Defining Strategic Thinking

By Diana Montalion

in Thinking | December 11, 2018

Strategic thinking is the alpha topic because crafting context gives meaning and value to everything we do.

The value of every decision we make depends on the context in which we make it. In The Lord of the Rings, Frodo’s journey to destroy the ring is meaningful inside the context of Middle Earth. Otherwise, he’s a short, hairy guy with apocalyptic hallucinations. Tolkien didn’t simply describe a journey, he crafted a framework in which the journey, and Frodo’s choices, have value. 

In the real world, crafting a framework is also the vocation of strategic thinkers. “Crafting” is an apt descriptor. Many types of thinking — creative, analytical, critical, divergent, convergent, concrete and abstract —  are central to strategic work. Alone, they are scraps of metal. Conveying ideas through writing, editing, whiteboarding, storytelling, researching, modeling, structuring, discussing, debating and re-modeling forges them into something transformative. Tolkien enabled us to see what he saw.

The ephemeral materials that give a framework structure are contextconcept and integrity. Context is an understanding of the circumstances. Concept is the abstract idea, analogy or mental image that encompasses “the circumstances.” When a framework hangs together well, clearly conveying elegant simplicity, we say the structure has integrity. Integrity is the glue that holds context together as concept evolves into reality. Middle Earth has integrity.

Contrary to popular mythos, strategic thinkers are not commanders, they are integrative and influential leaders. Daily life is 10% “I have a vision!” and 90% “We sail together towards that vision through a stormy sea.” Strategic thinkers are conceivers and midwives. Despite reliance on the mind, they embody conceptual integrity. As things change, they adapt the journey, the ships and/or the world in which they sail.

The machine you drive to the grocery store is, conceptually, a car. Imagine the millions of factors that make a car fit for its purpose, like wind resistance, reliance on gas stations, manufacturing materials, safety statistics, delivery methods and user comfort. Cars represent both profit value and real cost (to the environment, for example). Strategic thinkers design a single machine (a car) within the wider context of “car” while anticipating changes inside and around that context.

Strategic thinking is difficult to define because words fail when describing how logic is fed by the river of intuitive knowing. Strategic thinkers often borrow tools from different toolboxes, which leads to a mashup skill set rather than a single path to certification. Their deliverables are difficult to qualify or quantify because the same framework does not suit every situation. Strategic thinkers travel back and forth between complexity and simplicity like a loom, connecting with people where they are — inside their unique circumstances. They are leaders and followers, simultaneously.

If you google “strategic thinking” for a definition, you’ll see many results that instead define strategic planning. A strategic plan is a linear model developed from a situational point of view. Planning can be done by strategic thinkers (or not) but the activities are disparate. When designing a car, planning is “the cupholder conversation”. Identifying the value, to the user and the business, of cupholders, for example. Defining feature requirements like location and circumference. Setting expectations based on manufacturing-time estimations. Cupholders are important — planning is essential. Problems arise when planning is misunderstood to be the framework itself or worse … strategic leadership.

A product focus that “delivers value” to the customers exclusively without regard for the value of the technology system that generates that value is unbelievably stupidly and ridiculously expensive long term.

Like buying every foundational business tool using a credit card and making minimal monthly payments.

Worse, every product person has a credit card.”

Fred Brooks // American Computer Architect & Author, The Mythical Man-Month

Definitions that seek outcomes like “innovation” or “competitive advantage” also miss the mark. Strategic thinking more often reveals what not to do and when not to act. In the chaotic sea of stormy change, strategic integrity is a steadying hand on the rudder. Frodo does not wander off to visit Disney World on his way to Mordor because users want more Mickey; the value of his mission is clear and present. “Everybody, all together, from the beginning” is the outcome of strategic work and that is what drives innovation. Alignment. Without alignment, there is rarely conceptual integrity.

The ultimate goal of strategic thinking is wisdom. Wisdom will stand the test of time. Most initiatives will fail to achieve that goal. Regardless, aspiring to it always increases the chance of meaningful success.

Strategic thinking may be difficult to define but you know when it’s missing. Like oxygen, its absence is felt more than its presence is seen. Below is a list symptoms that indicate the level of conceptual integrity in an initiative:

High Levels

Low Levels


Siloed and hierarchical

Strong rhythm

Chaotic, interrupted rhythm



Respectful argumentation

Bullying (subtle or overt)

Trust building is evident

Lack of trust is evident

“Best possible solution under the circumstances”

“Meets requirements (or not)”

Dedicated to meaningful work

Dedicated to managing work


Information is a power currency

Better-than-expected solutions are normal

Blame is normal

Strong alignment on “best practices”

Constant in-fighting

Pattern aware

Pattern repetitive



Lead by influence and integration, present and engaged

Lead by command and control, absent yet maintains authority

Truth and insight seeking

Constantly shifting definition of “value”

Self awareness, emotional intelligence




Ask, in front of the team

Tell, in an email or private channel

Well-prepared for meetings, lots of whiteboarding

Most people are silent in meetings, collaborative visuals are rare

Empathy and respect




The upcoming articles in this series will describe a foundational skill set for strategic thinking. Argumentation is chief among them. Strategic thinkers are constantly improving their ability to align and arrive at the best possible solution under the circumstances. We’ll explore the value of empathy, self-awareness and being well-prepared for meetings. And we’ll outline practical methods for creating structure, sharing a few tools that can help.

Want to talk about strategic thinking?

Mentrix loves to help teams and organizations establish these patterns. 

Diana Montalion

About the author

If you’ve read The Economist, donated to Wikipedia, or contributed to The World Monuments Fund, you’ve interacted with systems that Diana helped to architect. She has 15+ years experience delivering initiatives, independently or as part of a professional services group, to clients including Stanford, The Gates Foundation and Teach For All. She is co-founder of Mentrix Group, a consultancy providing enterprise systems architecture, technology strategy, and content systems development. She also takes meeting notes with a fountain pen and is an aspiring plant chef.

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