Books Every Leader, Entrepreneur, and Technologist Should Read

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Quora and other websites are full of lists of the best or most important business books to read. Most of these lists are full of recent books and bestsellers. We get caught up in the fads and fancies of our times, the management theory of the month.

Have you read the classics of business and management? Do you use the greatest available wisdom to help guide you, your venture, and your ambitions? Your dreams?

Yet without a foundation of deeper understanding, these books often just add to the clutter that so easily infects our words and minds. Companies, names, strategies, and tactics change, but the most important principles (and human nature) are timeless. These principles form a solid foundation for your thinking, that can resist the fashions of the day, and help enable you to see the forest despite the trees.

Reading the bestsellers without first reading the classics is akin to preaching the Gospel without ever opening a Bible.

The paragraphs below list books which may have been forgotten, especially by the younger generation. I selected them from my 57,000-book personal library. They represent the best of business knowledge and thinking over several decades. They contain ideas not easily found on the Internet, as they remain under copyright – and between covers, in print and occasionally digitally. (I suggest you read paper editions, as most of us learn and think more thoroughly and fluidly from paper and ink.)

Our desire to be “up to date” and current on the latest topics and buzzwords leads us away from older sources like these. Nevertheless, there are advantages to reading older business books.

First is that we have the benefit of hindsight. Any reading of business literature quickly proves how fast companies can change, because managements change. Strategies and tactics evolve, sometimes improving, sometimes collapsing. In these readings, you may find Sears among the most revered companies, IBM and Xerox at their peaks, and Nokia or Motorola the most exciting cell phone maker. (For more on the pitfalls of making predictions about specific companies, see: https://www.linkedin.com/pulse/built-last-beware-what-you-read-gary-hoover). 

In addition to demonstrating the fragility of the organizations we build and lead, these stories force us to ask, “Why?” They encourage us to do more research to seek the weaknesses that were not obvious when these formerly great companies were at their peak.

 Most important, reading old stories makes us consider, “How does this lesson apply today? What would that great leader do if he or she were in my shoes? How do I translate the lessons of the greats (and not-so-greats) of the past to today?” 

Whether we are studying Apple and Amazon today or Eastman Kodak and General Motors in the 1960s, we must always make translations to our own situation. While studying Amazon may seem easy and not provoke our deepest thinking, reading about the greatness of Sears does not allow us this ease. Reading these classic ideas and examples requires us to think, to exercise our brains. They need it, like any other muscle.

(If you look on Amazon for these books, note how few reviews some of them have. They’re often lost in the dust of time. Use the “Look Inside” to study the table of contents and index, to know what is covered in each book. I have included Amazon links to printed editions for your convenience, but many are also available in Kindle and other eBook formats, and sometimes from your local used or new bookstore. For those on a budget, most of these older, widely-read books are also available as clean, used copies, often for under $5.)

The Starting Point: Peter Drucker

Peter Drucker was born in Austria in 1909. He studied economics, worked in cotton trading, was a journalist and writer, earned a law degree, and worked in insurance and banking before becoming a management consultant. By 1943, he had fled war in Europe and become a naturalized American citizen. That same year, senior General Motors executives asked him to do a “social-scientific” analysis of GM, then the world’s most successful company.

Drucker became the top “business philosopher” that the world has yet known. He believed in the importance of people and invented the term “knowledge worker,” foreseeing the huge change in our occupational mix as heavy industry automated. I heard him speak almost twenty years ago, when he was in his 90s. He told us that immigration would be the most controversial topic of coming decades. The topic of immigration was far from the headlines or bestsellers at the time. Drucker could often see the future – because he deeply understood the past and present.

Throughout his writings, Drucker pointed out that the only purpose of an organization is “to create a customer,” and that the only things that really matter are innovation and marketing (defined as understanding and meeting the needs of those customers).

He spent his career as a professor and consultant, writing 39 top-selling books which have been translated into 36 languages before passing away in 2005 at the age of 95. Drucker’s talks and advice were eagerly attended by for-profit and non-profit CEOs from around the world. His books live on, at least for those with the imagination to think, “What would Peter Drucker say?”

For the last 56 years I have been studying business and economics, working on Wall Street and for big corporations, starting companies, teaching business, leading workshops, making speeches, and meeting tens of thousands of executives and entrepreneurs. Often, the most common weakness I see is a failure to holistically understand the context in which we operate.

Peter Drucker stands out in my mind because he deeply understood business, economics, government, demography, geography, history, and society at large. He integrated all these disparate parts into a holistic worldview. He thought and wrote from this broader view of the world, a bigger understanding we could all use, but too often don’t take the time to study and grasp.

The biggest challenge with Drucker is, where to start? I think his best book is:

Management: Tasks, Responsibilities, Practices (1973)

The excellent, unaltered paperback edition is hard to beat (https://amzn.to/2FSQnkd).

Take Management slowly; it is not a book to be taken lightly. Think about each idea that you read, about its implications and about how it might apply to your organization. Given that the book is over 800 pages long, it is best to focus on each of the 61 chapters gradually, over time. The chapters are digestible, averaging under 15 pages each. Think of this fat book as a Bible of sorts.

Once you have become comfortable with Drucker’s intensity of thought and style of exposition, you can learn more from his other voluminous writings. Two excellent books are:

The Essential Drucker (2001) contains 26 chapters about management and leadership from his many books, of which only 4 chapters are repetitions from Management. Thus this book is a good follow-up to Management, both reinforcing concepts and introducing new ones from his most important writings. (https://amzn.to/2G1jSiU)

Innovation and Entrepreneurship (1985) is his best look at startups and entrepreneurship. I made it required reading in all the entrepreneurship courses I taught. (https://amzn.to/2Ti4lPA)

 Once you have become a “friend” of Drucker’s, a “daily devotional” is:

The Daily Drucker: 366 Days of Insight and Motivation for Getting the Right Things Done (2004) is excellent. Each day’s entry is only one page, so it is bite-sized. (https://amzn.to/2G1qi1y)

And, if you really enjoy getting to know him, read his fascinating semi-autobiographical book, which is really about the people he met, from media visionary Marshall McLuhan to Alfred P. Sloan, who built General Motors and was arguably the greatest business manager in history:

Adventures of a Bystander(1978). (https://amzn.to/2TfNs81)

Beyond Drucker

Prioritizing the remaining books on my list is not easy. Each has something to offer.

My favorite general management book since Drucker’s passing is:

Hidden Champions of the 21st Century: The Success Strategies of Unknown World Market Leaders, by Hermann Simon (2009). While the title sounds narrow, the cases are of companies you probably have not heard of, and many of the stories are of European companies, this is an outstanding book every leader should read. German management thinker Simon is one of the few organizational observers who uses the word “will” to talk about what it takes for an organization to succeed, often beyond their greatest expectations. An awesome book! (https://amzn.to/2G7zBND)

At or near the top of any leader’s agenda is “strategy.” While our business schools nearly worship the intelligent work of Michael Porter on the subject, I think the best single, most useful book on strategy is:

Good Strategy Bad Strategy: The Difference and Why it Matters, by Richard Rumelt (2011). Rumelt uses vivid examples to illustrate his enlightened ideas about strategy. (https://amzn.to/2TmS9NH)

Along with ever-present strategy, one of the hottest topics in recent years has been innovation, especially how to make innovation happen. I have many books on the subject, but one stands head and shoulders above the rest:

The Innovator’s DNA: Mastering the Five Skills of Disruptive Innovators, by Dyer, Gregersen, and Christensen (2011). Harvard Business School’s Clayton Christensen has written a series of important books, but I found this one that he and his colleagues wrote particularly relevant. My own interests have centered around innovation in every industry and every country. There is a lot of tripe out there, and a great many decent articles which were needlessly fattened into book-length. In contrast, I think this book hits the nail precisely on the head. Based on studies of some of the greatest innovators of our era, the authors distill the diverse patterns down to a few simple principles, the most important being “combinatorial thinking.” (See https://www.linkedin.com/pulse/single-most-powerful-source-innovation-gary-hoover) This book is a real winner! (https://amzn.to/2TmS9NH)

Peter Drucker said that only innovation and marketing matter. While Drucker thought of marketing as figuring out and then responding to your customers’ needs, a narrower but also useful definition is “getting the word out” – branding, advertising, and all that. In those regards, the most important thing to understand is “positioning,” on which one book still reigns supreme:

Positioning: The Battle for Your Mind, by Al Ries and Jack Trout (1981). Get an original edition of this book, not any later revisions. While some of the stories are old, you learn a lot from them; and even more from the positioning stories that continue today, like FedEx. Every person interested in marketing should read this book before any other. This is strategy: most of the rest of marketing is tactics, the requirements of which change continually, from billboards to Facebook. Ries and Trout went on to separately write many good books, but almost all of those ideas flow from or parallel this one. (https://amzn.to/2Th2x9D

Al Ries’ book on Focus is another favorite (https://amzn.to/2G46Fpt).

The foundational books listed above will keep you busy for a while and introduce (or reinforce) critically important concepts. But they only scratch the surface of what can be learned by ambitious readers.

Seeing Things Differently

Like other fields, business philosophy and strategy are full of “common wisdom” – things that “everyone” knows or believes, that we often take for granted. In this context, it is worth reading smart writers who take a contrarian position (a tactic also used by many famous investors). Here are two that I urge everyone to read:

The Puritan Gift: Reclaiming the American Dream Amidst Global Financial Chaos, by Ken and Will Hopper (2008). This very contrarian book, written by two smart British brothers based on their lifelong study and action in business, is meant to make us rethink common wisdom. They even argue with Peter Drucker! But engaging your mind in this contest of ideas is one of the best ways to strengthen that important organ. While written in reaction to the financial crisis which took place a seemingly-long ten years ago, we can all rest assured that we have not seen the last such economic decline or crisis. (https://amzn.to/2CMFI6r)

The Management Myth: Why the Experts Keep Getting It Wrong, by Mathew Stewart (2009). This book is an entertaining and critical review of business education and consulting, bursting quite a few balloons along the way. The key here is to provoke the reader to say, “Well, what do I think? Why is this author right or wrong?” An excellent exercise for any mind! (https://amzn.to/2MANeGa)

Another smart, sometimes contrarian author on management is Henry Mintzberg; try starting with Mintzberg on Management (1989). (https://amzn.to/2MB5Wxn)

Spreading Your Wings

The United States has evolved into the largest, most successful, and most powerful business economy in the world. As a result, America has dominated business studies and thinking. Nevertheless, we lose out on much intelligence by not reading the works or “foreigners,” as indicated by Hermann Simon and the Hopper brothers listed in the preceding paragraphs. Here are two of the best and most thought-provoking books:

Six Thinking Hats, by Edward de Bono (1999). Wikipedia refers to Edward de Bono as “a Maltese physician, psychologist, philosopher, author, inventor, and consultant.” He is a very diverse and smart fellow who has written at least 50 books, of which this one is his most popular. While debates rage about the sources and methods of creativity and new ideas, every reader can glean some provocative nuggets from de Bono. ( https://amzn.to/2SdNaBe)

An excellent deep, serious look at creativity and how it works can be found in Explaining Creativity: The Science of Human Innovation, by R. Keith Sawyer (2nd edition, 2012). (https://amzn.to/2CMfIs2)

Twenty-One Ideas for Managers: Practical Wisdom for Managing Your Company and Yourself, by Charles Handy (2000). This Irishman could be called an “organizational philosopher.” This book is a great starting point before proceeding to his many other works. (https://amzn.to/2B41pis)

Knowing the Background

One of the most common gaps of understanding among business and other leaders is that they lack of a sense of history. You cannot know where you are going if you don’t know where you are coming from. Peter Drucker understood the societal context in which organizations live, but he also had a great sense of history. Even Steve Jobs said, “You can’t connect the dots looking forward; you can only connect them looking backwards.“ The fully educated leader should know where all these modern practices and ideas came from. To learn business history, I recommend two books:

The Visible Hand: The Managerial Revolution in American Business, by Alfred D. Chandler, Jr. (1977). This award-winning book by our greatest business historian and historical business analyst is the definitive history of how our big companies came to be. Those readers who enjoy American history will really love it, but every serious organizational leader should read it. (https://amzn.to/2Uid8kA)

For lighter reading, a sampling of great leaders and entrepreneurs, you cannot beat:

They Made America: From the Steam Engine to the Search Engine, by Harold Evans (2004). Evans is an outstanding writer and story-teller who became interested in business after he moved from Britain to the United States. This is a great book for readers of any age, broken into short articles about very diverse individuals and their enterprises. Make sure to get the hardcover original edition – the paperback leaves out the pictures which vividly tell much of the many stories. (https://amzn.to/2Wvfte2)

For short takes on some of the most interesting and innovative leaders in history, often unknown to most of us, see the biographical stories at https://www.archbridgeinstitute.org/american-originals/, many of which I wrote.

“Supplemental Reading”

As a lifelong lover of books – and business – I could list hundreds of books “you should read.” Above I have listed some of the ones I think most crucial to thinking about leadership. Here are quick bits on a few other books that may interest the ambitious learner, even including some recent ones!

Universal Principles of Design, Revised and Updated: 125 Ways to Enhance Usability, Influence Perception, Increase Appeal, Make Better Design Decisions, and Teach through Design, by Lidwell, Holden, and Butler (2nd edition, 2010). Do not be misled into thinking this book is just for architects and graphic and website designers. It is a goldmine for anyone who plans anything, deals with people, or who thinks! Get it! (https://amzn.to/2sNJGqO)

Data Science for Business: What You Need to Know About Data Mining and Data-Analytic Thinking, by Provost and Fawcett (2013). “Big Data” is now bigger than big, pervasive in business discussions. This excellent book opens the door of understanding to us mortals, not just highly trained scientists and analysts. Learn enough about all this stuff to intelligently discuss it, how to apply it in your world, and hopefully how to keep it moving in the right direction. (https://amzn.to/2Um0XTU)

The Sharing Economy: The End of Employment and the Rise of Crowd-Based Capitalism, by Arun Sundararajan (2016). Equally hot are discussions and books about the “network” economy. I found this one to be the best single book on the subject. (https://amzn.to/2Wn7iAr)

A related classic, must-read book, especially for those in the technology and media industries, is Information Rules: A Strategic Guide to the Network Economy, by Shapiro and Varian (1998). Shapiro and co-author Hal Varian, now chief economist at Google, saw the coming world well before most others. This book remains relevant, even in our fast-changing world. (https://amzn.to/2UgEQOw)

Turning Numbers into Knowledge: Mastering the Art of Problem-Solving, by Jonathan Koomey (3rd edition, 2017). Power up or fine tune your ability to, in fact, turn numbers into knowledge. And if you are lucky, into wisdom. (https://amzn.to/2ThrZf8)

Whether we realize or or not, we all think in models. A map is a model of a place. An organization chart is a model of an organization, as in many ways is a financial statement. Clear, logical thinking in models accelerates our understanding of the world around us. This biggest challenge is that once we find a model that we like, that we think “works,” we tend to get lazy and stop considering alternative models. That is not good! When addressing any intellectual question or business challenge, the more models we have access to, the more tools in our toolkit, the more likely we are to succeed. I therefore add one brand-new book, nearly an encyclopedia of diverse models and how to apply them: 

The Model Thinker: What You Need to Know to Make Data Work for You, by Scott Page (2018). As above, don’t let the title mislead you into thinking this book is just for scientists or “data people.” Every page will make you think about ideas, about people, and beyond. (https://amzn.to/2RV0A5W)

For a broader understanding of the present world around us and where it is headed, critical for any curious and successful leader, these are my favorites:

Enlightenment Now: The Case for Reason, Science, Humanism, and Progress, by Steven Pinker (2018). Excellent writer and psychologist Pinker takes a vast look at where the world is today, and what the trends tell us about the future. Bill Gates, a broad-minded and voracious reader, also loves this book. (https://amzn.to/2DCmWk1)

Factfulness: Ten Reasons We’re Wrong About the World – and Why Things Are Better Than You Think, by the Rosling family (2018). Hans Rosling was a great thinker and global researcher, but his son and daughter had to finish his book after he passed away. This is another book that Bill Gates has urged everyone to read. (https://amzn.to/2TjUN6E)

Those who are committed to learning will find much of value in the books listed above. But they are only an initial doorway to understanding. To understanding which goes well beyond anything the Internet has to offer, as wonderful as it is. If you would like more book ideas – 160 of them on subjects from history to geography to entrepreneurship, as well as my quick method for grasping a book, get:

The Lifetime Learner’s Guide to Reading and Learning, by Gary Hoover (2017). Available in print or Kindle versions. (https://amzn.to/2WkaM6C)

For my advice on dreaming up ideas, innovation, and starting and building companies, see:

The Art of Enterprise, by Gary Hoover (updated edition 2009). Used in graduate and undergraduate courses in entrepreneurship, it is only available in PDF form at this time. (https://garyhoover.dpdcart.com/product/136602)

If you would like book recommendations on business, economics, or almost any nonfiction subject, do not hesitate to email me at gary@hooversworld.com.  You can find my book reviews and articles at https://hooversworld.com/ and my videos about books, business, and other subjects at https://www.youtube.com/hooverbits/.

Gary Hoover  

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