I find myself reading in two very different modes. In one mode, I'm trying to learn something specific typically to unblock me from another task. I might need to know details about a garbage collector or need to know how to write a small compiler. In other cases I'm getting exposed to something entirely new that I know nothing about (e.g lead scoring or purchasing) and need a crash course. It's hard to make general recommendations for this kind of reading. So much is up to the context of your particular topic.
In another mode, I'm trying to broaden my knowledge more generally. I can illuminate gaps in what I know and challenge biases that rarely get checked. In order for this to work, I have to free myself a bit from solving a particular problem. If my reading is a bit more aimless, I'm more likely to get a broader view.
The biggest mistake I made in my youth was avoiding contradiction and ambiguity. When I read something, I was focused on whether I agreed with it or not. I eventually found this incredibly limiting. Lots of interesting ideas are imperfect. At this point, I try to focus on absorbing and understanding what I read and give myself the freedom to not worry about agreeing or disagreeing, at least for a while.
I keep saying reading, but if I am being honest, most of my consumption comes via audiobooks now. I listen to them while I do dishes, walk, drive, or workout. Ok, for the heavy part of the workout I switch to some heavy stuff, but warm-up is all audiobook. This isn't optimal, but it's how I get it done. In many cases, I'll go back through and buy the actual book if it's useful. Whether reading or listening, some ideas take a few passes. The point is, however you get yourself able to read, do it. Perfection isn't worth it.
- A Philosophy of Software Design - John Ousterhout - An efficient set of cogent opinions on software design
- Designing Data-Intensive Applications - Martin Kleppmann - A distributed systems primer for our times
- Release It! - Michael T. Nygard - The book that you'll consistently wish you had read more closely when you get paged at 2 am
- The Five Dysfunctions of a Team - Patrick Lencioni - It's narrative weirdness and questionable bonafides aside, there's a clear eyed view of dysfunction that will leave you wondering whether you are the problem
- Measure What Matters - John Doerr - It's a bit of a tail wagging the dog thing because it's the OKR book, but this is good entry into thinking about how organizations operate at a macro level
- The Field Guide to Understanding 'Human Error' - Sidney Dekker - An acidic take on how organizations blame individuals
- The Manager's Path - Camille Fournier - A very practical view of what it means to move from the code to management
- An Elegant Puzzle - Will Larson - Not sure how this will hold up over time, but certainly seizes on some specific zeitgeist
- Extreme Ownership - Jocko Willink and Leif Babin - A clear-eyed view of leadership from Navy Seals. This has stories from the Iraq War that are effective in showing their points but can distract a lot of folks for personal reasons. Turn the Ship Around is a good alternative though I think it's a tad more meandering.
- The First 90 Days - Michael D. Watkins - I have vivid memories of reading this the day before my first day at CircleCI... Good specific advice about setting the tone of your work interactions
- Good Strategy Bad Strategy - Richard Rumelt - A bit padded even by business book standards, but vicious in it's takedown of fuzzy thinking and backslapping
- The Innovator's Dilemma - Clayton Christensen - The book that should have been a tweet storm had twitter been invented yet, but it's a shockingly dead-on look at what kills big companies