It's a rare occasion that companies provide leadership training before you become a manager. A few days or weeks after what was probably one of the happiest days in your recent memory, the day you were offered a position outside of the individual contributor track, you find yourself with a million questions. You feel that you were tricked into signing something without reading the fine print.
That feeling you're experiencing isn't new, it's just that you've all but forgotten it. It's not knowing what you're supposed to do. It's being clueless. Because if you think years of writing software trained you to become a manager, research states the contrary. But it's not the end of the world. Even though your company most likely doesn't understand the need for formal management training, there is a plethora of information available to you that will make your job easier, and maybe even enjoyable.
When I became a manager I did what I typically do when faced with a challenge I know almost nothing about: I started reading. I've read a lot of books, some were good, a few of them were amazing. All of them shaped the way I do my job, and so I thought I would share them for other aspiring or active managers out there.
I've curated this list based on several factors:
- The books should cover a broad set of engineering management and leadership topics. It's easy to find overlapping books. It is much harder to find a diversity of information when you're very new to leadership.
- They should be written in different eras. The software industry is constantly evolving. It doesn't make sense to only read about what was happening in the 1980s or 90s.
- Reading order matters a lot. Some books are more specialized than others. The information provided can be thought of as layers that stack on top of each other. If you're inexperienced, you may start in the middle or the end, and that will basically ruin other books for you.
- Finally, I put a hard limit of 7, just because I think this list is enough to build a foundation layer on top of which you can continue reading and maybe even doing your own research further on.
But enough introduction, let's see the list :)
This should be mandatory reading for everyone. Period. No, not just everyone in software, everyone working in a private company should read this book. It's amazing to me how pretty much all of the problems that people deal with it on a daily basis have already been solved. In the 1980s. If you read just one book from this list, let it be this one.
Soon after you make the switch from the individual contributor track to the leadership track you will ask yourself a basic question.
How do I measure my own success?
You used to be able to answer that easily. Now that you're writing code less and less, and dealing with team dynamics and people problems, how will you or your boss measure your progress and success? This book provides a now universally accepted answer: you are measured through the success of the people reporting to you. That is to say, if your team is successful, then you're successful. I'm over-simplifying of course but that was my biggest take away from this book.
There are more insightful bits of information such as a walk-through of a production pipeline, how to run meetings, or how to conduct one on ones. This is a classic book that everyone should read even if they're not interested in leadership roles. It's that good.
I will say though that this book was written a long time ago. The impression I got was that leaders from that age were more authoritative than what you see in companies these days. This is not a critique, it's a fair warning. You may read a few chapters and conclude that there's no way anyone could get away with doing that in a company. There's a certain nuance to the leadership style described in this book and it is important to understand it.
An engineering manager's job is to ensure their team has everything it needs to succeed. This means managing the interaction between multiple groups of people towards an agreeable outcome.
If you've ever tried to convince a friend to move from WhatsApp to Telegram and failed, you've made an attempt at exerting influence. You'll need to do that basically every day, and in my experience, this is a very hard skill to learn. It takes a lot of practice, and there's really no sandbox mode in which you can fail and it'll be OK. You will try to talk to someone at some point into doing something, and you will fail, and you or your team will suffer for it.
This book is the definitive guide on how to approach the problem scientifically. A lot of managers seem to think they don't need to learn how to influence others, particularly their direct reports, as rank is the ultimate influencer. Thinking that will keep you from ever becoming a great leader, in my opinion. Yes, you will probably overrule someone at some point and it will feel terrific while you do it. But if that person ends up hating you for it, you've just lost their trust and you will see the consequences of that later on.
This is another classic textbook that I wish everyone in software would read. If you're currently in a company who's agile and are struggling with unproductive meetings, poor quality code, team members that can't get along with each other, or stakeholders who push you to leave the office late at night, you will find at least one solution within this book. It's also a good leadership book as it describes, in what is probably my favorite chapter, a list of things you definitely should not do if you want to have a great team. I still refer to that chapter from time to time, it's just really good and insightful.
I loved this book for its humor and insights into some of the biggest tech companies' cultures. It doesn't feel like a textbook compared to the others on this list, but that's what makes it a great fit.
You need to understand that leaders are still human, they're going to screw up, and the end result may be tragic or hilarious. Or both. That's a very important lesson to learn, one that took me the longest time, to be honest.
It's very easy to get caught up in theory while trying to learn how to be a leader. But reality often is so insane that no book can offer you the solution you need. You will end up in situations where you will do everything by the book, and people will still be unhappy. And that's OK. The stories from Managing Humans will help you understand that.
What makes this book awesome is that it offers a clear and simple description of your responsibilities and goals at every step in the leadership ladder. Most companies don't even have that information for their own leadership track.
It starts by describing what an entry-level leader should focus on, such as mentoring junior developers. It moves on to engineering managers, senior managers, and even covers what a VP of software should do. I personally have always wondered what a day in a VP's shoes looks like, and if you have as well, this book is for you.
Beyond just taming your curiosity of what the upper echelons look like, I love this book because it is so realistic. There's no utopian view of teams and processes here. It's all ground in the experience of the author. That makes the information within highly applicable in your work environment.
I initially didn't want to read this after I found it, but I'm glad I changed my mind about it. It's basically a short story about a manager who is very good at his job, particularly in one area.
I won't spoil it for you. The information you get out of this story isn't particularly innovative. There are other books that dive into its topic in more detail. But there's something really satisfying about it that I can't really explain. It's like a GitHub gist that solves a problem in under 100 lines of code.
You can be dismissive of it — there's no way it could be that simple, right? Or you can read through it carefully and appreciate its simplicity, knowing that it's not a generalized solution, but still good enough that it's worth having in your toolbox. It is entirely possible you'll read this book and think I'm exaggerating, but hey, it's my list ;)
I can count to 7 just fine, but I really wanted to offer this book as sort of a special addition to my list. I wouldn't say it's mandatory reading. Once you've gone through all the books above, you should pick this up for a very striking alternative view.
Basically, Radical Candor is a framework on how to relate to people. It's not really related to software development. You can apply this anywhere, with your friends, with your family, it's frankly very abstract in that regard.
The author, Kim Scott, has worked both at Google and Apple. She recalls some of her experiences while working there. I found those chapters to be extremely enjoyable, but do take them with a grain of salt. Some of the more recent reports in the media directly contradict some stories from this book. This is why I'm hesitant to recommend it to everyone.
The framework itself makes sense but it's so hard to actually put in practice. I know that's not the author's fault. I wish the world would work in the way she describes, but I don't think it ever will. Nonetheless striving to achieve even 50% of Radical Candor will make you a better leader. If you have the stomach for 100% then I'd like to meet you in person.
Is that it?
This list is a solid foundation for newbie managers or people who are thinking of becoming team leads or managers. There is so much more to learn. I would've appreciated a simple and short list like this myself when I made the step towards leadership. Hopefully you do as well.