13 min read

You Think You Have a Strategy. You Don't. And It's Going to Cost You.

You Think You Have a Strategy. You Don't. And It's Going to Cost You.
Photo by Matthew Stephenson / Unsplash

Ambitious visions usually go nowhere. Understanding what a strategy actually is can multiply what your organization is capable of achieving.

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S3T PodCast You think you have a strategy
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There is a surprisingly widespread misunderstanding of the word strategy.

You'll hear it in corporate boardrooms, startups, engineering organizations, technology transformation programs, and even among experienced executives. People speak confidently about having strategies. They publish strategy documents, organize strategy workshops, and present strategic roadmaps.

But ask them to explain precisely how their strategy will overcome the obstacles standing between them and their desired outcome, and the conversation gets surprisingly vague. This matters more than most leaders realize.

The Hikers had everything except...

Imagine a group of hikers excited about climbing a mountain. They're wearing matching T-shirts with the name of the mountain on them. One of them made a AI poster with a fake picture of them on top of the mountain they hope to climb. They are so stoked.

One problem: They haven't calculated how far they'll need to travel, how much elevation they'll gain, or how long the journey will take. They haven't determined how much food and water they'll need to carry or where they can replenish their supplies. They have no trail map. Nobody has assessed the weather, identified dangerous sections of the route, or determined whether everyone in the group is physically prepared for the climb. They haven't agreed on who will navigate, who will carry essential equipment, or how to handle contingencies - if someone becomes injured or if the group encounters an avalanche that requires changing course.

They have a destination, enthusiasm, and a compelling vision of success. They also have matching T-shirts, which will look fantastic in the photographs. What they don't have: a credible basis for believing they'll reach the summit safely.

This is how many organizations approach strategy.

Executives gather to discuss an ambitious future. Sticky notes and whiteboards get filled with words and shapes and arrows. Hours & days of word-smithing. A management consulting company congeals it all into a beautiful presentation, anchored on an inspiring slogan, maybe even a logo. Definitely a color scheme.

A org psych specialist or two adds another layer: “corporate culture” (a.k.a how to virtual signal going forward). The communications team creates web pages, buys branded t-shirts, stickers and stress balls. Employees attend kickoff meetings where leaders announce a bold new direction, hands out swag and tell everyone to embrace the cause.

But somewhere between defining the destination and launching the expedition, we skipped some crucial questions:

  • What are the formidable barriers that will prevent us from reaching our goal? How will we overcome them?
  • What resources, capabilities, and expertise will be required - that we don't have right now?
  • Where will the organization need to make trade-offs...and sacrifices?
  • Who is responsible for tackling each critical barrier,
  • In what sequence must things happen? What assumptions need to be tested before committing substantial resources? How will the organization know whether it's making meaningful progress or simply exhausting its people and resources along the way?

This is the non-exciting and messy work of figuring out how to actually get there.

These questions frequently receive far less attention than the PowerPoint slides and slogans. In fact these questions - valuable as they are - will be unwelcome: they‘ll be seen as negativity.

And this is where organizations make an extraordinarily costly mistake: they confuse having an exciting destination with having a strategy capable of getting them there.

Literally the difference between a poster of Mount Everest vs a climb plan for getting to the top of that mountain.

Why its so important to get 100% clear on what looks like a strategy but actually isn’t

Sometimes the supposed strategy is a vision statement. Sometimes it's a list of goals, a technology investment plan, or a collection of projects. Sometimes it's simply an aspiration to imitate a successful company or entrepreneur, without carefully examining whether the conditions that enabled that success exist in the organization's own environment.

Don’t get me wrong - All of these things can have value. But they are not a replacement for a strategy. Problems emerge when leaders assume that having these ingredients automatically produces a strategy. These things won’t get you to where you want to go. There’s something else.

And when we don’t have that “something else” the consequences extend well beyond wasted investment or disappointing execution. When we don't understand what a strategy actually is, we underestimate what a good strategy can help us accomplish. We underestimate ourselves.

We launch ambitious initiatives without establishing a credible means of overcoming the constraints that make success difficult. When results fall short, we interpret those failures as evidence that the original ambition was unrealistic, rather than examining whether we ever developed an adequate strategy in the first place.

Over time, this creates a subtle but serious leadership problem. Organizations become increasingly cautious about setting ambitious destinations. Leaders lower expectations, shorten their planning horizons, and prefer incremental improvements because previous transformation efforts have produced so little. A quiet sense of hopelessness begins to take hold, often disguised as pragmatism or being realistic.

This is an especially unfortunate outcome because ambitious achievements are genuinely possible. They require leaders who understand how to diagnose difficult problems, identify sources of leverage, understand where really difficult decisions will be necessary. They’ll need a plan that preserves scarce resources like attention, qualified talent, time and money. They’ll need to know the terrain they're about to hike into, and have the necessary preparations, provisions and conditioning to get to their destination. In other words, they'll need an actionable strategy.

This is the power of a real strategy. It gives people a disciplined way to transform improbable outcomes into outcomes they have a credible chance of achieving. Its something you can actually use to increase your success.

grayscale photo of two people walking on mountain valley
Photo by Jonathan Bell / Unsplash

What Makes a Strategy useful?

One of the clearest explanations comes from Richard Rumelt, author of Good Strategy/Bad Strategy. Rumelt identifies three essential components of a good strategy:

  • an accurate diagnosis of the challenge,
  • a guiding policy for addressing that challenge, and
  • a coherent set of actions that puts the policy into practice.

These three elements can help you distinguish genuine strategic thinking from the many things that are routinely mistaken for it.

Returning to our hikers, a diagnosis would reveal that the journey involves difficult terrain, substantial elevation gain, uncertain weather, limited access to water, and varying levels of physical fitness among the participants. The guiding policy might be to select a manageable route and season, prepare the group through progressive training, and organize the expedition around reliable resupply points and clearly defined safety margins. Coherent actions would include obtaining accurate maps, verifying trail conditions, calculating supplies, assigning responsibilities, securing permits where necessary, and establishing contingency plans.

The hikers would still face uncertainty. Weather could change, conditions could deteriorate, and unexpected setbacks might require them to turn around. But they would have significantly improved their chances of achieving their objective by understanding the challenge and preparing a coordinated response to it.

A useful working definition is this: A strategy identifies 3 things in actionable detail:

  • An outcome that is necessary but difficult to the point of being unlikely,
  • The obstacles and challenges that make that outcome unlikely, and
  • The path for overcoming those obstacles and challenges and making that necessary outcome happen anyway.

This definition is particularly valuable for business and technology leaders because it gives them a practical way to evaluate strategic proposals. When someone announces a strategy, we should be able to identify the desired outcome, understand why achieving it is difficult, and see how the chosen approach creates leverage against the obstacles.

We should also be able to explain why the organization believes its approach will work under the particular circumstances it faces.

A strategy earns credibility through the quality of that reasoning, not through the confidence with which it is presented.

How to Construct a Useful Strategy

Here is a practical approach leaders can use to move from aspiration to strategy.

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Free Readers: Sign up for S3T full access to keep reading. You'll learn step by step how to construct a strategy that changes your probability of success and communicate it effectively to your teams. You'll also get a list of recommended reads to strengthen your grip on effective strategy and execution.

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