Strategic thinkers explore the uncomfortable unknown

Some people are comfortable with being known as smart and are uncomfortable with feeling stupid. They feel that they should know. However, this emphasis on concrete knowledge could be said to be the conventional and orthodox value.

Strategic thinkers focus more learning rather than knowing. Its fundamentals include a sensitivity to context, a willingness to tolerate the discomfort of ambiguity, and an ambition to explore the unknown.

Martin Schwartz, a scientist, reveals that, as a researcher, he has gotten used to the discomfort and unease associated with not knowing something. He actively seeks out opportunities to feel the discomfort. He notes, “We can’t be sure we’re asking the right question until we get a result from an experiment or an answer from some other valid source.”[i]

The lesson for strategic thinkers is to keep stretching, putting aside the feelings of stupidity and frustration. The fuzzy front end of strategy is a venture into the unknown. The better your questions, the more you increase your probability of learning something interesting and useful.

.…The above is an excerpt from Chapter 6 of How to Think Strategically: Sharpen Your Mind. Develop Your Competency. Contribute to Success., available at all major booksellers. The book’s big idea is that strategic thinking is an individual competency that can be recognized and developed. As individuals steadily improve their capacity to think strategically, the organization gains potential to craft strategy that is good, powerful, effective, clever, and nuanced.

“Careful in its research and organized in a logical fashion, How to Think Strategically is a deft business text. Both effective and complete, the guide is convincing, pushing its readership toward success and toward becoming a more skilled leader. It will be of significant value to senior executives and managers alike.”― Barry Silverstein, Foreword Reviews, August 2019

Might Christopher Columbus Change Today’s World If He Was Alive Today?

You can identify a strategic thinking narrative for any historical person or event and find useful lessons within that narrative. There are conventional accounts of what happened and why, but there are insights to be gathered from reexamining evidence to craft alternative narratives of cause and effect.

Let’s imagine that we could time-transport Christopher Columbus from the 15th century into the contemporary milieu with his X-factor of drive intact. Would he be successful? This conjecture might help us understand factors that are relevant to our situation. Context influences the answer. Moreover, it raises more questions: Would he have acquired a different knowledge of technologies that are cutting edge for our times (for example, advanced materials, mapping, management, navigation, and artificial intelligence)? What is the nature of his network with other innovators?

We can’t predict what would happen to Columbus in the modern day, but we can identify some forces that might shape the search for opportunity.

The blue oceans of opportunity today are not the same as in Columbus’s time. The technologies are different. But the Columbuses of today are just as curious, observant, and thoughtful.

I’ve heard people criticize Columbus for not knowing where he was going, not knowing where he was when he got there, and not knowing where he had been when he returned to Europe. From a perspective of strategy, this is unfair and ignores the role of ambiguity and emergence.

Students of strategy should recognize that an expeditionary mindset is valuable. The world is one of complex and emergent systems that seldom bend to the elitist notion of a strong-willed visionary genius. Paul Graham, a venture capitalist, writes, “Neither Bill Gates nor Mark Zuckerberg knew at first how big their companies were going to get. All they knew was that they were onto something.”[i] We don’t know when Christopher Columbus realized that he was “onto something.” Although he was probably a narcissist and possibly delusional, he learned and adapted to changing situations.

The Christopher Columbus strategic thinking narrative reinforces the importance of a sharp mind in touch with the situation. Columbus discovered an insight that any other competitor could have exploited. He persevered and maintained his focus on gaining strategic resources.

One of the most empowering aspects of competent strategic thinking is the realization that ordinary people can do great things. Your challenge is to sense the details of your situation and craft an effective response.

.…The above is an excerpt from Chapter 3 of How to Think Strategically, available at all major booksellers. The book’s big idea is that strategic thinking is an individual competency that can be recognized and developed. As individuals steadily improve their capacity to think strategically, the organization gains potential to craft strategy that is good, powerful, effective, clever, and nuanced.

“Get your hands on this book as soon as possible! It’s practical. It’s insightful. It’s accessible to all. Githens has the courage and experience dismantle strategy and challenge long-held orthodoxies.” Mazy Gillis

Note: I originally published this article on LinkedIn.

Adjectives tell you something important about strategy

I encourage you always to have an adjective to associate with the word strategy. For example, use the adjective clever to describe a configuration of ways and means of strategy (a clever strategy) that results in a relatively weak competitor gaining the advantage.

Another example is the use of the adjective good, which is explained in Richard Rumelt’s excellent book, Good Strategy, Bad Strategy: The Difference and Why it Matters.Good strategy has three distinguishing characteristics: a diagnosis of the situation, a set of essential choices (called guiding policy), and coherent action in the organization to pursue those essential choices. Good strategy is mostly the hard work of identifying and solving problems and exploiting opportunities. Rumelt explains that a bad strategy is one that’s all about desired performance outcomes. Bad strategy is “a stretch goal, a budget, or a list of things you wish would happen.”[i]

Everyone wants to have a strategy that’s clever or powerful or good or effective or brilliant or nuanced. Similarly, no one would be satisfied if their strategy was labeled stupid, weak, bad, ineffective, dull, or generic.

Adjectives also tell you something about strategic thinking, which is why I’ve chosen to associate the word competent with the individual strategic thinker. I encourage you to assess the individuals around you: Are they sharp minds in touch with the situation? Are they acting reasonably?

A competent strategic thinker is more likely to craft good strategy. An incompetent strategic thinker is more likely to craft bad strategy.

.…The above is an excerpt from Chapter 2 of How to Think Strategically, available at all major booksellers. The book’s big idea is that strategic thinking is an individual competency that can be recognized and developed. As individuals steadily improve their capacity to think strategically, the organization gains potential to craft strategy that is good, powerful, effective, clever, and nuanced.

“Without question one of the most useful books I have read — a must-read for all who wish to build their skills and expand their views beyond just creative, critical and systems thinking.” Paul O”Connor

[i] Bad strategy is: See Richard Rumelt, Good Strategy, Bad Strategy: The Difference and Why it Matters (New York: Currency, 2011), 42.

Are You Strategic?

Many people have been told in their performance reviews, “You need to be more strategic.” With a definite tone of frustration in their voices, they ask, “What do you mean be more strategic?”

The phrase be more strategic likely was not meant to invite the person to participate in developing enterprise strategy. The speaker more likely intended it as an instruction to enlarge one’s perspective to be less absorbed in their specialized daily work and to coordinate their efforts with the efforts of others, including sacrificing their personal efficiency to serve the broader interests of the organization.

In this sense, a person who is more strategic holds a more systematic view of the organization and its fit with the external environment. She has learned the structures and disciplines that characterize her organization and its context of stakeholders, suppliers, regulators, and the like. With this knowledge, she is able to more adroitly coordinate her activities with others.

As an adjective, the word strategic is often used as a decoration – for example, strategic leadership, strategic plans, strategic decisions, and strategic markets. Mostly, when people use strategic as an adjective, they are signaling their opinion of the importance of the noun being modified. Used this way, the adjective strategic is self-indulgent and many people use it to advance their personal status within the organization.

Most organizations have too many strategic things, a cacophony of goals and aspirations in competition with each other. The indiscriminate use of the adjective strategic adds to the ambiguity and doesn’t reduce it. Ideally, the adjective strategic should link to the organization’s strategy and ideally the organization’s strategy should be good and not bad.

.…The above is an excerpt from Chapter 1 of How to Think Strategically, available at all major booksellers. The book’s big idea is that strategic thinking is an individual competency that can be recognized and developed. As individuals steadily improve their capacity to think strategically, the organization gains potential to craft strategy that is good, powerful, effective, clever, and nuanced.

“Provides all the necessary tools and insight to help you become an influential strategic thinker. A great read.” Jeroen De Flander

Rhizomatic and Nomadic Learning

Two analogies for understanding the non-linear nature of strategic thinking

People often try to force strategy into linear plans, process, and artifacts because they desire concreteness and simplicity. That forcing seldom leads to good strategy.

These two analogies offer promise as ways to help you learn to be a better strategic thinker. They will help you grasp the essential complexity and ambiguity that is inherent to strategic thinking.

The Rhizome Analogy

A few summers ago I spent many hours removing pretty-leafed invasive ivy from a flowerbed. I would dig out a shovelful of earth and carefully pick out any trace of its root system, because a small segment of root would re-sprout. Botanists call this kind of root system a called rhizome. Rhizomes are characterized by root systems that explore, connect and reconnect, and establish new shoots.

The analogy of a rhizome is relevant to learning and practicing strategic thinking. The similarities include:

  • It is about making connections. With a holistic point of view, you can make the case that there is a multiplicity: everything is connected to everything. Similarly, every person is connected to every person. What would happen if we connected a group of competent strategic thinkers?
  • It is distributed. You can start your discovery anywhere. You can follow the thread, and end up knowing more. Yet, there will always be individuals who have a different and deeper knowledge, simply because they’ve spend more time on a different path.
  • A “rupture” line will emerge with a new shoot. If you make a digression or get interrupted, you will probably follow a different direction for your line of thought. Strategic thinking is inherently non-linear just like a rhizome. You can travel along a segment of a rhizome (such as reading a story) but inevitably some interesting point or curiosity or connection will take you in a different direction.

The rhizome analogy fits the non-linear nature of strategic thinking. Instead of an idealized and rational body of knowledge, it is better to see it as a subjective, growing, recursive, tangled, and sprouting structure.  The following graphic should help you visualize the strategic thinking rhizome.

rhizome strategic thinking

The Nomad Analogy

This metaphor refers to the individuals and small groups who are constantly moving.  Indeed, walk through any airport or coffee shop and you’ll see hundreds of people learning and contributing to work. Nomads are constantly alert to opportunity, improvising and adapting current resources.  The nomadic lifestyle is one of curiosity, networking, and sharing.

A nomad has a basic task of accomplishing work. They seek resources, knowledge when and where they can find it and rely on others.

Three Lessons

Here are three lessons that will help you be better at non-linear learning and contribute to your proficiency as a strategic thinker:

  • Pick and follow a thread for a while. See each little chunk of knowledge as something that connects to others. Don’t worry about complete, logical structures. Things will make sense, little by little.
  • Look for connections. Be ready to see the points of intersection, overlaps, convergences, and new sprouts of insight. Strive to incorporate abstract principles, models, and definitions with your own experience. Be alert for opportunities. Don’t worry about strategic thinking being a tangled mess.
  • Be an active learner. Take responsibility for your own learning. Ask questions. Don’t assume there is a nearby expert, nor that expert is correct.

References and Resources:

Deleuze, Gilles and Guattari, Félix. (2002). A Thousand Plateaus Capitalism and Schizophrenia. London: Continuum.

Rhizomatic and nomadic learning are relevant to building competence in strategic thinking. Do you agree?

Gregs new book available now

The Shapes of the Future

Simple phase spaceToday’s business consultants, strategic planners, trend-spotters, and management experts sell predictions. They are satisfying a market need. But it’s not likely they are enhancing anyone’s strategic thinking.

Instead of point predictions, it’s better to consider the shapes of the future. Here, we can draw some lessons from the so-called new science of complexity. First, we need to see that there are simple systems (which can be predictively modeled) and complex ones (which are not predictable). The nearby graphics illustrate the difference between simple and complex systems.

The notion of shapes-of-the-future gives our strategic thinking some space for considering alternatives and gaining a richer understanding of context. It allows for ambiguity and exploration and opening up for exploration by a sharp-minded person.

The figure at the top of this article depicts the “phase space” for a pendulum swinging back and forth. It traces out a simple and predictable linear pattern of forces (e.g. gravity, momentum, and time). As you can see, the line models the back-and-forth pendulum by cycling up and down as time progresses. It’s not too difficult to predict the shape of this simple, linear system.

Complex phase spaceThe nearby figure illustrates the phase space for a complex system. Notice that there is a circular disc on one plane and it appears that the system is mostly in that region, However, is another disc arcing upward. Is that an emerging new shape? Complexity theorists tell us that system is converge towards a particular area of phase space, called a “strange attractor.”

Further, the initial starting conditions influence the shape. A slight variation in the initial conditions might lead to no change in the final results or could produce wildly different final results.

Compare the two figures and you should see the difference between the notions of point predictions and shapes of the future.

Organizations are complex systems and furthermore, organizations interact with the also-complex external environment. Complexity theory tells us that we can’t predict a point in complex systems but can only roughly estimate it to be in some general region.


The point for strategic thinking is that we don’t waste energy focusing on events and visions, but rather emphasize understanding the context that produces the events.

This example can help you exercise the shapes-of-the-future question: What are the shapes of the future that are influenced by your children’s or grandchildren’s choice of college (or not) and vocation? Each of their choices has the potential to powerfully influence the shape of their future: their income, their status, their family size. As any parent would recognize decisions that are made today have effects that will be felt in the future.

Consider using words like triangulate, encircle, and fractals to help you imagine regions.

When you hear someone making a prediction, listen to them with skepticism if you listen to them at all. Do you agree?

Gregs new book available now

Tips for a Strategic Thinking Lab Book

Lab book 3We can take a lesson from Christopher Columbus’ practice of recording notes, observations, and ideas in a personal journal. Biographer Eugene Lyons closely studied Columbus’ journals, concluding that,

“The notes reveal his struggle to measure, comprehend, and master the secrets of the earth.”

In 2014, I started the practice a daily strategic thinking lab book (I prefer the term lab book over journal simply because I was trained in the sciences and it seems a little more evidence based). Although I have not been diligent on making daily part, it has been a great tool in my struggle to measure, comprehend, and master the secrets of strategic thinking. I make notes of observations stemming from conversations or patterns.  I include reflections on my emerging theories and frameworks. I add to it notes from research.

Here are a few of the things I’ve noted in my lab book:

  • Interesting conversations and personal anecdotes that help me recall specific strategic issues and context.
  • People that I want to contact, or stay in contact with, that will help me in my strategic thinking journey.
  • Books that I would like to read. That’s served as a good reminder when I’m in a bookstore or online.
  • I can see that I’ve been struggling a long time to characterize operational thinking, which is the opposite of strategic thinking. I can tell you that the struggle is less now than when I started.  Similarly, I can see that I’ve had an evolution of my thinking about the nature of conceptual mapping.
  • Definitions of some new words that I’ve learned. (Consilience or corruscating anyone?)
  • For me, a breakthrough idea was that strategic thinking is a “macro capability” composed of microskills.  I found my first attempt to list those microskills.
  • I have insights on strategic thinking scattered throughout, and I need to delve deeper into the significance of those insightsLab Book 2.

Overall the book reminds me of the importance of perspective as a quality of strategic thinking. Perspective is defined as personality plus point of view. Because of the lab book, I have a much better understanding of my own strategic thinking perspective.

I’m positive that the lab book will become a powerful tool for your learning journey. What additional suggestions and questions might you have?

Lab Book 1

Gregs new book available now