Best Management Books for Common Leadership Challenges: The 2021 Edition

If you Google “best management books,” you’ll get thousands of results that may or may not address your particular leadership challenge. To help you out, we’ve done the research for you and categorized 15 of the best management books by common challenges that managers face. Take a look at our top picks to help you navigate everything from workplace culture to improving motivation.

Best Management Books for New Managers

If you’re a first-time manager, you’re likely inheriting an entirely new team, or your peers are becoming your subordinates. Either way, you’re in uncharted waters and need to learn fast how to give feedback, have tough conversations, and engage your team. These are three of the best management books to help if you’re just starting your management career.

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1. The Making of a Manager: What to do When Everyone Looks to You by Julie Zhuo

Whether you’ve been thrust into management or you’re battling impostor syndrome as people look to you for guidance, this book can help. Zhuo shares her own experience — the surge of excitement when being asked to lead a team, followed by the crushing realization that she was in completely unfamiliar territory. She doesn’t shy away from the awkward moments, and she stresses that “good managers are made, not born.” If you’re looking for a funny, relatable, and helpful guide to management, this book is for you.

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2. Radical Candor BY Kim Scott

The book that launched a thousand articles. What started as a guide for having challenging conversations with employees has morphed into a well-known management tactic that leaders continue to write and talk about, years after the book’s release.

In Radical Candor, Scott tackles one of the biggest challenges new managers face: giving feedback. Scott points out that managers often skew to one side — overly aggressive or overly empathetic. She provides a framework for striking a balance and approaching conversations with a sense of humanity while still inspiring employees to do their best work.

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3. Leadership Lessons from a UPS Driver: Delivering a Culture of We, Not Me BY Ron Wallace

Ron Wallace went from being a UPS driver to president of UPS International, overseeing over 60,000 employees. As the title suggests, his book encourages managers to promote teamwork over individual performance. Wallace says that working at UPS gave him a “PhD in teamwork,” and, in the book, he shares many stories that focus on the people he worked with during his journey. He stresses the importance of investing in your people by giving them the training and support they need to grow and then explains how you can do that in your organization.

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Sign up for a free coaching consultation with Uptick Co-founder Chris Zaugg to improve your team’s effectiveness by connecting relationally.

Best Management Books About Resolving Conflict and Other Sticky Situations at Work

As a leader, it’s your responsibility to resolve issues and set an example for how team members should handle conflict in the workplace. These are four of the best management books to help you work through difficult situations and tricky conversations.

4. The Hard Thing About Hard Things by Ben Horowitz

While many management books tell you how to do things correctly, this book is built on the assumption that mistakes and difficult situations are inevitable. In his book, Horowitz gets real about the struggles of laying people off, managing bad employees, and making tough business decisions.

“Hard things are hard because there are no easy answers or recipes,” Horowitz says. “They are hard because your emotions are at odds with your logic. They are hard because you don’t know the answer and you cannot ask for help without showing weakness.”

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5. Mean People Suck: How Empathy Leads to Bigger Profits and a Better Life by Michael Brenner

In his book, Brenner points out that many managers think they have to be mean in order to lead effectively. But he points to research and his personal experiences to show that compassion and empathy are much more effective management skills. He provides a helpful guide for how managers can embrace empathy to create happier, more successful businesses.

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6. No Hard Feelings: The Secret Power of Embracing Emotions at Work by Liz Fosslien and Mollie West Duffy

No Hard Feelings is the comic book/management guide crossover you didn’t know you needed. In this illustrated guide, Fosslien and West Duffy use funny, relatable comics to show you the value of letting yourself feel feelings at work.

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Fosslien and West Duffy share work-related comics on their Instagram page.

No Hard Feelings discusses the negative effects of suppressing your emotions at work and provides practical guidance for how you can be your authentic self while still keeping things professional.

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7. Crucial Conversations: Tools for Talking When Stakes Are High by Joseph Grenny, Ron McMillan, Kerry patterson, and Al Switzler

Crucial Conversations looks beyond the workplace and focuses on improving communication in every relationship. The authors, who are also cofounders of VitalSmarts, provide guidance on how to manage anger and hurt feelings, create safe spaces for every conversation, and how to be persuasive without being abrasive. Crucial Conversationspoints out that “each of us enters conversations with our own opinions, feelings, theories, and experiences about the topic at hand” and then shows the reader how they can prepare for high-stakes conversations.

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Best Management Books About Building a People-First Culture at Work

Culture is one of the things we tend to put second when it comes to leadership. We prioritize performance above most things (hitting KPIs), but many studies have shown that when you put culture first, performance improves. Building an inclusive culture where team members feel safe to voice their feedback and ideas without repercussion is key. These management books show you how to create a people-first culture at your company.

8. Leaders Eat Last by Simon Sinek

Simon Sinek has written multiple books on leadership, including the best-seller Start with Why, but this particular book focuses on the military philosophy of “Officers eat last,” which means high-ranking officers put themselves behind everyone else. Sinek shares examples from a variety of companies that show how putting your employees first and treating them well leads to a more positive work culture.

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9. Diversity in the workplace by Bärí A. Williams

Bärí A. Williams is an attorney, tech executive, diversity activist, public speaker, and writer. Her book, Diversity in the Workplace, is a collection of 25 interviews with different leaders, primarily in the tech space, on their experiences fighting inequality in the workplace. It’s an eye-opening and often shocking illumination of how race, gender, identity, age, ability, and religion affect work environments and people.

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10. It Doesn’t Have to be Crazy at Work by Jason Fried and David Heinemeier Hansson

In this book, Basecamp executives Fried and Heinemeier Hansson reject the idea that packed schedules and 80-hour workweeks are the keys to success. Instead, they embrace a feeling of calm in the workplace. It Doesn’t Have to be Crazy at Work shows how protecting people’s time and rejecting the endless hustle leads to more productive, successful businesses.

“Our benefits are focused on getting people out of the office, not enticing them to stay longer. … No ‘stay here’ signals. Everything’s about wrapping up your reasonable day, going home, and living your life.” – Basecamp

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Best Management Books for Motivating Your Team (and Yourself)

Regardless of your role, sometimes you just feel stuck. Blah. Flat. And, chances are, your team members experience burnout as well. Turn to these management books to identify your source of decreased motivation and learn how to reignite the spark.

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11. Year of yes by Shonda Rhimes

You probably know Shonda Rhimes as the creator of hit TV shows like Scandal and Grey’s Anatomy, but you might not have come across her award-winning book on, literally, a year of saying yes to everything. Post fame and success, Rhimes found it difficult being an introvert in a highly extroverted field and suffered from panic attacks and anxiety. After a comment from her sister over a Thanksgiving dinner, she decided to spend a year saying yes to everything, even the things that scared her the most. Her journey through fear and exploration is guaranteed to kick-start your motivation.

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12. The Power of Habit: Why We Do What We Do in Life and Business by Charles Duhigg

Ever wonder why it’s so hard to start that morning exercise routine or commit to taking regular lunch breaks? The Power of Habit looks at scientific discoveries and discusses why habits exist, how they form, and how we can change them. Duhigg provides a framework for identifying your routines and making plans to change your habits in a positive way.

“Change might not be fast and it isn’t always easy,” Duhigg says. “But with time and effort, almost any habit can be reshaped.”

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13. Give and Take by Adam Grant

Researcher, professor, and organizational psychologist, Adam Grant, dives into the not-so-common motivators for success in the workplace. Spoiler alerts ahead. Grant introduces the idea that there are three types of people in the workplace: givers, matchers, and takers. Through examples, analyses, and studies, he shows why and how givers are often those who rise to the top of the performance ladder.

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Bonus Reads

These books don’t tie back to a specific leadership challenge. However, they contain valuable advice from people who built impressive companies and cultures, so the books are worth adding to your list.

14. The Power of Wow: How to Electrify Your Work and Life by Putting Service First by The Employees of Zappos

The fact that the byline went to “the employees of Zappos” should already tell you a bit about the company culture at Zappos. While Zappos makes its money from selling shoes and accessories, the company hopes that people will think of Zappos as “a service company that just happens to sell ________.”

The Power of Wow is a collection of stories from employees that shows how keeping customers and employees happy has made Zappos such a resilient business.

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15. Trailblazer by Marc Benioff

From the founder and CEO of Salesforce comes an insightful read about building a company culture around your values. “Lots of businesses talk about values, but in turbulent times, when they matter most, executives often forget to operationalize them” Benioff says.

In this book, Benioff shares best practices for leaders who want to inspire employees to do their best work and set the company up to thrive during challenging times.

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Great Leaders Are Always Learning

We hope some of these books make it onto your to-read list! If you’d like to supplement your reading, be sure to check out 13 Leadership Videos to Help You Craft Your Leadership Style and The 16 Best Management Podcasts of 2020.

Want to be a better manager with a happier, healthier and more effective team? 

Sign up for a free coaching consultation with Uptick Co-founder Chris Zaugg to improve your team’s effectiveness by connecting relationally.

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