The 3 Worst Books for New Leaders

Jul 16, 2021 | Blog

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The 3 Worst Books for New Leaders

Be Wary When You Read These Titles

When you pursue a career in leadership, well-intentioned leaders and mentors often want to help. It’s common for those who came before you to share what was recommended to them, which is great. Philosophies have changed over time, though, and some of them are more harmful than helpful. There are three books I’ve seen consistently suggested for new leaders throughout my career, and while they can be helpful, it’s not for the reasons you might think.

Here are three books I DON’T recommend if you want to become a great leader:

How to Win Friends and Influence People – Dale Carnegie:

This book is the least dangerous of the three, but I wouldn’t consider its teachings positive. While it’s true that navigating people takes skill, this book does what it says: it teaches you to “win” and “influence,” and it does so with manipulation tactics. How to Win Friends and Influence People has been incredibly popular over the years, so many leaders you encounter come from this line of thinking. While I don’t suggest you apply the lessons from this book, read it to see when people are applying it against you.

The Art of War – Sun Tzu:

Again, this is not the worst book on this list, but also I don’t think it’s a great book for leaders. At its core, it’s military theater being sold to leaders with the idea that it helps them maneuver their way through corporate life. If you’re following the path of the servant leader, this is not the treatise on that. However, leaders from military backgrounds often subscribe to this philosophy, and it’s quoted more than almost any other book on leadership. Different situations call for different tactics, and it’s good to know them, so read this book and put it in your utility belt, Batman.

The Prince – Niccolò Machiavelli:

So, this is it: the book I absolutely don’t recommend for any reason. The Prince, in my opinion, has no business in, well, business. It’s all about the subterfuge of other ruling princes in Italy, and full of moral ambiguity as well as plenty of other issues. This book was commonly recommended for The Wolf of Wall Street types in the 1980s. You know, the guys in power suits who are brokering deals and gobbling up cocaine-like Charlie Sheen in Wall Street. It’s usually assholes that take advice from this book, so stay far, far away.

Becoming a leader should be your chance to use your power for AWESOME, not for evil, so be careful what you read. If you need a little help finding that awesome, please check out the 3 Books I DO Recommend for New Leaders, listen to my podcast, and contact me for some one-on-one coaching.


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