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Business Books for Technical Leaders

I get a lot of questions like, "You seem to know a lot about business for a technical CTO. How?" and "I'd like to be a CTO someday. Do you have any tips?" First and foremost, a CTO is a business-focused role. You must be able to do whatever the business requires most at any given moment, whether that's coding, technical architecture, hiring, raising money, selling, conducting a layoff, leading Product, being a stand-in COO, or otherwise.  One of my common responses to these questions is, "Read and be curious!" But read what, exactly? Since I'm a fan of scalable communication, I'm documenting my recommended reading list here for public consumption.  This list is current as of March 2024, and I plan on updating it ~yearly. Top Ten Business Books (Must Read) Ten might seem like a lot of books, but an executive should be reading 10-20 books a year, and when you multiply that by a 10-20 year career to become an executive, you'll have read hu