Educate yourself — A Booklist
This is the book list I recommend for tech folks like me that transitioned to management. My background is system administration and programming but I always loved to understand how executives and companies came to be. If you read all that, consider you got grade A on my mind's MBA.
More than that, this is a journey to understand how to get prepared when opportunities come knocking. My advice here is think big, think like a CEO. It is free and you got nothing to lose. Even when you end up kicking stones laid off.
Most of these books I re-read each 2 or 3 years and always find something new to absorb. You gotta read them before May 2016. Beside these books you gotta watch Office Space the movie.
The links below are associate links by Amazon. Feel free to not use them to buy a book if you got interested. Proceedings of this account are going to fund new books.
High Output Management
A classic on managing smart people by former Intel CEO Andy Groove. Basically you gotta find references to this book around blog posts, books on management and even biographies. Beyond helping to create the semi conductor industry on USA and advising people like Steve Jobs he grouped a practical set of practices and examples for a pragmatic operation oriented executive. The extensive part on one-to-ones shaped many articles and company cultures around the world.
The Hard Things About Hard Things
Following closely High Output Management I find this book by Netscape founder and Investor Ben Horowitz a great reference on being a C level executive (that I could relate if I was a C level executive on a real company).
The chapters on war/peace time executives and the energy on how he started a new company and almost got dropped from the stock exchange is great. Also, each chapter has a gangsta rap quote, how can that be bad ?
Creativity Inc.
Starts slow, but builds up on a nice narrative of Pixel and how it found a way to replicate and scale its creative process. I read it because I read the next book first and it had a lot of references about John Lasseter. His account on the pressure for revenue, growth and being acquired is detailed and mesmerising.
Becoming Steve Jobs
Same old drama about Steve Jobs in the beginning, like how he was such a hard ball, a**hole and so on. I figure out people get labelled like this and you end up having to endure the drama. Steve is not my personal hero but I can understand he got pissed with people from time to time. The good part there is about how he got back to Apple and started organising his team and mainly how he acquired Pixar and sold it to Disney. No CEO lessons here beyond "do your job, screw the lazy ass, find great people to work with etc etc" but if you combine this part with "Creativity Inc" part on how they were bought by Steve Jobs it gets really informative.
Different
Praised as the best part of a Harvard MBA, if there is something possibly not boring as hell as a MBA, Youngme Moon is one of the most praised and awarded professors. This book is on Marketing Strategy and more generally on how the world works. That broad. For a tech background guy like me, it is eye opening (and not dull like other marketing books).
Architecture and Patterns for IT Service Management, Resource Planning, and Governance: Making Shoes for the Cobbler’s Children, Second Edition
This book and the next were referred by a former boss and mentor. Beyond the content, which is very interesting and detailed, this book is a reference about where things like ITIL and COBIT were inferred by the gracious people that built the original methodologies content. It makes you thing on how to work on Web Operations as a Delivery team and not only a group of technical alarm watchers/system administrators. It helped me go through organising and improving a huge team by focusing on service.
Making things happen — Mastering Project Management
All you need to know, no PMI/PMP stuff on projects. This is more like a reference book but can work as the cure for Agile. Guidelines that helped me from software projects to infrastructure projects.
Drift into Failure
Dr Sidney Dekker wrote this masterpiece on complex systems populated with examples illustrating what we know and it is hard to admit: there is no human error. Either people don't know how to do something or don't want to do something. Getting them between complex machines, risky processes and underpressure wont help.
Command and Control: Nuclear Weapons, the Damascus Accident, and the Illusion of Safety
Another volume on how to relate control to perception. It comes from the history on how old trains worked to a complete history on nuclear power and structure. It examines accidents, types of reactors and a bit about how the nuclear bomb came to be.
The Black Swan
Nassin Taleb wrote this and I really have nothing else to add. Very dense book, the kind that you get back from time to time to digest.
Project Phoenix — A novel about IT
This book is hard for people that had to take any kind of operations and delivery area and build it back as a productive team. The last part is a bit romantic and unreal to me, more like selling the DevOps idea but it is a small price to pay if we take in account that it made me cringe more than watching The Office about 10 years ago.