9 Problem-Solving Books Every Entrepreneur Should Read

UPDATED: May 14, 2024
PUBLISHED: October 15, 2021
9 Problem-Solving Books Every Entrepreneur Must Read

You need problem-solving skills to succeed in work and in life. Whether you are an entrepreneur or an employee with an entrepreneurial approach, solid decision-making is paramount. We recommend each of these books to hone your problem-solving skills and level up in business and life. 

Cracked it!: How to Solve Big Problems and Sell Solutions Like Top Strategy Consultants

By Bernard Garrette, Corey Phelps, and Olivier Sibony

Poor decision-making leads to undesired outcomes. But what is the source of poor decisions in the first place? The flaw often resides in our own biases. For instance, we may think we understand a situation better than we do. Or we fall victim to confirmation bias. Cracked It! presents a four-step approach developed from the worlds of consultancy and cognitive psychology to achieve better outcomes. Avoid the pitfall and learn how to solve problems like a pro.

Think in Systems: The Art of Strategic Planning, Effective Problem Solving, And Lasting Results

By Zoe McKey

A systems approach to problem-solving can dramatically improve outcomes both in business and in your personal life. Best-selling author and lifestyle coach Zoe McKey shows you how to see beyond the individual parts of a problem you want to resolve. Rather, you will learn to take in the whole. And you will discover that every issue is but a piece of a larger system. McKey’s concise, enjoyable is a must-read for strategic problem-solving.

Solving the People Problem: Essential Skills You Need to Lead and Succeed in Today’s Workplace

By Brett M. Cooper and Evan Kerrigan

It sometimes seems your biggest problem can be other people. We all think and behave differently. That is the core strength of any team. But it can also lead to workplace conflicts. In Solving the People Problem, authors use the DiSC (Dominance, influence, Steadiness and Conscientiousness) model of self-awareness to help the reader develop emotional intelligence, or EQ. Build your EQ, and learn to solve “the people problem” for a stronger, more productive workplace. 

Creative Acts for Curious People: How to Think, Create, and Lead in Unconventional Ways (Stanford d.school Library)

By Sarah Stein Greenberg

As an executive director at Stanford, Sarah Stein leads designers, faculty, and other innovative thinkers to discover and apply their creative abilities. In Creative Acts for Curious People, she guides you to build your own creative skills with a fun, often light-hearted approach. But make no mistake: her enjoyable exercises are fully based in research and practice. Boost your creativity and learn to solve complex problems in new ways with Creative Acts for Curious People.

The Collaborative Path: 6 Steps for Better Communication, Problem-Solving, and Decision-Making

By Patrick Aylward

We rarely solve problems in isolation. We typically solve problems and make decisions collaboratively. And successful collaboration depends mostly on quality communication. Author Aylward lays out a six step approach for better decision-making as a team. Learn to de-escalate conflicts and reduce tensions for stronger, more successful team decision-making.

You’re About to Make a Terrible Mistake: How Biases Distort Decision-Making and What You Can Do to Fight Them

By Olivier Sibony

One thing often holds us back from making a decision: we are afraid we will make the problem worse. It doesn’t matter how smart you are. We all make mistakes. These can be errors based on bias, or simply poor judgment. In You’re About to Make a Terrible Mistake, professor and strategic thinking advisor Olivier Sibony investigates nine common decision-making traps. More importantly, he provides ample methods on how to best avoid them. Filled with great examples and plenty of humor, this book serves as a great tool toward overcoming our biases and making better decisions.

Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts

By Annie Duke

We rarely have all the information required to make the best possible decision. This uncertainty can lead to self-doubt and analysis paralysis: failure to move forward as we over-analyze. Amazon best-selling author Annie Duke shows you how to make decisions by approaching them as bets. Is there ever a 100% chance that your decision will result in exactly the outcome you imagined? Rarely. But if there’s a 90% chance of reaching 80% of your goal… that’s a good bet.

Think Smarter: Critical Thinking to Improve Problem-Solving and Decision-Making Skills

By Michael Kallet

An older book on the list, Think Smarter stands out as much today as it did in 2014. Founder of Headscratchers, author Michael Kallet has helped business leaders solve problems for more than 30 years. In this book, he provides 25 tools to help you ask the right questions, avoid errors, and think more critically in any dilemma. Ample exercises train your brain to reach solutions and solve problems with innovation and clarity.

Bulletproof Problem Solving: The One Skill That Changes Everything

By Charles Conn and Robert McLean

Are you ready for logic trees? Those of you who have used them for problem-solving may have just cringed. That’s because many of us have used them without knowing how. In Bulletproof Problem Solving, authors Conn and McLean provide clarity through a simple, seven step method. Learn more effective brainstorming practices and how to overcome biases. Plus, they’ll show you how to turn your outcomes into a great story. With 30 detailed case studies, you’ll learn how to effectively solve problems from the micro all the way to global leadership.

Photo by @Asheesh/Twenty20

Bryan Lindenberger

Bryan enjoys the digital space where arts and technology meet. As a writer, he has worked in education, health and wellbeing, and manufacturing. He also assists smaller businesses in web development including accessibility and content development. In his free time, he hikes trails in central Florida.