Everyone Has a Strategy. Until You Ask What It Is.

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Written By Jeff Winter

Ahhh… “strategy.”

It may be one of the most frequently used words in business and one of the least consistently understood. Companies have corporate strategies, growth strategies, product strategies, marketing strategies, sales strategies, technology strategies, talent strategies, AI strategies, customer strategies, and probably strategies for determining which strategies require their own strategy. Everyone is encouraged to “think more strategically.” Leaders want more strategic conversations. Projects are described as strategic. Nearly every major decision is somehow connected to a strategic priority.

Yet when you ask people to explain what strategy actually means, the answers tend to drift all over the place. One person describes the company’s ambition. Another explains the annual operating plan. Someone discusses the budget, while someone else lists the major initiatives already underway. All of those things matter, but they are not necessarily strategy. That creates a serious problem. When an organization lacks a shared understanding of strategy, it can spend enormous amounts of time discussing it without ever making the choices required to create it.

My Path Into Strategy

Moving from sales into marketing exposed me to strategy in a much bigger way, particularly go-to-market strategy. Over time, that grew into leading strategic initiatives, developing industry strategies, and helping shape overall company business strategy. I could inherently see the value. When markets, customers, investments, and priorities became clearer, nearly everything downstream worked better.

Earning my MBA in 2023 was when the light bulb really went off. I realized strategy was a formal field with decades of research, methods, frameworks, and competing schools of thought behind it. Most recently, being part of Wharton’s Chief Strategy Officer program reinforced just how much depth exists within the discipline and how much there is still to learn. Strategy is a fascinating field, but it requires patience. It is a long-game activity with very little immediate reward, which makes it especially satisfying when I eventually see how the work changed the direction or performance of a company.

So, What Is Strategy?

The definition I keep coming back to is:

Strategy is a coherent set of choices that focuses limited resources on overcoming the most important barriers between where you are and where you want to go.

I like this definition because it is broad enough to apply across industries and functions, but specific enough to be useful. Every organization has an ambition. It also has limited money, people, time, capability, and attention. Between its current position and its ambition sits a collection of obstacles: competitors, customer behavior, internal silos, legacy systems, skill gaps, regulations, market conditions, weak capabilities, conflicting incentives, and countless other forms of resistance.

Strategy identifies which barriers matter most and concentrates the organization’s resources on breaking through them. That is where the kayak analogy comes in.

Imagine trying to move down a river toward a specific destination. The water is moving, the route is not perfectly clear, and the river is filled with rocks, currents, branches, narrow passages, and unexpected turns. You cannot remove everything standing in your way, nor can you explore every possible route before moving. You have to read the conditions, choose your path, commit your energy, and adjust as you learn. Some obstacles can be avoided. Some require a temporary detour. Others are simply part of the route and must be powered through. The important part is that each decision is connected to the destination and to an understanding of the conditions ahead.

Without strategy, everyone may still paddle extremely hard, but effort alone does not guarantee progress. Different teams can pursue different routes, solve different problems, and optimize for different outcomes while each sincerely believes it is helping the organization. Occasionally, someone may even paddle upstream with tremendous enthusiasm.

Strategy and Planning Are Different

One of the biggest sources of confusion is the tendency to treat strategy and planning as interchangeable. They are closely connected, but they serve different purposes.

Strategy defines the choices and logic that guide the organization. Planning organizes the activities required to act on those choices.

In the kayak analogy, strategy determines the destination, the general route, the obstacles that matter, and the logic behind how you intend to navigate them. The plan determines who is paddling, what equipment is needed, how responsibilities are divided, when progress will be reviewed, and when everyone is stopping for lunch. A plan can be incredibly detailed without containing much strategy.

It can include projects, milestones, owners, budgets, metrics, deadlines, and status reports. Those elements help organize work, but they do not necessarily explain why the work was selected, how the activities reinforce one another, or how the organization expects them to overcome the barriers standing in its way. This is why an organization can execute its plan successfully and still produce disappointing results. It may complete every project, hit every internal milestone, and remain no closer to establishing a meaningful advantage or reaching its broader ambition.

Excellent execution of weak choices is still weak strategy. It is simply more organized. A good strategy also remains useful when the plan encounters reality, which it always does. Competitors react. Customers change their behavior. Technology advances. Regulations shift. Budgets move. An unexpected rock appears exactly where the carefully prepared route said it would not. The plan must change, but the strategic logic can continue guiding decisions. A plan tells people what they are expected to do. A strategy helps them decide what to do when the plan no longer fits the situation.

The Alignment Problem

The widespread confusion around strategy is not merely semantic. It has measurable consequences. Cascade’s 2026 State of Strategy Report found that 81% of respondents said their departments pull in different directions, while only 27% said all teams understand the organization’s priorities and how they contribute to them. The report also found that 77% lack effective and consistent strategy reporting, while 74% of leaders cannot access the data they need to make strategic decisions.

That sounds less like one coordinated organization navigating a river and more like several kayaks leaving from approximately the same location while arguing about the map. The people involved may be capable, committed, and extremely busy. But hard work does not create alignment by itself. When departments interpret the direction differently, increased effort may simply allow them to separate faster.

AchieveIt’s 2025 State of Strategy Execution report found that 77% of leaders said departmental silos hinder strategy execution and innovation. That is important because silos are not only communication barriers. They can create different incentives, priorities, definitions of success, investment decisions, and interpretations of the company’s direction. There is also evidence that many strategies are simply not very strong. In 2025 McKinsey surveyed 416 senior executives in late 2024 and early 2025 and found that only 21% believed their strategies passed four or more of its Ten Tests of Strategy, a 40% decline from the comparable result roughly 15 years earlier.

The problem, then, is not that companies lack documents labeled “strategy.” Most organizations can produce those. The real question is whether those documents contain coherent choices, whether the organization understands them, and whether resources and decisions actually follow them.

Why Strategy Gets Deprioritized

Strategy is often undervalued because its contribution can be difficult to see in the short term. A company can buy a machine, launch a product, hire a team, open a facility, or implement a new system and point to something tangible. Strategy often creates value indirectly by improving the choices behind those investments. You do not usually make a strategic decision on Monday and celebrate the full result on Friday. The impact develops over time as resources shift, capabilities grow, market positions strengthen, activities begin reinforcing one another, and people make more consistent decisions. That delay makes strategy easy to deprioritize behind whatever feels urgent right now.

Unfortunately, much of the urgent activity inside companies is created by unresolved strategic questions. When priorities are unclear, teams launch overlapping initiatives. When choices remain vague, resources are spread thinly. When leaders avoid deciding what matters most, employees spend more time negotiating priorities, escalating conflicts, and coordinating work that was never aligned in the first place.

Companies will spend millions implementing technology or restructuring the organization, but may invest relatively little in determining which barriers they are actually trying to overcome. We often spend more money improving the paddles than deciding how to get through the rapids.

Strategy Is a Long Game

This is also what makes strategy so interesting to me. The work requires understanding markets, customers, competitors, capabilities, operations, investment, organizational behavior, and execution. You are looking across the entire system and trying to identify the relatively small number of choices that can create a disproportionately large effect.

There is rarely instant gratification. The impact may show up slowly through sharper priorities, stronger positioning, better investments, more focused sales activity, clearer product decisions, improved alignment, or opportunities made possible by capabilities built years earlier. Sometimes the results appear in revenue. Sometimes they appear in decisions the company stops making, work it no longer funds, or distractions it finally avoids. Often, the impact is easiest to see in hindsight. You look backward and realize that the organization now serves different markets, possesses different capabilities, makes better decisions, or occupies a much stronger position than it did several years earlier.

The kayak eventually emerges from the roughest section of the river, and the route can look obvious afterward. It rarely felt obvious while you were navigating it. That is the patience strategy demands, and it is also why I love seeing the impact.

Ahhh… strategy. Nearly everyone uses the word. Many organizations have a plan. Far fewer have made the coherent choices required to focus their resources, align their people, and break through the obstacles standing between where they are and where they want to go. Considering the amount of wasted time, effort, and investment that strong strategy can prevent, it may still be one of the highest-impact and lowest-cost investments available to a business.

References:

Jeff Winter
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