Best Leadership Books

Best leadership books

This is a selection of the best leadership books that I personally have read.

Albeit it’s called “best leadership books“, it’s actually a “best leadership resources” list, since it considers any source of knowledge such as video, courses, or podcasts.

Let’s start:

13. Lean In

lean in

Summary | Audiobook

I wholeheartedly disagreed with most of Sheryl Sandberg’s opinions.

Not just because she doesn’t take into account basic human psychology, but also because her recommendations are divisive and running contrary to the positive humanistic ideals that I hold dear (see “Enlightenment Now” by Steven Pinker).

Yet, that being said, Lean In contains great wisdom for women in business.
Just one example: women should negotiate from a “we” position because assertive women are disliked across the board.
The driven female readers might not like that, but it’s true and it’s the type of information that will only make it more likely that women will advance to the position they deserve.

If you’re a woman reading here, you will learn that same content, plus more, from this shorter post:

Leadership QuoteDone is better than perfect


12. How To Win Friends And Influence People

how to win friends and influence people

Summary | Audiobook

How to Win Friends and Influence people is not strictly a leadership book per se.
But it can help many current and future leaders understand that top-down “orders” often breed resentment and have little buy-in.

This is not to say that strong top-down leadership has no place: there are times and situations when it’s the way to go -or the only way to go-. But as a rule of thumb, authoritarian leadership is not good for long term performance -and, often, for the survival of the leader himself-.

Also read: saving face and never outshining the master.

Leadership quoteAny fool can criticize, complain, and condemn—and most fools do. But it takes character and self-control to be understanding


11. Extreme Ownership

extreme ownership

Summary | Audiobook

I’m not a huge fan of military guys coming out of war deployment and writing books.

It feels like they’re selling hype to the civilian population who wants to buy some “danger” and “excitement” through vicarious living.
And of course, that’s not even to mention the often unneeded destruction, pain, and murder they bring about -without making this political, but who took ownership of finding those weapons of mass destruction?-.

Anyway, back to us, Extreme Ownership has some much-needed mindsets that leaders the whole would over should really, well… Own :).
The title of the book itself is probably the main takeaway: leaders must take responsibility for everything which happens in their team.

Leadership QuoteThere are no bad teams. Only bad leaders.


10. The Leadership Challenge

the leadership challenge book cover

Summary | Amazon

This is the best “manual” type of leadership book that I have ever seen. For any aspiring leaders, I would probably recommend starting with The Leadership Challenge.

Leadership QuoteExemplary leaders know that if they want to gain commitment and achieve the highest standards, they must be models of the behavior they expect of others 


9. Leaders Eat Last

Leaders eat last

Summary | Amazon

Leaders Eat Last is one of the best leadership books because if all leaders heeded Simon Sinek’s message we would live in a much better world.

Sinek says that leaders, by virtue of their positions, enjoy a plethora of advantages.
However, great leaders also need to shoulder the responsibilities of leadership, which include leading by example, eating last when food is scarce and taking care of the people by shouldering the risks and downsides.

I don’t fully agree with Sinek’s assertion that leaders are not responsible for final results and I disagree with some of the “softer” approaches. In life, there also happen situations when an iron first is more needed.

That being said, leaders Eat Last is a wonderful book and must-read for anyone who aspires to be the best possible leader they can be.

Leadership Quote: You can easily judge the character of a man by how he treats those who can do nothing for him


8. Eleven Rings

eleven rings

Summary | Amazon

If you are planning to lead top-performing teams, then you might learn a thing or two from the guy who has coached some of the most talented, motivated, and driven men in the history of basketball (including Michael Jordan, Pippen, Kobe Bryant).

It’s particularly interesting because some of the top athletes he coached didn’t like each other and were quarreling for the leader’s position in the team (Shaquille O’Neal VS Kobe Bryant) while some others were pure rebels by nature (Dennis Rodman).

Lots to learn on leadership here when it comes to super-driven individuals working together.

Leadership Quote: the secret of managing is to keep the guys who hate you away from the guys who are undecided.


7. The 21 Irrefutable Laws Of Leadership

21 irrefutable laws is one of the best leadership books

Summary | Amazon

My absolute favorite lesson is the Law N.1, which Maxwell calls “The Law of The Lid”.
It states that the effectiveness of the leaders is the maximum threshold to which the team can operate.
I personally apply an even wider meaning to this rule. To me it mans that any leader must be in some form or respect “superior” to the team in some important and recognized trait.
That could be decisiveness, strength, wisdom, experience or strength of values and beliefs (charismatic leadership).

I have indeed seen plenty of managers who could NOT keep good people in their teams because they were, simply, inferior individuals in core aspects of their personalities -including, crucially, in ethics and morals-.

In a nuthsell, to be a great leader, be a great man (or great woman).

Leadership Quote: leadership isn’t how far we advance ourselves but how far we advance others


6. Drive

drive

Summary | Amazon

Drive can fix some of the most glaring deficiencies of managers’ understanding when it comes to human nature.

All the information on human psychology and what motivates people is out there.
It doesn’t require managers, leaders or anyone else to reinvent the wheel. It requires some basic reading and not going through our lives with our eyes shut (figuratively).

“Drive” is one of the best leadership books because it provides one of the most important pieces to understand human nature when it comes to work, team performance, and motivation.
And it’s this: extrinsic motivators such as salary and material rewards don’t produce passion and motivation. On the contrary, they can crow out intrinsic motivation.
To learn more about the phenomenon also read The Social Animal by Elliot Aronson.

Leadership Quote: control leads to compliance; autonomy leads to engagement


5. Delivering Happiness

delivering happiness

Summary | Amazon

Leadership has been linked to decisiveness, to strength and courage, and also to empathy and vulnerability.

But to happiness? Not so often!

And that’s why “Delivering Happiness” cracks the TOP 3 of best leadership books. Not only Tony Sieh made happiness a key value of Zappos, but he also tried to track it on his way to a multi-million dollar exit.

Turns out, as The Happiness Advantage explains, happiness actually precedes success, and not the other way around.

Leadership Quote: money alone isn’t enough to bring happiness.. Happiness is when you’re actually truly ok with losing everything you have.


4. Principles

Summary | Amazon

If you want to develop a culture that is all about growth, learning and, ultimately, top performance, then Principles by Ray Dalio is simply the best organizational book available.

It’s not easy to implement because the key principles of radical open-mindedness and radical transparency requires a buy-in into meritocracy that goes beyond ego and personal fiefdoms of power.
In many ways, they go against the “default” human nature that most of us are born with.

Yet, by developing an antifragile ego and a growth mindset, we can all tap into what’s our next stage of human wisdom and power.
And maybe, on the way there, build a multi-billion company as Ray Dalio did :).

Leadership Quote: truth – more precisely, an accurate understanding of reality – is the essential foundation for producing good outcomes.


3. Underboss

underboss book cover

By Peter Maas
Summary

What’s so good about this book?

That while all the others before talk about leadership, Underboss shows you leadership.

Especially, you will learn from the failures of leadership, and the Machiavellian aspects of leadership.
And that makes it one of the best on this list, much more “real life” than bla bla bla on what makes a great leader.

Leadership Quote: “It was a big disgrace for the family. A real black eye. You give him up in five minutes to the Genovese family? Would you want your father giving you up like that? That was a bad, bad move Paul made. A real bad move. You want to know your boss is going to fight for you tooth and nail

2. Radical Candor

radical candor book cover

By Kim Scott
Summary | Audiobook

If you’re looking for leadership books that can help you in your business or in your team at work, look no further.

Kim Scott’s approach is designed to develop top-performing teams via both radically honest feedback and personal caring towards the people.

It’s best suited for best-performing companies and teams. You probably cannot use the wisdom of this book if you’re in a company where office politics is the name of the day and if you’re not yet a high-level manager.
For that, read “best career strategies books“.

But if you want to create the best possible working environment, where people can grow the most and where you work is performed in the most effective way possible, look no further.

Leadership quote: I once worked for a man who told me, “In every relationship there is a screwer and a screwee.” Needless to say, I didn’t work for him for long.


1. The New Psychology Of Leadership

the new psychology of leadership

By Alexander Haslam
Summary | Amazon

The true ground zero of all leadership books. 

It makes all other leadership books pale in comparison. 

Yes, it’s heavy.
Yes, it’s long.
Yes, it’s full of academic research.
And yes, it’s even expensive.

And no, if you’re looking for the entertaining book with a war story look somewhere else.
This one is not about entertainment.

But if you’re looking for leadership wisdom, then here you can from actual research.

And if you’re looking for the best leadership books, then you can stop looking.
This is it.

Leadership Quote: Leadership that is grounded in shared identity will always win out over that which is grounded in ego.


Great Leadership Books

Outside of the TOP 10, but still with plenty of wisdom:

My expectations for leadership a book with the title “One Minute Manager” were not sky high as I expected some sort of “managing for dummies” kind of content.

Instead, it was simple and powerful, short and to the point.
Any boss applying these principles in their managerial activities are sure to improve their teams’ morale and performance.

Onward embodies the spirit of the man who is driven by his passion and deeply in love with his craft.
At times, it feels almost like a (positive) fetish.
The first time Howard Schultz walked into an Italian bar he thought it was live comedy, and became obsessed with replicating the same experience worldwide.
Starbucks was born (which this Italian doesn’t really like too much, BTW :).
Onward is also an awesome book to understand the spirit of a man who considers his company his family -albeit I think employees shouldn’t fall for that: your company is never your family-.

While not technically a leadership book, it’s super helpful for everyone working in any artistic endeavors. Steven Pressfield says that artists also need systems, hard work, and a good dose of realism.
As Steve Jobs said “real artists ship”.

In Ben Horowitz work I especially liked the psychology behind the “enemies within”, such as the disgruntled employees who do work little and secretly undermine the team’s efforts.
That’s something that few other leadership books talk about (Robert Greene and this website being two exceptions).

For people seeking the leadership of for-profit organizations Good to Great shows both what distinguishes great companies from average ones (a relentless focus on quality and sustainable growth) and what distinguishes great leadership from average one (share credit and takes blame; modest; want to see the company success even after they’re gone)

One of the best leadership books to understand the importance of teamwork, trust among team members, and how the free flow of opinions and information differentiates top-performing teams from average ones.

Possibly the best leadership book when it comes to creative organizations and creative cultures.
The biggest takeaway for me: share the problems and the reasoning behind your choices. People will take ownership and will not waste time second-guessing what’s happening.

If you want to model a hard-driving, results first and people second type of leader, then Jack Welch is your man.
Warren Buffet said it’s the only book you’ll ever need to read on management. I don’t necessarily agree, but it’s definitely a significant endorsement -and I also actually loved the book-.

Kouzes and Posner, the same authors as “The Leadership Challenge”, are two big names in the leadership literature. And for good reasons: they write simply and without frills while going at the core of what it means to be a great leader.
In this wonderful book, they boil it down to ten simple rules, all backed by research.

The biggest takeaway from “Primal Leadership” is that the different styles of leadership and the knowledge that you must master more than once to be a great leader.

Leadership has no extremes: it’s about walking the line.
A few great takeaways from this book, including that great leadership also means knowing when to follow, when to ask for more junior members’ opinions, and establishing a good relationship with your boss even if you don’t agree with him (or like him).

The main takeaway from this great book for me was that love is the core of leadership.
But since the ultimate role of the leader is to accomplish the mission, love also means that leadership is about making the tough decisions that can hurt the one for the good of the whole (something Ray Dalio also says in Principles).

Further Reading

Great Leadership Is Experience And Knowledge

If you are reading here you probably are a smart guy and you don’t need me to tell you but leadership, being intrinsically a people’s skill, is difficult to learn in written form.

It will certainly require experience and some mistakes by doing.
But don’t make the mistake of falling on the other side of the “wrong” spectrum: experience alone might not be enough. There are plenty of “leaders” with decades of experience who are still crappy leaders who demotivate their teams instead of leading them higher.

If you want to dig deeper on a source with deep psychology, videos, and quizzes to help you increase emotional intelligence and read social dynamics, check out Power University

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