Folks starting out on their management career or thinking about higher-level engineering roles such as Staff have a daunting task ahead of them. While much of the specifics vary company by company, there’s some fundamentals that tend to stay the same. Luckily “there have been whole books written about this stuff”! Even more luckily I’ve compiled a big list of books I’ve found useful that made it into a sort of required reading list for folks in my group. I’m sharing it now with this wider audience.
Reading is only part of learning. You should also practice to develop expertise as an EM or IC. If you want a workplace implementing many of the great ideas in these books, Bolt is hiring!
The list itself focuses on topics of leadership, management, startups, or product management. Everything except technical topics! It is both classics in the field of technology leadership, or very relevant and more recent books. Furthermore, the material and books are selected to cover as much distinct material as possible relevant to the audience.
General Leadership Reading.
Every manager should take a good lesson from these books. They describe the job in many ways. Even non-managers have a lot to learn, since understanding the constraints of your manager helps you be a better partner to them.
- First Time Manager - a very broad introduction to management in modern corporations. It has a natural focus on “line management”. Crucially it is not a “technology management” book, hence you can get a broader picture of management.
- The Manager’s Path - the classic of engineering management. It describes the role of engineering managers, the expectation and reality of it all the way from line managers and up to VPs and CTOs. It’s useful not just as a tool for the present, but also for understanding your future and what a career in management can offer.
- How To Win Friends And Influence People - yes, it’s corny but it is a classic for everybody for a reason. The core message is about kindness in communication and a focus on understanding the other’s wants and needs. Whenever you see an EM or IC sabotaging themselves and their team by being nasty on Slack, this book would help them.
- Deep Work - this is a book on the importance and practice of “deep work” - the skill of focusing for long periods of time on a cognitively demanding task. Essential for high-level ICs of all sorts. But very important for EMs too - both to understand their IC counterpart and their needs , but also because a big chunk of EM work still is like that!
L1 Managers Reading.
Managers of a single team should take a special look at these titles.
- Peopleware - teams are the unit of building software, and happy and gelled teams are the unit of building software effectively. This book is all about that, plus a lot more about interviewing, development processes, etc.
- Managing Humans - anecdotes and war stories from the author’s long and storied career. A lot of tactical lessons here, but all well worth having in your arsenal.
- Help Them Grow Or Watch Them Go - a very short book on career conversations with your teammates, and how to be active and proactive in their career journeys.
- Radical Candor - a book about providing (and receiving) feedback in a constructive way. Especially the difficult one. A constant of the leader’s life! It also teaches you not to fall into the trap of ruinous empathy or the trap of simply being a dick!
- Crucial Conversations - crucial conversations are discussions with high-stakes and differing views on the right outcomes. A constant occurrence for leaders! This book teaches one how to navigate these difficult conversations in an effective way, achieve win-win solutions for everyone.
L2 Managers Reading
Managers of multiple teams and of other managers should take a special look at these titles, besides the L1 reading section.
- High Output Management - the granddaddy of technology management and leadership! OKRs come from here, manager-as-coach too, as well as the most succinct definition of what a manager does I’ve yet to find - “the output of a manager is the sum output of their team”. Looks both at lower -level management, but it shines at the higher-level aspects.
- The Effective Executive - a classic of the business world. Executives are the people who make decisions. In most tech organisations, this means a helluva lot more people than “the executive team”. Almost everyone in engineering is included.
- An Elegant Puzzle - a very new addition. This book looks at problems and solutions for leaders of high-growth tech scale-ups. It speaks about structuring organizations , building hiring pipelines, the product-vs-platform split, scaling systems and the organizations that build them , etc. All backed by XP from Digg, Uber, and Stripe!
- Staff Engineer - a very new addition, but one that’s on its way to becoming a classic. Mostly because it is the only book that deals with the role and expectations around being a high-level engineer! Read this to understand how to grow SSWEs up to Staff and beyond, and how to engage with Staff+ engineers in general.
- Team Topologies - a book about structuring organizations, with a focus on building the right kind of teams that interact in the right kinds of ways.
- Accelerate - some teams release software every day, or even multiple times per hour, at very high quality. Some others release buggy software once a year. This book outlines why the former approach is the way that leads to good things ranging from better company outcomes to more engaged workforces.
High-level engineers should take a special look at these titles.
- Deep Work - this is a book on the importance and practice of “deep work” - the skill of focusing for long periods of time on a cognitively demanding task. Essential for high-level ICs of all sorts. But very important for EMs too both to understand their IC counterpart and their needs, but also because a big chunk of EM work still is like that!
- Staff Engineer - a very new addition, but one that’s on its way to becoming a classic. Mostly because it is the only book that deals with the role and expectations around being a high-level engineer! You need to read this to understand what the organization is expecting of you - if not now (because we’re in a fuzzy state), then in the coming years!
- The Manager’s Path - the classic of engineering management. It describes the role of engineering managers, the expectation and reality of it all the way from line managers and up to VPs and CTOs. If you want to partner successfully with your manager, director, or VP, you need to get into their headspace and way of understanding the world.
- The Effective Executive - a classic of the business world. Executives are the people who make decisions. Which absolutely includes higher-level engineers.
Basic Startup Reading
These are books that have been influential to generations of entrepreneurs. Understanding the startup or scaleup mindset is thus very important for everyone taking on a more central role in such organisations. At larger product companies or project ones your mileage may vary.
- Zero To One - a look at building startups courtesy of Peter Thiel.
- The Hard Thing About Hard Things - another look at building startups courtesy of Ben Horowitz. Covers scaling businesses too!
- No Rules Rules - describes the culture and learnings around ownership and performance from Netflix. One of my faves.
Finally, there’s a set of books which look at the wider world in which engineering teams work.
- Inspired - a book on Product Management. You should have an understanding of the role of a product manager, what to expect and what not to expect from them.
- Dictator’s Handbook - a look at how power works within organisations. The main focus is on states, but the lessons are applicable very much to companies too.
- Why Nations Fail - again a political science book. Good countries have a lot in common with good companies - inclusive institutions and many people at the helm guiding the ship.
- The Prince - I especially like the School of Life interpretation. The world is what it is, and effecting change requires knowing how to play a game you might not agree with.