Top 10 Leadership Books

The Old Library @ Trinity College

Due to “popular” demand… I have created a shortlist of the top 10 leadership / management books which left a dent on my universe (ordered by year)

Note: There is no #11 in Top 10 shortlists so I had to keep some other amazing books out of this list … but I would love to learn what you think I am missing and made a dent on your universe?

So… The gist of it is:

• Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink and Leif Babin (2017)
• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz (2014)
• Start with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek (2009)
• Strengths Based Leadership: Great Leaders, Teams, and Why People Follow by Tom Rath (2008)
• The Toyota Way: 14 Management Principles from the World’s Greatest Manufacturer by Jeffrey Liker (2004)
• The Five Dysfunctions of a Team: A Leadership Fable by Patrick Lencioni (2002)
• Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins (2001)
• The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change by Stephen R. Covey (1989)
• Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company by Andy Grove (1988)
• Peopleware: Productive Projects and Teams by Tom DeMarco (1987)

… And now with a few more details:

Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink and Leif Babin (2017)

“The leader is truly and ultimately responsible for everything.” ~ Jocko Willink

Two U.S. Navy SEAL officers who led the most highly decorated special operations unit of the Iraq War demonstrate how to apply powerful leadership principles from the battlefield to business and life.

Part I: Winning the war within

• Extreme ownership
• No bad teams, only bad leaders
• Believe
• Check the ego

Part II: Laws of combat

• Cover and move
• Simple
• Prioritise and execute
• Decentralised command

Part III: Sustaining victory

• Plan
• Leading up and down the chain of command
• Decisiveness amid uncertainty
• Discipline equals freedom: The dichotomy of leadership.

Note: People who liked this book have tendency also to like the sequel — The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win (2018)

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz (2014)

Ben Horowitz offers practical wisdom for managing the toughest problems business school and most classic management books doesn’t cover (mostly based on ben’s blog)

“Every time I read a management or self-help book, I find myself saying, “That’s fine, but that wasn’t really the hard thing about the situation.” The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal. The hard thing isn’t hiring great people. The hard thing is when those “great people” develop a sense of entitlement and start demanding unreasonable things. The hard thing isn’t setting up an organizational chart. The hard thing is getting people to communicate within the organization that you just designed. The hard thing isn’t dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare.”

Note: People who liked this book have tendency also to buy Ben’s sequel — What You Do Is Who You Are: How to Create Your Business Culture (2019)

Start with Why: How Great Leaders Inspire Everyone to Take Action is a book by Simon Sinek (2009)

I assume everybody in the world already saw some version of the golden circle (a.k.a. why, how, what) and/or the ted talk … Start with why is a super simple yet very powerful influence model.

Few quotes

• “People don’t buy WHAT you do, they buy WHY you do it.”
• “There are only two ways to influence human behavior: you can manipulate it or you can inspire it.
• “Very few people or companies can clearly articulate WHY they do WHAT they do. By WHY I mean your purpose, cause or belief — WHY does your company exist? WHY do you get out of bed every morning? And WHY should anyone care?”
• “You don’t hire for skills, you hire for attitude. You can always teach skills.”
• “Leadership requires two things: a vision of the world that does not yet exist and the ability to communicate it.”

Note: People who liked this book have tendency also to like another Simon Sinek leadership book — Leaders Eat Last: Why Some Teams Pull Together and Others Don’t (2017)

Strengths Based Leadership: Great Leaders, Teams, and Why People Follow by Tom Rath (2008)

“A leader needs to know his strengths as a carpenter knows his tools, or as a physician knows the instruments at her disposal. What great leaders have in common is that each truly knows his or her strengths — and can call on the right strength at the right time. This explains why there is no definitive list of characteristics that describes all leaders.” ~ Donald O. Clifton, Ph.D (a.k.a. the father of strengths-based psychology and the grandfather of positive psychology)

The book explores the topic of leadership through the lens of strengths. In addition to discussing how different leaders can create success through the application of their own strengths; It also examined the specific emotional needs people have to experience with their leaders in order to feel engaged and connected to the organization and their day-to-day work. Through this research, the authors brought forth four key areas of focus: trust, compassion, stability and hope. When people feel those things, they feel more involved in their companies.

Note: People who liked this book have tendency also to like another Gallup book — First, Break All The Rules: What the World’s Greatest Managers Do Differently (2016)

The Toyota Way: 14 Management Principles from the World’s Greatest Manufacturer by Jeffrey Liker (2004)

The Toyota Way has been called “a system designed to provide the tools for people to continually improve their work”

… The two pillars of the Toyota way of doing things are Kaizen (the philosophy of continuous improvement) and respect and empowerment for people.

The 14 principles of The Toyota Way are organized in four sections:

• Long-Term Philosophy
• The Right Process Will Produce the Right Results
• Add Value to the Organization by Developing Your People
• Continuously Solving Root Problems Drives Organizational Learning

The two focal points of the principles are continuous improvement and respect for people. The principles for a continuous improvement include establishing a long-term vision, working on challenges, continual innovation, and going to the source of the issue or problem. The principles relating to respect for people include ways of building respect and teamwork.

The Five Dysfunctions of a Team: A Leadership Fable by Patrick Lencioni (2002)

Patrick Lencioni has coached and observed thousands of CEOs and Fortune 500 management teams. And in his work as the president of management consulting firm, The Table Group, he said he saw very clear patterns in the behavioral tendencies that constituted for the majority of team breakdowns. So clear, he wrote a 229-page book about it.

He suggests starting with these five questions about your team:

• Do your team members openly and readily disclose their opinions?
• Are your team meetings compelling and productive?
• Does your team come to decisions quickly and avoid getting bogged down by consensus?
• Do your team members confront one another about their shortcomings?
• Do your team members sacrifice their own interests for the good of the team?

If you’ve answered “yes” to all five, you must be one incredible manager — great job! If you have answered “no” to any of these questions, you likely have some work to do.

“Great teams do not hold back with one another. They are unafraid to air their dirty laundry. They admit their mistakes, their weaknesses, and their concerns without fear of reprisal.”

The 5 dysfunctions are (proposed solutions in the book):

• Absence of trust — Unwilling to be vulnerable within the group
• Fear of conflict — Seeking artificial harmony over constructive passionate debate
• Lack of commitment — Feigning buy-in for group decisions creates ambiguity throughout the organization
• Avoidance of accountability — Ducking the responsibility to call peers on counterproductive behavior which sets low standards
• Inattention to results — Focusing on personal success, status and ego before team success

Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins (2001)

Collins and his research team identified a set of elite companies that had made the transition from good to great — and sustained that performance for at least fifteen years.

Collins identified several key characteristics in companies that made the leap from good to great.

• Level 5 Leadership: Leaders who are humble, but driven to do what’s best for the company.
• First Who, Then What: Get the right people on the bus, then figure out where to go. Find the right people and try them out in different seats on the bus (different positions in the company).
• Confront the Brutal Facts: The Stockdale paradox — Confront the brutal truth of the situation, yet at the same time, never give up hope.
• Hedgehog Concept: Three overlapping circles: What lights your fire (“passion”)? What could you be best in the world at (“best at”)? What makes you money (“driving resource”)?
• Culture of Discipline: Rinsing the cottage cheese.
• Technology Accelerators: Using technology to accelerate growth, within the three circles of the hedgehog concept.
• The Flywheel: The additive effect of many small initiatives; they act on each other like compound interest.

Few quotes

• “Good is the enemy of great”
• “Great vision without great people is irrelevant.”
• “A company should limit its growth based on its ability to attract enough of the right people.”
• “Greatness is not a function of circumstance. Greatness, it turns out, is largely a matter of conscious choice.”

Note: People who liked this book have tendency also to really like the sequels

• Built to Last: Successful Habits of Visionary Companies (2004)
• How The Mighty Fall: And Why Some Companies Never Give In (2009)
• Great by Choice: Uncertainty, Chaos, and Luck — Why Some Thrive Despite Them All (2011)

p.s. Not all these “elite” companies survived the the next 20 years and therefore the sequels are also interesting

The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change by Stephen R. Covey (1989)

Covey presents an approach to being effective in attaining goals by aligning oneself to what he calls “true north” principles based on a character ethic that he presents as universal and timeless.

“The key is not to prioritize what’s on your schedule, but to schedule your priorities”

The 7 habits:

• Be proactive
• Begin with the end in mind
• First things first | Matrix of importance vs urgency
• Think win-win
• Seek first to understand, then to be understood | 1. Ethos 2. Pathos 3. Logos
• Synergize!
• Sharpen the Saw; Growth (Kaizen — Continuous Improvement)

… and with a followup book (2004) … The 8th habit

• Find your voice and inspire others to find theirs

Inflection Point

Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company by Andy Grove (1988)

In Only the Paranoid Survive, Grove reveals his strategy for measuring the nightmare moment every leader dreads — when massive change occurs and a company must, virtually overnight, adapt or fall by the wayside — in a new way. … This is literally the 90s version for #Covid19 crisis management.

Grove calls such a moment a Strategic Inflection Point, which can be set off by almost anything: mega-competition, a change in regulations, or a seemingly modest change in technology. When a Strategic Inflection Point hits, the ordinary rules of business go out the window. Yet, managed right, a Strategic Inflection Point can be an opportunity to win in the marketplace and emerge stronger than ever.

Few quotes

• “The strategic inflection point is the time to wake up and listen”
• “Business success contains the seeds of its own destruction.”
• “Strategic changes don’t just start at the top. It starts with your calendar”
• “Businesses fail either because they leave their customers or because their customers leave them!”
• “Altogether too often, people substitute opinions for facts and emotions for analysis.”
• “A strategic inflection point is a time in the life of business when its fundamentals are about to change. That change can mean an opportunity to rise to new heights. But it may just as likely signal the beginning of the end”

Peopleware Mindmap by Hannah

Peopleware: Productive Projects and Teams by Tom DeMarco (1987)

Peopleware: Productive Projects and Teams is a 1987 book on the social side of software development, specifically managing project teams… It is the first book I read as a junior software team leader that pointed out the People come first and not the software when building software… I think it is the first leadership book I read.

Few quotes

• “The purpose of a team is not goal attainment but goal alignment.”
• “The fundamental response to change is not logical, but emotional.”
• “The manager’s function is not to make people work, but to make it possible for people to work.”
• “in the best organizations, the short term is not the only thing that matters. What matters more is being best. And that’s a long-term concept.”
• “You may be able to kick people to make them active, but not to make them creative, inventive, and thoughtful.”
• “People under time pressure don’t work better — they just work faster.”

Note: This post was originally published on my personal blog