Leadership Books.

Books stacked on a table, in front of a skyline


Leadership is its own craft, not simply an extension of other crafts. While every situation will provide a unique combination of challenges, there are commonalities that every leader will struggle through. These books provide a good starting point.

One caveat, while High Output Management is a classic, some of it is starting to feel a little dated, so read it with that in mind, and take away parts that feel authentic to you. For technical managers, we especially recommend the more recent The Manager’s Path.

Building teams and organizations

Do you want to be more of a golf team or a basketball team? A golf team is a collection of people who each play their own game, then add their scores together at the end. On a basketball team, everyone plays the same game. They may have different roles, but they work in concert, utilizing each other’s strengths, to achieve an outcome.

The latter is usually what people imagine when they think about high-performing teams at work, but building teams like this is hard. These books touch on theory while offering a bunch of practical advice.

Managing scale and growth

Some things get easier as your company gets bigger, but a lot of things get significantly harder. These books from Reid Hoffman, Ben Horowitz, and Bob Sutton are packed with stories and actionable advice on how to scale teams.

The human side of work

It may sound obvious, but companies are made up of people, and therefore leaders should seek to understand the needs and drives of themselves and others. There’s a wealth of pop-psychology books out there, but I’ve found these helpful when looking at motivation, habits, and mental blocks.

The future of work

Modern companies are complex networks, a far cry from the production lines of the industrial revolution. Yet many organizations use practices carried over from the scientific management of the last century. These three books will help you understand this changing nature of work and provide alternative approaches to organizing your people.

The business side of business

As a leader of any function, it’s important to have a baseline understanding of business dynamics. We feel these books provided a good foundation, though as Martin Casado notes, many of today’s companies never cross the chasm and the messy middle is the new normal.

Copyright © 2024 Daniel Pupius.