Reading for new leads

These are books that I have used in my own development as a leader and that I recommend to all new leads on my team. Some are situation-specific (e.g. navigating the transition period) but many are books that I’ve returned to many times. The intent is to share what has worked for me.

1. The First 90 Days

A handbook for navigating your transition to a new role. Key insights include how to identify and approach the specific environment you’re entering, generating momentum through early wins, and negotiating expectations.

The best time to start reading this is at least 30 days before you change roles.

2. The Five Dysfunctions of a Team

A light read with deep insights into team dynamics. The first half is a narrative form, followed by a more direct outline of the key concepts. The key concept is that trust is the foundational building block of a high-functioning team.

Look up the Five Dysfunctions pyramid for a quick summary.

3. The Manager’s Path

The closest thing to a handbook for leading in a technical environment (though many insights are useful for non-technical areas). The book covers every level of development, from individual contributor to CTO.

Skip to the chapter that best fits your current or upcoming situation.

4. Fierce Conversations

An inevitable part of leading a team is navigating difficult conversations. This book gives you some useful strategies to handle them skillfully. It’s more helpful and engaging than the often recommended Crucial Conversations.

5. High Output Management

Getting into the theoretical end of things, HOM dives deep into a few key areas of leadership. It covers both managing people as well as organizations and strategy. Key concepts include high and low leverage and an introduction to the Theory of Constraints.

Don’t let the first chapter deter you – skip it if needed, because the rest is gold.

6. The Effective Executive

Even more meta, this book is useful for any knowledge worker. It will give you insights and strategies to be more effective, from managing yourself, to your team, to an organization.

Drucker has influenced a huge number of highly successful people – this is a book to be revisited regularly and kept close at hand.

7. Team of Teams

Particularly useful if you work in a highly complex, rapidly changing environment. Key insights include leveraging situational awareness, the importance of connections across teams, and the value of trust and adversity in bringing on someone new to a team.

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