A few people have asked, so here it is. I haven't read every book out there, so please tweet at me if I'm missing good ones!
Peopleware by Tom DeMarko and Timothy Lister.
This is the classic. Originally published in 1987, the premise is that most software project problems are sociological, not technological. And since human nature is slow to change, this book is just as relevant as when it was published. It's been updated several times, most recently in 2013, and is wonderfully written.
The Manager's Path, by Camille Fournier.
This practical guide contains all the information one needs to introduce structure and process to a company as it evolves over time. First published in 2017, I wish I could have read this much earlier in my career, as it gives the clearest picture of the work of engineering management.
Behind Closed Doors: Secrets of Great Management, by Johanna Rothman and Esther Derby.
There's nothing here specifically about engineering, but the advice and approaches in this easily digestable book made a big impact on me. Right away I could tell which of my previous managers had read this book, and which hadn't. It's a sanity check on typical management practices, and provides solid reasonings and examples throughout. It draws no distinction between management and leadership, and the title comes from how good management is often not seen because it happens behind closed doors.
- Managing Humans, by Michael Lopp.
This is so much more than "biting and humorous tales". This hefty book is chock-full of perspectives, suggestions, warnings, and disclaimers. Michael respects professionals in all their weirdness, perhaps because he's a bit of a weirdo himself. As individual anecdotes, the chapters are interesting, informative, and frequently funny. As a whole, Michael presents a powerful professional mindset, one that I endeavor to take in.
I'll be re-reading these for as long as I'm working with other people, and I recommend them frequently. Here are a couple more that I've read recently and thought had good parts.
How F*cked Up is your management by Johnathan Nightingale and Melissa Nightingale.
I'm back and forth with this book. Perhaps they could have benefitted from more editing. But the fact is, I keep coming back. It's very broad collection of relevant situations, especially if you've spent time in digital organizations or startups. Many of the stories are unique, in that I haven't read them elsewhere, and also in that they happen to resonate with my own experiences.
Talking with Tech Leads by Patrick Kua.
I was excited to find this book, since I had not seen something like it before. I remembered early on in my career being curious about the elusory Tech Lead role, and wishing to get in on the secrets. Perhaps the format was a little too rigid, or the insights a little too mundane, but this book didn't completely fulfill my hopes. It has it moments, especially the conversations with more seasoned engineers -- those who decided to stay in the role of Tech Lead, rather than move into management or architecture.