[dublin]

Some good suggestions (and a couple I'll have to read...) I'd add the following:

8. "The Mythical Man-Month" by Fred Brooks (still, IMO, one of the best management books ever, esp. for software and product development.)

9. Boyd: The Fighter Pilot Who Changed the Art of War by Robert Coram (OODA is the true core of agile thinking, and it works pretty much everywhere.)

For software and computers specifically, add:

10. Computer Lib/Dream Machines by Ted Nelson (Impossible to categorize - it's a hypertext book for crying out loud - but browsing it can change your thinking.)

11. The Soul of a New Machine by Tracy Kidder. (Good for new products in general.)

And for general management and leadership inspiration, two great autobiographies:

12. Mover of Men and Mountains, by R.G. Le Tourneau.

13. Rickenbacker, by Eddie Rickenbacker.

[goopthink]

Some good additions there, some I’ll need to check out. I really liked the Boyd book when I read it, but I would probably recommend his papers/reports or some of the more short form things written about him to get to the point faster (RibbonFarm/Venkatesh Rao was how I was introduced). That said, I did learn a lot about navigating bureaucracy (perhaps bullheadedly).

On that note, I would also add another book about organizational psychology - how people game incentives, how cya evolved, how people focus on short term thinking over long term investments, problems common across big businesses, written by a sociologist embedded for a few years in a corporation, but I can’t for the life of me remember it.

But also:

The Secrets of Consulting” by Gerald Weinberg on generally thinking through ‘solutionizing’.

“Systemantics” by John Galt as a short and fun intro to applied systems thinking and cascading effects.

“We Need to Talk” by Celeste Headlee on how to have difficult conversations.

“Never Split the difference” on handling and understanding negotiations both up and down the chain.