I
 recently read Brad Stone's book on Jeff Bezos and Amazon entitled The 
Everything Store. It's a good job of reporting on a topic of broad 
interest, given Amazon's unique history and powerful position. I learned
 a lot of facts about the key people, filled in some gaps in my 
understanding of the overall timeline, and heard personal impressions 
from some of the key people involved. I couldn't point to any particular
 page and say that I could have done it better.
And yet I wanted 
more. Stone does a fine job on the "what" questions, he has interviewed 
perhaps more of the principals than anyone else, and the writing is 
clear throughout. Why then does this not feel like a great business 
book? That's where my thinking turned next, and what I will discuss this
 month: after analyzing some commonalities among books that have changed
 my thinking, I divide my pantheon into two different camps then try to 
identify some common aspects of "greatness."
OK, professor 
know-it-all, what are some great business books? Let's start there, 
because the alphabetical list shows what I have found sticks with me 
over the years: hard-won narrative lessons, and deep conceptual muscle.
Peter Bernstein, Against the Gods
Frederick Brooks, The Mythical Man-month
Alfred Chandler, The Visible Hand
Yvon Chouinard, Let My People Go Surfing
Clayton Christensen, The Innovator's Dilemma
Annabelle Gawer and Michael Cusumano, Platform Leadership
Tracy Kidder, The Soul of a New Machine
Marc Levinson, The Box
Michael Lewis, Moneyball and Liar's Poker
Carlota Perez, Technological Revolutions and Financial Capital
Honorable mention (the authors probably wouldn't call these business books):
Atul Gawande, Better
Bruce Schneier, Secrets and Lies
Nassim Taleb, The Black Swan
What's
 missing here? I don't know the Drucker corpus well enough to pick a 
single volume there. I've never had much Velcro for self-help/personal 
effectiveness books, so that wipes out a lot of people's favorites, 
including Stephen Covey. I've admired Ron Chernow (Rockefeller) from a 
distance, so one day that might go on the list. Isaacson's Steve Jobs 
biography was rushed to market and thus too long. I never read Andy 
Grove's Only the Paranoid Survive in the day, but maybe it bears a 
second look.
There's another category of exclusion, the "we found
 the pattern of success" books that do no such thing. The exemplars here
 are Good to Great and In Search of Excellence, the Tom Peters/Robert 
Waterman sensation from 1985 that helped bring McKinsey to the front 
page of the business press. Taking the more recent book first, of Jim 
Collins' 11 "great" companies, only 2 (Nucor and Philip Morris) 
seriously outperformed the S&P over the following decade. Most of 
the other nine generally reverted to the mean, or in the case of 
Gillette, got bought. Most telling, just as Gary Hamel bet his 
reputation on Enron in his book Leading the Revolution, Collins got 
stuck with some outright clunkers, most notably Circuit City and Fannie 
Mae, while Pitney Bowes lost half its market cap. Did they somehow board
 the wrong people on the bus all of a sudden? I strongly doubt it. As 
for Peters and Waterman, Business Week published a cover story only TWO 
YEARS AFTER PUBLICATION showing how many of the 62 "excellent" companies
 were nothing of the sort. Retrospective pattern discovery at the 
company level, rife with cherry-picking, has yet to reliably predict 
future performance (in book form at any rate: I can't speak to what 
happens inside Berkshire Hathaway).
Ah, but what about the 
classic strategy tomes? Porter's Competitive Strategy, Hamel and 
Prahalad's Competing for the Future, and maybe Blue Ocean Strategy have 
their place, of course, but they all felt like exercises in hindsight 
bias rather than scientific discovery: the subtitle of Porter's book is,
 justifiably I think, "Techniques for Analyzing Industries and 
Competitors" and nothing to do with action. I have yet to see a 
strategic move in the real world that felt deeply linked to any of these
 efforts (that doesn't mean there are none, just that I don't see any). 
There's an old joke that sums up this orientation:
How do you spot the strategy professor at the racetrack?
He's the one who can tell you why the winning horse won.
In
 contrast, my personal list of the best business books veers away from 
such methodologies in one of two ways. First, a skilled writer, a 
self-aware founder/principal, or a combination of the two tells a story 
rich with personal experience in a highly particular situation. Second, a
 deep thinker creates a powerful conceptual apparatus that endures over 
time. (Moore's Crossing the Chasm was a near-miss here.)
Many of 
these books are striking in the modesty of their origins: Christensen 
started by knowing the disk drive industry inside and out, while Gawer 
was able to understand platforms after getting great access at Intel to 
see the company's handling of the USB standard during her Ph.D. 
research. Tracy Kidder -- one of our era's great storytellers -- 
compellingly documents the creation of a computer that never made it to 
market.
The best first-person tales were not unabated triumphs: 
Chouinard nearly lost Patagonia after some serious missteps, while Fred 
Brooks learned about software development the hard way, shipping an IBM 
operating system late. At the same time, some of the big brains 
attempted syntheses of stunning breadth: the whole idea of risk, in 
Bernstein's case, or the modern managerial organization, for Chandler. 
Both books, I suspect, were decades in the making.
On to the fundamentals: what makes a great business book? I would submit that it have some mix of four qualities:
1) Honesty
It's
 easy to paper over the messy bits; "authorized biographies" can be so 
hagiographic that all the sugarcoating makes one's teeth hurt. In 
contrast, the humility of a Fred Brooks or Yvon Chouinard is refreshing,
 frankly acknowledging the role of luck in any success that has come 
their way.
2) Human insight
Business, taken only on its 
own terms, can be pretty boring. But as part of "life's rich pageant," 
as Inspector Clouseau put it, business can become part of themes more 
enduring than inventory turns or new market entry. The best books 
connect commercial success to aspects of human drama.
3) Continued applicability
The
 retrospective nature of book publishing can be a curse, in the digital 
era particularly, but it also means that great research and storytelling
 stand up over time. A model should continue to help organize reality 
for years after publication, and the likes of Bernstein, Chandler, 
Christensen, Levinson, and Perez have earned their stature by delivering not just 
an investigation but a way of seeing the world.
4) Subtlety of insight
All
 too often, business books worship at the altar of the obvious. 
Acknowledging the facts of the situation and then deriving deeper 
principles, either by astute observation (hello Michael Lewis) or by 
rigorous scholarship, is a gift.
In the end, we find a collection
 of great business books illustrate a conundrum: just as with business 
itself, knowing the principles of business book greatness makes it no 
less unlikely that a given individual will achieve it. Luck still has 
something to do with it, and I doubt that most artists wanting to create
 a masterpiece ("the Great American Novel" for instance) actually did 
it. 
Yet for all the dashed hopes of finding a science of 
success, and for all the ego trips and bad faith, there are times when 
stories from the arena of commerce transcend the genre and deliver gifts
 of insight far more meaningful than simply how to make more money.