Ask HN: What are the most inspiring books on leadership?

How to Win Friends and Influence People (but buy an edition printed before Carnegie died; more recent versions have been rewritten by other people)

Great book. There's also a good BBC interview with Warren Buffett talking about the original Dale Carnegie courses.

"Bismarck: A Life" by J. Steinberg. An object lesson in overweening use of power and personality. But lessons for effective leadership nevertheless.

"The Score takes Care of Itself" - Bill Walsh

Jack Dorsey talked about it in Startup School and I highly recommend it as well.

Herbert Simon's Models of My Life is in general interesting and has some very good sections on leadership, mostly in the research and academic world. I don't know that I would call it inspiring.

The Endurance: Shackleton's Legendary Antarctic Expedition

Change by Design by Tim Brown