I've been asked many times for book recommendations, especially by technologists who are moving into more senior management positions. It has come up a lot recently and since I usually trot out the same five core titles as starters, I thought it worth posting my thoughts including the reasons.
Opening disclaimer - I am not sponsored by or affiliated with any of the authors or publishers, or with Amazon - other book vendors are available. However if you'd like me to read your book for money, then do get in touch...
My favoured books tend away from direct "this is how you do…" books and towards those which give new viewpoints and (different?) frameworks for thinking. With that in mind, five books I recommend coming up.
Two good starters
The first two are great foundation books. They cover some core management and strategy concepts, while being very readable.
Leadership: Plain and Simple
This is a short book, describing the simple but easy to overlook steps involved in successfully making change happen in an organisation - have a vision, then get people on board, then look to deliver it. It is framed around "Future, Engage, Deliver" and describes load of examples and pitfalls. I actually read the first edition of this (I think this is the second?) but I assume it still covers the same ground.
The underlying points are great foundational thinking, and the detail is so easily forgotten when things get difficult, deadlines hit or we get lost in the weeds. It's a short read and well worth cementing in one's memory.
Good Strategy/Bad Strategy: The difference and why it matters
A much longer book about what makes good strategy, what makes bad strategy, and why "bad" is distinctly different from just "no strategy". The author, Richard Rumelt, is a huge name in the academic strategy world and can name-drop in a frankly ridiculous way. Again, this is very easy and enjoyable to read. For me, it solidified a lot of vague notions in my mind and it was highly liberating to see some of the things that seemed wrong by my own observation pilloried by someone with the expertise, experience and vocabulary to describe them properly.
The killer line for me was describing a particular form of poorly thought out bad strategy as like a team captain starting a game by telling the team "our strategy is to win".
I do warn people that reading this book will start to turn you into a strategy snob, similar to people who get snooty about coffee or audio when they start to learn about it properly, but personally I take that as a sign of a good book rather than a bad thing. It opens eyes and the number of "oh of course" moments are measured per page, not per chapter. In particular it has made me much more careful about using the word "strategy" in its more colloquial form (i.e. meaning "anything coming up").
My favourite book
The Five Laws to Foresee the Future. 12 Paradigm Shifts That Will Happen in the Future of Human Society
This is probably my favourite "management" book, but be warned it is REALLY tiring to read. To my inexpert eye, it reads like poetry written in a foreign language, translated to English more or less directly without any of the rewording to embrace language idioms you might expect. The author is a Japanese businessman and philosopher so I might not be too far from correct.
However. It is a brilliant, eye-opening view of using dialectic thinking to understand patterns in business, market and societal change. Taking it to the next step, the thinking can be used to consider what might be coming next which makes it invaluable if one is in a role where one needs to anticipate future trends and directions. I am a mathematician, so I like to analyse patterns in the world around us and this provides an excellent framework for doing that. More than anything, it helped me think differently about what I was seeing and that is always worth the price of admission.
This is the book I return to more than any other in this field, and the one that keeps granting new insights as I read it differently. Definitely a book to read in small chunks, with lots of reflection time in between.
Three management / leadership books are enough to be getting on with. The other two are about understanding people and yourself - a too-often overlooked aspect of leadership.
Depressive Illness: The Curse Of The Strong
If you are responsible for people, just as you're going to come across someone with a physical ailment (whether it's a common cold or something much worse), you are going to come across someone with some kind mental health issue. It is essential as a manager that you have some idea what this means, and what you can do about it. It is also important to understand how your actions can create an environment which negatively impacts your colleagues and reports.
This book focuses on clinical depression, which is depression as a physical ailment. It is written by a leading consultant psychiatrist, and highly recommended by folk in the mental health professions (not just me). There is a lot here which helps better understand depression and is well worth reflecting on both for the self, and for what it means for our behaviour to those for whom we have responsibility. If it helps a manager spot one person who is heading in a bad direction and take action, it's worth it.
Finally, we have The Enchiridion. Where the previous book was mostly about understanding others, this is more about self-reflection. It is a classical Greek text written about Stoicism and is a great read to understand different ways of thinking - especially when it comes to how people can draw satisfaction out of the world around them. This is very important for technologists stepping away from tech into leadership as we all go through the same slump where we wonder what on earth we're doing and whether we'll ever be happy at work again. "Where do I get my energy from?" is a very difficult question to answer and one I've written about many times over the years. This book gives one way of finding an answer.
It is not the easiest read, but potentially a different way of thinking and definitely easier than the third book.
Picking the Right Transition Strategy
As a bonus, there is this (free) Harvard Business Review article which is about assessing a business environment and choosing the right leadership strategy. It is another model for focusing thinking, and is worth having in the back of one's mind both for moving to a new role and for assessing the state of the current working environment.
And that is it. Now I have a blog post next time someone is looking for a recommended reading list. Hopefully there is something useful here.