The best business books aren’t in the management section.
…Read books about specific businesses or industries that you already know a lot about. That way, you will have enough contextual knowledge for the book to be meaningful. Of course many people don’t work at a company or industry big or famous enough that there are books about it, so I have a corollary proposition: You will learn the most about management by reading books about sports and musical groups.
And this observation is spot on:
Traditional business books, in contrast, are frequently written to get consulting work or on to the speaker’s circuit.
I would say that reading books about sports and musical groups works for Tyler probably better than it would work for most people. I myself benefited a lot from watching and re-watching a video called The Compleat Beatles, because it points out how well they were served by making connections, with Alan Williams, Brian Epstein, and George Martin. I really needed that lesson, and I took it to heart when I started my business.
Some business books have mass appeal. Like Tyler, I suspect that is because they are very upbeat and non-threatening, without being particularly insightful.
But I lean into my own idiosyncratic tastes when it comes to business books. So what I will give you below is not a list of “best” books by any objective criteria. I will instead just say why they appealed to me. And they are mostly more than two decades old. You can attribute that to a decline of quality of books or, more likely, to a decline of my patience and motivation to read.
Personality psychology
You are welcome to question the scientific underpinnings of personality psychology, but you should study it, regardless. Go back and read some of Rob Henderson’s posts on it.
If you get into a personality conflict at work, the worst thing to do is to get swept up in it. By stepping aside and seeing it as two people with different personalities, you can be more detached and serene.
If it’s detachment and serenity that you’re after, you can read something like Grist for the Mill or The Courage to be Disliked. But if you can’t stand what we used to call New Age stuff, stay away from those.
Now on to some books that employ theories of personality. Keep in mind that personality characteristics can change. You can act one way with familiar co-workers and differently at a party where you meet strangers. And you can evolve over time.
Not about business, but I got something out of reading one of Helen Fisher’s books, probably Why Him? Why Her?.
Academic psychologists scorn Myers-Briggs, but in business it is useful for seeing the positive side of every temperament. I learned it from Kiersey and Bates, Please Understand Me, which compresses down to four temperaments. You need big-picture people (N) and you need detail-oriented people (S), even though each will regard the other as stupid. You need decisive people (J) and you need people who prefer to keep options open (P), even though they will drive each other crazy. The P type will be in pain as the J’s rattle off a series of decisions during a meeting. The J type will be in pain when you’re getting to wrap things up and the P types force you to revisit something you thought got settled in the first 15 minutes.
Put various personalities together in a large organization, and you get what I call corporate soap opera, meaning the inability of people to get along and work together. A book that speaks to that is The Best and the Brightest, David Halberstam’s description of the bureaucracy that oversaw the Vietnam War.
On the obscure side, there is Intrapreneuring, by Gifford Pinchot III. For me, with my temperament, this is the most inspiring business book ever. But I would say that he is much too positive about the life of a corporate intrapreneur. It is a very frustrating role.
Because I find corporate innovation an interesting topic, I liked The Idea Factory, by Jon Gertner. I might like Fumbling the Future, about Xerox PARC, but I don’t think I ever read it. I read a long article many years ago that covered the topic.
Books where I had a distant personal connection
I think these are great books, but keep in mind that I either knew the author or some of the people profiled.
Information Rules, by Hal Varian and Carl Shapiro. Hal Varian has always been very nice to me, going back to when he gave a simple final exam for his very difficult course when I was in grad school at MIT. This is a classic book on the strategy for content businesses in the digital world.
Barbarians at the Gate, by Bryan Burrough and John Helyar. My wife is a cousin of the Wassersteins. I never met Bruce, who is a character who appears in this book, which is about an epic corporate takeover battle. His presence is a special hook for me, but I think anyone would enjoy this entertaining read.
Liar’s Poker, Michael Lewis’ first book, is also very entertaining. But I also met a few of the Wall Street traders he mentions, because they were dealers of mortgage securities back when I was with Freddie Mac around 1990.
When Genius Failed, by Roger Lowenstein, chronicles the rise and fall of a high-powered hedge fund. Fed Chairman Alan Greenspan felt it necessary to get involved in resolving its failure, and his ability to contain the damage may have fostered complacency that ended with the crisis of 2008. Some of the junior employees of the fund were in my cohort when I was in grad school at MIT.
Other
Speaking of Greenspan, Sebastian Mallaby’s The Man Who Knew is a terrific biography. I reviewed it here.
If you’re willing to back even farther, to the 1960s and early 1970s, then I strongly recommend two best-sellers by ‘Adam Smith’ (George Goodman): The Money Game, and Supermoney. Especially if you share my interest in personality psychology.
On personality psychology. My understanding of Meyers-Briggs used to be similar to Dr Kling's, and I read the 300-page manual years ago, but I have learned recently that Jung was much richer and clearer on this topic (the YouTube videos by Alexis Kingsley are a friendly introduction). The main problem is 16 types is unwieldy.
I have seen the wieldy DiSC (developed by William Marston, Harvard PhD, polymath inventor, and creator of Wonder Woman) used by multiple large organizations, and found it to be a good input for hiring decisions, ice-breaking, team-building, and development conversations. It is related to "interaction styles" and I have seen a mapping to Meyers-Briggs (on a CS Joseph YouTube video -- his early ones are good, before "fame" and divorce hit him). The Personality Indicator and Enneagrams seem to be variants, but I have little experience with them.
The Big Five is the state of the art for the academically minded. It is good, simple, and evidence-based via lexical-statistical analysis rather than theory.
I believe all of these measures add value if used prudently. For example, I would read a candidate's DiSC after I interviewed them, to avoid confirmation bias. Jung, who aimed to reconcile science and religion, will really help you understand your blind spots. Go NTs! :o)
The idea that most business books are junk strikes me as more or less correct. I've been asked to read a couple in my day as part of various managerial training programs and both were a complete waste of time. However, I'm skeptical about the value of substituting books about supremely talented athletes and musicians. I'm not sure what the business world equivalent of having a 40" vertical leap or being able to write and play a tune as catchy as "Hey Jude" might be, but any strategy that starts with that as a given probably isn't likely to work for us mere mortals.