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 well before you change roles.

2. The Five Dysfunctions of a Team

A light read with deep insights into team dynamics. The book is helpful for understanding what makes a healthy and effective team, as well as troubleshooting team issues. 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.

I recommend this book for new leaders because I’ve found trust to play an essential role in teams. Understanding the dynamics and health of your team is just as important as developing your individual skills as a leader, since your job is to achieve results through other people.

Look up the Five Dysfunctions pyramid for a quick summary.

3. Leadership & Self-Deception

One of the most important skills to cultivate is self-awareness. This book is a narrative, similar to The Five Dysfunctions, and uncovers what it means to really see other people, yourself, and the impact you have on others. I read this book more recently, but I wish I had come across it earlier in my career.

4. Fierce Conversations

An inevitable part of leading a team is having difficult conversations. This book gives you some useful strategies to handle them skillfully. As someone who tends to maintain harmony and avoid conflict, I found this book incredibly helpful early on to get over the initial learning curve and discomfort. Crucial Conversations is also helpful, but I found Fierce Conversations much more down to earth and engaging.

Personally, I would start with Fierce Conversations and then move to Radical Candor, as I find the former provides more foundational skills that you can then build upon.

5. High Output Management

High Output Management is best all-round leadership book. It includes an introduction to understanding operations (throughput, constraints, etc), delegation, leverage, strategy and more. This is the book that I come back to most often, even if it’s just reviewing a specific chapter.

The first chapter can be a little dry, though the lessons in it are incredibly important. Skip it if you need to, because the rest is gold.

6. 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 with a bit of translation). The book covers every level of development, from individual contributor to CTO.

I recommend this book most often to people who are leading other leads for the first time, as it’s the only one I’ve found that addresses this topic head on.

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

7. The Effective Executive

The Effective Executive is useful for any knowledge worker, but particularly important for leaders. It will give you insights and strategies to be more effective, to understand and manage your time, and to make sure you’re having the most impact that you can have in your role.

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

8. 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.

I recommend this to new leaders because leading in a complex and ever-changing environment requires new ways of thinking and more humility. This is a good starting point for leaders to leave the linear, old school ways of managing that they likely had experience with in school or previous jobs.

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