Best Management Books: 14-Day Challenge to Build a Successful Team

Want to become a better leader and build a high-performing team? This 14-day challenge walks you through the best management books, helping you master essential skills for leadership, decision-making, and delegation.

Day 1

Start With Why says that great companies, organizations, and leaders are those who first understand their 'Why' - their purpose, cause, or reason for existing.

Simon Sinek shows how leading companies like Apple inspire extraordinary loyalty with a strong focus on 'Why' they do what they do, not 'What' they sell, or 'How' they do things.

"People don't buy what you do; they buy why you do it. And what you do simply proves what you believe." —Simon Sinek
Day 2

The 7 Habits of Highly Effective People is about becoming more effective at reaching our goals and leading others.

Stephen Covey says his teachings are based on timeless principles like personal responsibility, empathetic listening, and treating others with fairness.

"Most people do not listen with the intent to understand; they listen with the intent to reply." —Stephen Covey

Why read it?

This book teaches 7 key principles that you can apply to almost any area of life, kind of like a Swiss Army knife for personal development.

Stephen Covey shifts focus from the surface-level pursuits of busyness and status to the character ethic - which says true success is about who we are, not just what we achieve.

After all, being busy isn't a personality trait, no matter how much we pretend it is on social media. 🤷‍♂️

Day 3

Crucial Conversations teaches you how to handle difficult conversations at work and home, especially when people have opposing opinions, strong feelings, and the outcome matters.

The book gives you tools and strategies to speak honestly yet respectfully, so you can communicate your thoughts and needs, while maintaining good relationships.

"People who are skilled at dialogue do their best to make it safe for everyone to add their meaning to the shared pool—even ideas that at first glance appear controversial, wrong, or at odds with their own beliefs." —Kerry Patterson

Why read it?

Crucial Conversations equips you with practical tools to handle challenging conversations gracefully and effectively.

Whether it's a tough talk with a colleague, a heart-to-heart with a loved one, or negotiating in high-stress situations, this book helps you stay composed and achieve the best possible outcomes.

It's a must-read for anyone looking to improve their communication skills and build stronger relationships.

Day 4

"How to Win Friends and Influence People" by Dale Carnegie is a classic self-help book that offers practical tips for better communication and relationships.

It teaches key principles for handling people, making friends, influencing others, and becoming a respected leader.

The book highlights the importance of empathy, respect, and appreciation.

"You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you." —Dale Carnegie

Why read it?

The book is filled with timeless wisdom on how to build meaningful relationships and influence people positively.

It's not just about making friends but also about becoming a better communicator and leader.

I found the real-life examples and practical tips incredibly useful in both my personal and professional life.

You should definitely read it to enhance your social skills and become more effective in your interactions.

Day 5

"Extreme Ownership" by Jocko Willink and Leif Babin is a book about leadership and discipline, based on the authors' experiences as U.S. Navy Seals.

The core concept is that a true leader must take full responsibility for both the successes and failures of their team or organization.

"On any team, in any organization, all responsibility for success and failure rests with the leader. The leader must own everything in his or her world. There is no one else to blame." —Jocko Willink
Day 6

Getting Things Done is a system to help us be more organized and productive.

It basically turned into a popular movement during the early 2000's.

David Allen says we can feel in control of our busy work lives, simply by learning to manage our daily tasks effectively.

"Your mind is for having ideas, not holding them." —David Allen
Day 7

Who Moved My Cheese? is a fable about dealing with life's never-ending change.

Spencer Johnson describes four small characters living in a maze.

One day, their cheese suddenly disappears.

They can either resist the change and suffer, or learn to embrace it and move onto something better.

"Life moves on and so should we." —Spencer Johnson MD
Day 8

"The Lean Startup" by Eric Ries is about how to build new startup businesses smarter, using lean and agile methods.

It emphasizes launching a Minimum Viable Product, gathering customer feedback with scientific tests, and pivoting based on insights.

This approach helps quickly develop valuable products that truly benefit customers.

"A startup is a human institution designed to create a new product or service under conditions of extreme uncertainty." —Eric Ries

Why read it?

If you're banging your head against the wall trying to make your startup work, "The Lean Startup" can give you a much-needed plan for success.

Eric Ries flips traditional business launch strategies upside down, arguing for a smarter, not harder, approach.

It's all about building a minimal product, getting it out there fast, "failing fast," and then tweaking it based on real feedback. (Rather than perfecting something in a vacuum and hoping it flies.) Think of it like playing a video game where you get a bunch of lives to keep trying. 🎮

Day 9

The Ride of a Lifetime is an inside look at leadership, from former Disney CEO Robert Iger.

You'll see how he earned so many promotions, managed people to avoid resentment, and negotiated billion-dollar deals.

"True authority and true leadership come from knowing who you are and not pretending to be anything else." —Robert Iger
Day 10

Getting to Yes is the most important book on negotiation, according to many professionals.

It comes from leaders of The Harvard Negotiation Project, who wanted to help people negotiate agreements with less time and friction.

The four steps of the method are: people, interests, options and criteria.

"If you want someone to listen and understand your reasoning, give your interests and reasoning first and your conclusions or proposals later." —Roger Fisher
Day 11

Traction explains an 'operating system' that can help entrepreneurs achieve more control and organization in your business.

Gino Wickman has assembled many practical management tools including: a 10-year vision, a people-grading chart, a data dashboard, a systems documentation method, and 90-day priorities called "Rocks."

"Above all else, your leaders need to be able to simplify, delegate, predict, systemize, and structure." —Gino Wickman

Why read it?

If you're burning out trying to push your small business beyond the startup phase and into real, sustainable growth, "Traction" by Gino Wickman may be right for you.

Wickman cuts through the noise with the Entrepreneurial Operating System (EOS), a clear framework that has helped many business owners stop spinning their wheels; and finally gain the grip to drive their business forward. 🛞

Day 12

Shoe Dog is an inspiring story of entrepreneurship from Nike's founder Phil Knight.

He started as a regular kid who loved running and built the largest sportswear brand ever.

But there were many challenging times that Nike barely survived.

"Let everyone else call your idea crazy... just keep going. Don't stop. Don't even think of stopping until you get there, and don't give much thought to where 'there' is. Whatever comes, just don't stop." —Phil Knight
Day 13

Influence is about six principles of persuasion useful for sales, marketing, and negotiation.

Professor Robert Cialdini backs his ideas with a lot of science research.

The six principles are: reciprocity, commitment and consistency, social proof, liking, authority and scarcity.

"Our best evidence of what people truly feel and believe comes less from their words than from their deeds." —Robert Cialdini

Why read it?

Influence may be the greatest marketing book of all time.

But more than that, like a secret playbook of the human mind—a deep dive into our decision-making process.

Think of it as a crash course in "Why did I just agree to that?" or "Why did I just buy that?" It's a must-read, whether you are a marketer, salesperson, or you just want to communicate with more influence.

By the end, you'll understand why we say "yes" to things that make no sense, from buying stocks we know nothing about to subscribing to that cheese-of-the-month club. 🧀

Day 14

Made in Japan is the autobiography of Akio Morita, who co-founded Sony and grew it to become one of the largest electronics companies in the world.

Akio shares his advice for management, leadership and innovation.

He also explains many differences in the working culture between Japan and the West.

"No matter how good or successful you are or how clever or crafty, your business and its future are in the hands of the people you hire. To put it a bit more dramatically, the fate of your business is actually in the hands of the youngest recruit on the staff." —Akio Morita
đź“š Bonus Books: These are extra recommendations to go beyond your challenge!
Day 15

Zero to One is about the future of technology and a guide for startup business founders.

Peter Thiel is a billionaire entrepreneur and investor that shares many unconventional ideas.

He says entrepreneurs should avoid competition.

Instead build a (legal) monopoly selling something completely new and incomparable.

"The perfect target market for a startup is a small group of particular people concentrated together and served by few or no competitors." —Peter Thiel

Why read it?

If you're trying to come up with an innovative new business idea, or if you're struggling to stay afloat in an overcrowded market, Peter Thiel's "Zero to One" may be your life jacket.

Peter Thiel, the entrepreneur and investor behind major names like PayPal, Facebook and Palantir — challenges us to think about creating something so unique it goes from zero (nonexistent) to one (the first of its kind).

This isn't about following trends; it's about setting them.

This book urges you to look where others don't and think differently. 🏆

Day 16

Sam Walton: Made in America shows how Walmart grew from one small store into the largest retail business in the world.

Sam Walton is often seen as one of the greatest entrepreneurs ever.

His journey was filled with risk, obstacles, adversity, failure... but also fun, discovery, passion and persistence.

"You've got to give folks responsibility, you've got to trust them, and then you've got to check on them." —Sam Walton
Day 17

The E-Myth Revisited by Michael E. Gerber is a crucial read for entrepreneurs, explaining why 80% of small businesses fail and offering invaluable strategies for success.

It teaches how to get your business to run without you, using systems and processes, that reduce your work and stress.

It shows how to work ON your business, not just IN it.

"That Fatal Assumption is: if you understand the technical work of a business, you understand a business that does that technical work." —Michael E. Gerber

Why read it?

Decades after it was published, this book continues to be a much-recommended bestseller for entrepreneurs worldwide.

Its evergreen popularity is proof of the timeless business wisdom packed inside.

If you’ve ever questioned why running your “dream business” feels more like working a nightmare 80-hour-per-week job, then this book is what you need!

It’s like having a business coach in your pocket, telling you exactly HOW to work smarter rather than harder. (Hint: by building systems in your business.)

Day 18

"Measure What Matters" by John Doerr is a book about a system called OKRs (Objectives and Key Results).

It’s a simple way to set goals and measure progress so you can stay focused and get things done.

The book shows how big companies like Google and Intel use OKRs to dominate their industries, and how you can use them too—whether for a team, a business, or even for your personal goals.

"A management methodology that helps to ensure that the company focuses efforts on the same important issues throughout the organization." —John Doerr

Why read it?

You should read Measure What Matters because it teaches a super simple and powerful way to set goals as a team and actually achieve them. There are great case studies from inside top companies and startups like YouTube, Adobe, and MyFitnessPal.

Trying the method, I was able to focus on my top goals and make progress on them in a measurable way.

If you want a clear plan for reaching your goals and a way to track how you're doing, this book is awesome.