How to Become a More Strategic Thinker

by | Growth Strategy

Become a more strategic thinker

Immersing yourself in business books will never make you a strategic thinker. Not in a million years.

Clients and friends often ask me how I developed my “strategic thinking ability”—what they sometimes describe as my way of connecting seemingly disconnected things into a cohesive whole or direction. It’s a flattering question. While God blessed me with few gifts to accompany my many shortcomings, I don’t believe that strategic thinking is one of them. Like leaders, strategic thinkers are not born; they are made. If you’re interested in becoming a more strategic thinker, this post shares what I think were the two most important dimensions for me and resources to get you started.

First, let’s dispel the nature versus nurture argument, so those who think they don’t have this “gift” can work past their confidence issues. Yes, you need some basic skills—curiosity, problem-solving, baseline intelligence, grit, and desire. If you are reading a Jeff McKay blog, I am pretty confident that you have all those skills. Otherwise, you’d be watching the Kardashians. So, let’s just keep moving.

Strategy is nothing more than pattern recognition.

2 Marketing Schools of Thought in Professional ServicesYou look at data related to a problem and try to recognize how data points fit together. Which data points form a pattern? Which data supports a given pattern? Which data does not fit? Effective pattern recognition requires two simple things: 1. a basic framework or lens that helps you see a pattern; 2. a robust external context against which you juxtapose and test your patterns.

Number one is easy. Strategy books are a dime a dozen and the concepts are often so straight-forward and similar that you can get what you need from a Harvard Business Review article or two. Pick your favorite one, two, or three. Combine the concepts if you like, but establish some basic way of looking at a decision.

The second is a robust external context. This item is mandatory and separates great strategists from everyday thinkers. The context comes from one place and one place only—reading. Yes, reading. That means a lot of sources, a lot of subjects, and a lot of points of view—not just points of view that align with yours.

  • Warren Buffet spends 80% of his day reading.
  • Peter Drucker chose one subject every three years and read essentially every book in the bibliography of each!
  • Bill Gates reads about 50 books per year.
  • Mark Cuban reads more than three hours every day.
  • Elon Musk is an avid reader. When asked how he learned to build rockets, he said, “I read books.”

Now think about this:

  • 42% of U.S. college students will never read another book after they graduate. Source:
  • 80% of U.S. families did not buy a book this year.
  • 70% of adults have not been in a bookstore in the past 5 years.


There is no shortcut. You have to do the work.

Reading offers numerous benefits, but I like it because it forces me to do several things. One, it exposes me to others’ points of view, which makes me uncomfortable and attacks my biases. Two, it builds interconnections between seemingly unrelated subjects (religion & marketing messaging or teenage brains & management) that I might not have seen otherwise—it compounds like interest. Three, it humbles me by reminding me how little I really know, which motivates me to read even more.

When I look at the sources that have shaped my thinking, they fall into these categories (likely in this priority):

  1. Knowing how the world works,
  2. Knowing how to think,
  3. Knowing myself,
  4. Knowing business,
  5. Knowing my core discipline.

These are not mutually exclusive categories. Like I said, knowledge interconnects and compounds. If you are not sure where to start reading to become a more strategic thinker, might I suggest a good book or two—or 50?


Historian Barbara Tuchman on the power of books:

“Books are the carriers of civilization. Without books, history is silent, literature dumb, science crippled, thought and speculation at a standstill. Without books, the development of civilization would have been impossible. They are engines of change (as the poet said), windows on the world and lighthouses erected in the sea of time. They are companions, teachers, magicians, bankers of the treasures of the mind. Books are humanity in print.

Source: The Book, Bulletin of the American Academy of Arts and Sciences, Vol. 34, No. 2 (Nov. 1980)




Knowing How the World Works

When asked how he learned to build rockets, Elon Musk said, “I read books.”

Any title by David McCullough

John Adams and The Wright Brothers are a couple of my favorites. See how average people become legends and change the world. McCollough is informative, insightful and inspiring.

Bobos in Paradise by David Brooks

Brooks is an incredible social commentator. “Bobos” highlights how baby boomer executives often live, think, and buy.

Any title by Michael Lewis

I don’t know how he does it, but Lewis cracks open the best-kept secrets of life and business. Moneyball is a favorite but pick anyone.

Any title by Malcolm Gladwell

The Mystery of Capital: Why Capitalism Triumphs in the West and Fails Everywhere Else by Hernando de Soto

This book expanded my view and understanding of systems, particularly in the worlds of finance, politics, geography, poverty, and human potential.

Almost any biography

Reading how successful people struggled and worked to reach success despite overwhelming odds or personal demons is, not only encouraging, but the best way to understand how the world works.

Knowing How to Think

Any title by Peter Drucker

Drucker is the grandfather of management consulting. He squeezed more knowledge into a single page than all of the writers on my list.

The Wall Street Journal

Do I really need to list this? Get a subscription AND then read it!

Freakonomics by Steven Leavitt & Stephen Dubner

No book series has done more to break, rebuild, and expand my business thinking than this book. The data never lies. If Spock were real, he would be hanging out with Leavitt.

Freakonomics Radio

These podcasts offer all of the great thinking of the books, played out across myriad subject areas in audio. Stephen Dubner is an incredible interviewer and stand-in for us non-economists

Thinking Fast and Slow by Daniel Kahneman

The grandfather of behavioral economics and Nobel Prize winner changed how I think by teaching me about human decision making and our bias. This was humbling.

Fresh Air

In this 30-minute podcast, you are exposed to history, books, programming, politics, and social commentary. If you lean right, Fresh Air will help you understand the left. If you lean left, it will satisfy your confirmation bias (see Thinking Fast and Slow).

The Art of Possibility by Rosamund Zander and Benjamin Zander

The title says it all. Don’t limit yourself; the Zanders will open your world up to new possibilities.

The Virtue of Selfishness by Ayn Rand

42% of U.S. college students will never read another book after they graduate. 


Most people know Rand’s fictional account, Atlas Shrugged (a worthy read), but many are not familiar with her non-fiction. This book, whether you love Rand or hate her, will open up your mind to how business and societies work—and fail to work. If you cringed at Rand’s name, make sure you read it. If you smiled, listen to Fresh Air and read Kahneman.

Man’s Search for Meaning by Viktor Frankl

Frankl shares his experience inside a WWII concentration camp. You cannot read this book and not be moved by man’s inhumanity to man. More importantly, you will see how man can transcend suffering and hardship in order to thrive, even in the worst circumstances.

Knowing Myself

Learned Helplessness: A Theory for the Age of Personal Control by Christopher Peterson, Steven F. Maier, and Martin Seligman

This book changed my paradigm on human nature, including how I talked to myself and why others are unable to get out of their own ways.

The Wisdom of the Enneagram: The Complete Guide to Psychological and Spiritual Growth for the Nine Personality Types by Don Richard Riso and Russ Hudson

Forget DiSC, Myers-Briggs, and other “personality” tests. If you want to know yourself and why you behave the way you do, this is the only test. If you aren’t serious about personal growth, don’t start down this path.

The Way to Love by Anthony de Mello

This book transformed my life at a critical time. De Mello will hit you lovingly upside the head and wake you up to self-awareness. You cannot love, see the world accurately, or fully live without it.

No Man is an Island by Thomas Merton

Read this after The Way to Love. Merton is the 20th century Thomas Aquinas. His perspectives on faith, humanity, and world systems will change your view of humanity and religion.

Now Discover Your Strengths by Marcus Buckingham and Donald O. Clifton

If you want to be happy at work and build strategic powerful teams, you need to read this book. The authors will help you uncover your strengths, point the way to use them and help others do the same.

Feel the Fear…And Do It Anyway by Susan Jeffers

We all experience fear (see The Wisdom of the Enneagram). This book helped me overcome mine and unleashed a new way of seeing people and understanding their self-defeating and irrational behaviors.

Change Your Questions, Change Your Life: 12 Powerful Tools for Leadership, Coaching, and Life by Marilee G. Adams and Marshall Goldsmith

Adams shows us that we have to unlearn as much as we have to learn. I have found “unlearning” is one of the essential strengths of a strategic thinker.

The 5 Love Languages: The Secrets to Love that Lasts by Gary Chapman

This book changed my marriage and my styles of parenting and managing. Chapman offers light, but powerful thinking that improves any relationship immediately. I give this as a gift to all my prospects.

What Should I Do With My Life? The True Story of People Who Answered the Ultimate Question by Po Bronson

Like Lewis and Gladwell, author Po Bronson is a great storyteller. Strategy is about casting a vision. Bronson shares a litany of individual visions and successes that will hit you personally and professionally.

Knowing Business

Managing the Professional Services Firm by David H. Maister

This is the bible of professional services. If you are in pro services and read only one book, this is it.

The Trusted Advisor by David H. Maister, Charles H. Green, Robert M. Galford

If you are in pro services and read only two books, then this is your second book. It is the lingua franca of the industry.

The Ultimate Question: Drive Good Profits and True Growth by Fred Reichheld

This is the only book you need on customer satisfaction. Don’t read a summary of it. Read the entire book and, like the Enneagram, don’t use it unless you mean it.

The Firm: McKinsey by Duff McDonaldThe Firm: The Story of McKinsey and Its Secret Influence on American Business by Duff McDonald

Outside of working at the top of a leading consulting firm, you’d be hard-pressed to find another way of experiencing the culture, the hidden insecurities, and the use of power in the Fortune 500™ than you do in this book.

Five Dysfunctions of a Team: A Leadership Fable by Patrick Lencioni

I have never read or heard anyone sum up the dynamics of teamwork and offer a better approach to building healthy, high-performing teams than Lencioni does in this book.

Execution: The Discipline of Getting Things Done by Larry Bossidy and Ram Charan

The inability to execute is the Peter Principle in action. You have to get shit done. This book explains how business WORKS.

The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter by Michael Watkins

Nothing equips you to jumpstart strategic thinking than starting a new job at a new organization. This book is the best at showing you how to do it.

What They Don’t Teach You at Harvard Business School: Notes from a Street-Smart Executive by Mark McCormack

I read this book 25 years ago and still use the concepts I learned from the world’s greatest talent manager about how to read and work with people.

Never Eat Alone: And Other Secrets to Success, One Relationship at a Time by Keith Ferrazzi

While Ferrazzi seems about as arrogant as they come–I really had to power through the naming-dropping and self-aggrandizement to finish this book–I now know how to network. This book is worth the read.

Intellectual Capital: The New Wealth of Organization by Thomas Stewart

While this book is a little dated, it lays out a vision for the future of knowledge workers that is still relevant to business.

Competitive Strategy: Techniques for Analyzing Industries and Competitors by Michael E. Porter

The bible of strategy, if you read only one strategy book, this is the one.

The Innovator’s Dilemma: When New Technologies Cause Great Innovators to Fail by Clayton Christiansen

Learn how the most talented and educated business minds get strategically flanked because of their focus and past success. Read this after Porter.

Cracking the Value Code: How Successful Businesses Are Creating Wealth in the New Economy by Richard Boulton, Barry Libert, and Steve Samek

I thought this would be a book written so a consultant could add “author” to his CV. Instead, the conceptual model from the authors about how firms create value has shaped my thinking for more than a decade. I have yet to find better thinking on value creations and risk management to replace it.

Pick one of the following:  Marketbusters, Discovery-driven Growth, or Blue Ocean Strategy.

I add these popular titles because reading them will give you the nomenclature to join more strategic conversations. For example, when someone drops the silly term “red ocean” in a conversation you will know what he means.

Harvard Business Review

A lot of exceptional thinking is packed into this journal. If you aren’t reading HBR, you will be left behind.

HBR IdeaCast

If you can’t read or won’t read, this is your strategic learning choice. Podcasts are hosted by the talented Sarah Green Carmichael and last roughly 15 minutes, but they pack a lot of great Harvard Business smarts into a tiny window. Tune in.

Anything by Jim Collins

Collins is a delightful next-generation Drucker. He substantiates his perspective with empirical research and delivers his ideas with powerful, meaningful, memorable language. Need I say more?

The Art of War by Sun Tzu

This book had a renaissance in the ’80s. It is required reading for the best military strategist. While I hate the “business is war” metaphor, this book is a timeless gem.

Allocating Marketing Investments

Knowing My Core Discipline (Sales & Marketing)

Marketing Imagination by Theodore Leavitt

This is an anthology of Leavitt’s best HBR articles. I think it is the bible of strategic marketing and was mandatory reading for all of the marketing teams I have ever led.

The Cultural Code: An Ingenious Way to Understand Why People Around the World Live and Buy as They Do by Clotaire Rapaille

I love this book. It brings together some of my favorite subject areas: religion, sociology, marketing, and human nature. Rapaille offers powerful, real insights into how humans around the globe view core “product” categories: food, sex, transportation, money, etc. It caused a radical shift in how I see marketing.

Positioning: The Battle for Your Mind by Al Ries and Jack Trout

Most branding ideas you read today originated in this seminal book.

Trading Up: Why Consumers Want New Luxury Goods–and How Companies Create Them By Michael J. Silverstein and Neil Fiske

This title offers powerful insight into why buyers are willing to spend outside of their income level demographics and how you ignore psychographics at your firm’s peril.

Permission Marketing by Seth Godin

Read any Godin book and you will be a better strategist. This one sets up modern marketing better than anything else you will read.

The Challenger Sales by Matthew Dixon and Brent Adamson

There are three sales books on my list. I wish I had written this one because I love the philosophy, the research-backed support, and it demonstrates the power of sales and marketing integration.

Spin Selling by Neil Rackman

Often described as the definitive sales book, the title is built on solid research and offers applicable techniques. Rackman wrote the introduction for The Challenger Sale.

The New Strategic Selling by Robert Miller and Stephen Heiman

If you are in B2B, this is THE book on “complex” selling. Nothing happens in business until something is sold. This book explains how selling works.

What do you suggest?

Be prudent.

About the Author

Jeff McKay
Founder & CEO
Prudent Pedal

As a strategist and fractional CMO, Jeff helps firms set smart growth strategies in motion. He was the SVP of Marketing at Genworth Financial, the Global Marketing Leader at Hewitt Associates, and held senior roles at Towers Perrin and Andersen. Learn more.

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