The titles listed below, though not required, are classics that merit a place on every aspiring leader's bookshelf:
Communication
You cannot lead if you cannot communicate. A corollary is that you should hone your communication skills for the rest of your life.
Make It Clear: Speak and Write to Persuade and Inform, Patrick Henry Winston. MIT Press, 2020. ISBN: 9780262539388.
Make It Clear is 6.803 on paper, both more and less. More on communication, less on leadership.
The Elements of Style, 4th edition, William Strunk, Jr., and E. B. White. Pearson, 1999. ISBN: 9780205309023.
Just after I distributed a draft of my first textbook, a student lobbed the dreaded question at me. “Have you read Strunk and White?” she said. I was betrayed because I had not deployed active verbs.
BUGS in Writing: A Guide to Debugging Your Prose, 2nd edition, Lyn Dupré. Addison-Wesley, 1998. ISBN: 9780201379211.
Once Strunk and White is in your blood, read Dupré. She is a developmental editor; that is, she not only performs the lesser, comma-correcting function of a copy editor, she also comments on clarity and structure. After I wrote a few books, I thought I had learned what ordinary copy editors have to teach, so I asked my publisher to find an editor who could make me cry. They found Dupré. She did.
The Visual Display of Quantitative Information, 2nd edition, Edward R. Tufte. Graphics Press, 2001. ISBN: 9780961392147.
Because we think with our eyes as well as our mouth, illustrations should properly stimulate your reader's visual problem solving apparatus. In this domain, Tufte's book reigns supreme. Look at the illustrations and discover what he has to say about them. Note, however, that you are likely to be disappointed by the writing style at the sentence and paragraph level.
Writing Models
We mimic what we read, so before you write, read something you admire.
Battle Cry of Freedom: The Civil War Era, James M. McPherson. Oxford University Press, 2003. ISBN: 9780195168952.
If I don't feel like Shakespeare, I read McPherson, who does Strunk and White great honor in the way he uses verbs. Battle Cry of Freedom is the best one-volume treatment of the American Civil War and takes you beyond high-school simplifications toward an understanding of the complex economic and political roots of a horrible war.
Molecular Biology of the Gene, James D. Watson. Pearson, 2013. ISBN: 9780321762436.
Before you write a textbook or documentation, study Watson's first edition if you can find it (the Seventh, cited above, is now available, but multiply authored, so I expect it is less well done). Do not study the biology, study the way Watson explains the biology.
How Science Works
The Trouble With Physics: The Rise of String Theory, The Fall of a Science, and What Comes Next, Lee Smolin. Mariner Books, 2007. ISBN: 9780618918683.
In the final chapters of The Trouble with Physics, Smolin explains that tenure decisions focus on maximizing the short-term reputation of the tenuring university. Accordingly, paradigm-shifting geniuses often end up as false negatives because they do not necessarily develop the expected portfolio of papers in refereed journals while they are thinking their deep thoughts. My experiences in Electrical Engineering and Computer Science run amazingly parallel.
The Double Helix: A Personal Account of the Discovery of the Structure of DNA, James D. Watson. Touchstone, 2001. ISBN: 9780743216302.
If Watson were to tire of molecular biology, he could become a great mystery writer, on the level of Arthur Conan Doyle. His account of the discovery of the structure of DNA exposes a level of competition, politics, deception, sexism, and mystery that you would expect to find in a board room, not in a scientific community.
Management and Leadership
Out of the Crisis, 2nd edition, W. Edwards Deming. MIT Press, 1986. ISBN: 9780262541152.
MacArthur brought Deming to Japan after World War II. He transformed Japan from a maker of junk into the industrial envy of the world. The Japanese Union of Scientists and Engineers has awarded the Deming Prize annually for the past 60 years or so in his honor. In his book, he emphasizes that a good leader makes it clear to each person in his/her organization that that person is valued, that his/her work is valued, and his/her work makes a difference. Annual reviews are not for grading, they are for identifying what is done well and where improvement would have the most impact.
Superminds, Thomas M. Malone. Little, Brown, 2018. ISBN: 9780316349130.
How to put minds together, both those that are dry inside and those that are wet.
Finance and How Markets Work
Adaptive Markets: Financial Evolution at the Speed of Thought, Andrew Lo. Princeton University Press, 2019. ISBN: 9780691191362.
Lo tells great stories about how stories push financial markets around.
Deportment
A Message to Garcia, Elbert Hubbard. Independently published, 2019. ISBN: 9781794273726.
Lieutenant Rowan got the message to Garcia. You should too.
Lord Chesterfield's Letters, Lord Chesterfield. Oxford World's Classics, 2008. ISBN: 9780199554843.
Chesterfield wrote his letters in the first half of the eighteenth century, but much of his advice remains valuable. My grandfather gave me a copy in 1963, with particular parts underlined for my benefit.
Where We Come From
Masters of the Planet: The Search for Our Human Origins, Ian Tattersall. St. Martin's Griffin, 2013. ISBN: 9781137278302.
We didn't amount to much before 70,000 years ago. Tattersall explains that we became symbolic.
Why Only Us: Language and Evolution, reprint edition, Robert C. Berwick and Noam Chomsky. MIT Press, 2017. ISBN: 9780262533492.
Berwick and Chomsky refine Tattersall by explaining that we got an operation, merge, evidently missing in other species. Merge matters, in my view, because it enables story composition.
Speaking
You cannot actually put these on a bookshelf, but they are useful nevertheless:
How to Speak, Patrick Henry Winston.
A talk given annually at MIT. Some attend multiple times. The record so far is said to be greater than 10.
"Give Me Liberty or Give Me Death," Patrick Henry.
If you are thinking of starting a revolution, read Henry's speech and adapt it to your purpose.