flights, the whole system would break. Their "How to Win" would be compromised by a "Where to Play" expansion that didn't fit their capabilities.

Most companies have a list of twenty "core competencies." That’s nonsense. You can really only be "world-class" at maybe three or four things. Everything else just needs to be "good enough."

The Management Systems Nobody Talks About

The final piece of playing to win: how strategy really works is the management systems. These are the boring bits: the meetings, the KPIs, the budget cycles. But this is where strategy goes to die. If your strategy says you value long-term innovation but your bonus structure is based on quarterly sales, guess what your employees are going to focus on?

Exactly.

Strategy is often disconnected from the day-to-day. You need systems that reinforce the choices you've made. For a company like Netflix, that means a culture of "freedom and responsibility" that allows them to move faster than traditional studios. For a manufacturing firm, it might mean a rigorous Six Sigma process.

Strategy Is a Theory, Not a Fact

One of the most refreshing things Roger Martin says is that strategy is just a set of hypotheses. You're basically saying, "I bet if we do X and Y, customers will do Z."

You have to be willing to be wrong.

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The problem is that most corporate cultures treat strategy like a religious text. Once it's written, it's "the plan." But the market is a living, breathing thing. Competitors react. Technology changes. A good strategist is constantly looking for "validity markers"—signs that their theory is actually working in the real world. If the data says your "Where to Play" choice was a mistake, you pivot. You don't just keep digging the hole.

Common Strategy Myths

People often confuse strategy with vision. A vision is where you want to go. Strategy is the logic of how you’re going to get there.

Another big one: "Our strategy is to grow 20% this year."
That’s not a strategy. That’s a goal.
A strategy would be: "We will grow 20% by capturing the mid-market segment in Western Europe through a digital-first distribution model that undercuts traditional distributors by 15%."

See the difference? One is a wish. The other is a plan of attack.

Then there's the "Best Practices" trap. Copying what your competitors are doing isn't strategy. It's just staying in the game. If you’re doing exactly what everyone else is doing, you have no competitive advantage. You’re just a commodity. Real strategy requires the courage to be different. It requires the courage to let some customers go because they don't fit your "Where to Play."

Making It Actionable

So, how do you actually apply this? It starts with a conversation. Not a spreadsheet.

Start by asking your leadership team: "What would have to be true for this idea to be a great strategy?" This is a magic question. Instead of arguing about whether an idea is "good" or "bad," you explore the conditions under which it would succeed.

  • Would customers have to value price over quality?
  • Would competitors have to stay out of a certain niche?
  • Would we need to build a new distribution channel in six months?

Once you lay out those conditions, you can go out and test them. You don't need a year of market research. You just need enough data to see if your "How to Win" hypothesis holds water.

Step-by-Step Strategy Stress Test

  1. Define Winning: What does success look like in three years? Be specific. Revenue is a result, not an aspiration.
  2. Pick Your Battles: Write down who you are not going to serve. If you can't name a customer segment you're willing to lose, your "Where to Play" is too broad.
  3. Identify Your Edge: Why will a customer pick you over the alternative? If the answer is "better service" or "higher quality," dig deeper. Everyone says that. What is the mechanical reason you can provide that?
  4. Audit Your Assets: Do you actually have the skills to pull this off? If not, how much will it cost to build them?
  5. Check Your Incentives: Look at your payroll. Look at your meeting agendas. Do they actually support the strategy, or are they leftovers from the way you used to do things?

Strategy is simple, but it’s definitely not easy. It’s hard because it requires making choices that have consequences. It’s hard because it requires saying no to people. But in a world where everyone is trying to be everything, the person who decides to be one thing—and does it better than anyone else—is the one who wins.

The most successful companies aren't the ones with the smartest people or the most money. They’re the ones with the clearest sense of what they are and, more importantly, what they are not. Stop trying to optimize a broken logic. Start making choices. That’s the only way to actually play to win.