Strategy is essential for every organization, yet actually crafting a sound strategy is extraordinarily difficult. This piece explores three core reasons why strategy is so hard — conflicting interests, fear of change, and uniformity of thought — with concrete examples for each. Understanding the nature of each obstacle is the very first step toward genuine strategic thinking.

1. Why Is Strategy Always So Hard?

Everyone agrees that strategy matters, yet actually getting it right is another story. Lawrence Friedman puts it plainly:

"There can be no doubt that strategy is clearly a good thing, but it is hard to escape the conclusion that doing it properly is really very difficult."

Strategy is the critical work of determining an organization's direction and future — yet the process of creating and executing it runs into countless obstacles at every turn. So why is strategy this hard? And why do most companies fail at it?

2. First Obstacle: Conflicting Interests (the Principal–Agent Problem)

One of the biggest obstacles in strategic planning is conflicting interests — the principal–agent problem. Human beings instinctively prioritize their own interests, and the managers and executives of any company are no different.

"The principal–agent problem arises when the interests of a company's owners (principals) and the managers (agents) who make decisions on their behalf are not aligned."

Managers want the company to succeed, but they tend to prioritize their own success even more. For example, when an underperforming business unit needs to be wound down, the company will typically hear first from the manager running that unit. That manager, seeking to protect their "territory," will argue: "This is only a temporary setback — with a bit more investment we can get back to growth." That is the principal–agent problem in textbook form.

To address this, companies often try to align managers with shareholders by giving them equity — but in mature organizations this rarely produces a meaningful change in behavior. Equity is highly motivating in startups and high-growth companies, but far less attractive inside large, established firms.

3. Second Obstacle: Fear of Change and the Status-Quo Instinct

The second factor that makes strategy so difficult is fear of change. Most managers are risk-averse. Even though managing risk is literally their job, the dominant unspoken norm in many organizations is: "never do anything out of the ordinary."

"In the modern corporation, managing risk means never doing anything out of the ordinary."

On the surface this attitude looks logical. Change brings uncertainty, and human beings instinctively fear uncertainty. So most organizations cling to what they already know. But in today's world, refusing to change is effectively a death sentence — because competitors are evolving without pause.

This fear of change produces only incremental strategy — small, cautious deviations from the existing path, with no room for genuine innovation. The organization sinks, inch by inch, into quicksand.

"Heraclitus said that the only constant in life is change — but he had never met a modern middle manager."

4. Third Obstacle: Uniformity of Thought and Lack of Diversity

The third factor that makes strategy so difficult is uniformity of thought. We like to think of ourselves as unique, but organizations are overwhelmingly made up of people with very similar backgrounds and experiences:

• Similar universities
• Similar career paths
• The same books on their shelves
• The same movies in their watch histories
• Mortgages and car loans to worry about

In this environment, ask the room how to enter a new market and you'll reliably hear: "build it ourselves, acquire, or partner." Ask for new product ideas and you'll get: "add five features the competition doesn't have yet" — and for the record, the managers at competing companies are thinking exactly the same thing.

People who do come up with genuinely distinctive ideas are frequently dismissed with lines like:

• "You just don't understand how the system works."
• "You're too young, you'll learn."
• "That's naive — way too far ahead of where we are."

And then there's benchmarking: the habit of chasing "industry standards." But matching the industry standard only ever means settling for average.

"In the end, we may try hard, but we have far more in common with each other than we think."

5. The Real Reasons Strategy Is Hard — and the First Step Toward Overcoming Them

The reasons strategy is so difficult can be distilled into three:

1. Conflicting interests: Because the goals of owners and managers inside an organization diverge, truly strategic decisions are genuinely hard to reach.
2. Fear of change: The instinct to avoid uncertainty keeps organizations anchored to cautious, incremental moves rather than bold, innovative strategy.
3. Uniformity of thought: A lack of diverse backgrounds and perspectives causes everyone to converge on the same ideas and repeat the same actions.

Overcoming these three factors — and the many others that compound them — is no easy task. But simply recognizing that these obstacles exist is itself the crucial first step: it means you're putting the very first button of strategic planning in the right hole.

"Breaking down these three barriers is not easy, but recognizing them is the first step toward understanding the true challenge of strategic planning."

Closing Thoughts

Strategy is hard not merely because the environment is complex, but because of human nature, organizational structure, and the limits of collective imagination. Recognizing these obstacles — and making even incremental efforts to overcome them — is what distinguishes a genuine strategist. Which of these resonates most in your own organization? 🤔