Here are 100 books that Playing to Win fans have personally recommended if you like Playing to Win. Shepherd is a community of 12,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Difficult Conversations: How to Discuss What Matters Most

Tyra P. Sellers Author Of Daily Ethics

From my list on books to help you master tricky conversations with kindness.

Why am I passionate about this?

I’ve spent a lot of my career teaching people to navigate the complex, often messy intersection of ethics, communication, and human behavior. As a behavior analyst, teacher, supervisor, and coauthor of Daily Ethics: Creating Intentional Practice for Behavior Analysts, I’ve seen firsthand how the ability to have honest, compassionate, and courageous conversations can make or break relationships, teams, and outcomes. I chose these five books because they’ve shaped how I show up in my work and life—and because I have seen their contents help others become more intentional, committed, and successful communicators.

Tyra's book list on books to help you master tricky conversations with kindness

Tyra P. Sellers Why Tyra loves this book

I recommend this book because it taught me that every hard conversation has three layers: what happened, what’s felt, and what that means to each person.

Before reading it, I often got stuck on the “facts” and missed the emotional undercurrent, especially for my communication partner.

Now, I approach challenging discussions with a mental checklist from Difficult Conversations that helps me listen for what’s beneath the words. It has saved me from countless misunderstandings and made me a much better listener and collaborator.

By Douglas Stone , Bruce Patton , Sheila Heen

Why should I read it?

8 authors picked Difficult Conversations as one of their favorite books, and they share why you should read it.

What is this book about?

The 10th-anniversary edition of the New York Times business bestseller-now updated with "Answers to Ten Questions People Ask"

We attempt or avoid difficult conversations every day-whether dealing with an underperforming employee, disagreeing with a spouse, or negotiating with a client. From the Harvard Negotiation Project, the organization that brought you Getting to Yes, Difficult Conversations provides a step-by-step approach to having those tough conversations with less stress and more success. you'll learn how to:

· Decipher the underlying structure of every difficult conversation 
· Start a conversation without defensiveness 
· Listen for the meaning of what is not said 
·…


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Book cover of The High House

The High House by James Stoddard,

The Victorian mansion, Evenmere, is the mechanism that runs the universe.

The lamps must be lit, or the stars die. The clocks must be wound, or Time ceases. The Balance between Order and Chaos must be preserved, or Existence crumbles.

Appointed the Steward of Evenmere, Carter Anderson must learn the…

Book cover of Thinking, Fast and Slow

Ryan Christensen Author Of Winner Peace

From my list on succeed in life from a hypnotist.

Why am I passionate about this?

I’ve spent my entire life dealing with mental health issues, and overcoming them took me on a long journey of learning about the mind and how to make it work for us rather than against us. I’ve explored almost every modality out there and developed my own hypnosis modality as a result. Books like these were a key part of helping me figure out how to overcome my challenges and live life to the fullest, achieve my goals, and reach success.

Ryan's book list on succeed in life from a hypnotist

Ryan Christensen Why Ryan loves this book

It wasn’t until reading this book that I realized how important it was to focus on the fast, instinctive part of our mind. Getting that initial judgment and reaction right makes everything else easier. Too often, I found myself wanting to understand things logically and rationally, assuming that my instincts and emotions were simply wrong.

This book helped me understand how useful both systems were and how to leverage them to achieve my goals faster and more effectively.

By Daniel Kahneman ,

Why should I read it?

48 authors picked Thinking, Fast and Slow as one of their favorite books, and they share why you should read it.

What is this book about?

The phenomenal international bestseller - 2 million copies sold - that will change the way you make decisions

'A lifetime's worth of wisdom' Steven D. Levitt, co-author of Freakonomics
'There have been many good books on human rationality and irrationality, but only one masterpiece. That masterpiece is Thinking, Fast and Slow' Financial Times

Why is there more chance we'll believe something if it's in a bold type face? Why are judges more likely to deny parole before lunch? Why do we assume a good-looking person will be more competent? The answer lies in the two ways we make choices: fast,…


Book cover of Mindset: The New Psychology of Success

Alan Gregerman Author Of The Wisdom of Ignorance

From my list on unlocking your curiosity and awesomeness.

Why am I passionate about this?

I am, first and foremost, someone who cares deeply about the world, people, and learning. I have been passionate about ideas, curiosity, and innovation since I was a child and since starting our company and writing four books, have had the privilege of helping over 400 organizations and 700,000 people to unlock their genius by not being experts but by being curious about the world around them and other people. I am also a teacher, speaker, and community volunteer who is keen to help people find their own unique brilliance.

Alan's book list on unlocking your curiosity and awesomeness

Alan Gregerman Why Alan loves this book

I love this book because it is all about how we show up each day and how we engage the world.

I am particularly keen on the idea that we can choose to be open to learning new things, meeting new people, and making a difference…in other words, we can choose to “grow” …or we can choose to stand still.

And I hope that I will never stop wanting to know more, read more, learn, and try to make a difference.

By Carol S. Dweck ,

Why should I read it?

19 authors picked Mindset as one of their favorite books, and they share why you should read it.

What is this book about?

From the renowned psychologist who introduced the world to “growth mindset” comes this updated edition of the million-copy bestseller—featuring transformative insights into redefining success, building lifelong resilience, and supercharging self-improvement.

“Through clever research studies and engaging writing, Dweck illuminates how our beliefs about our capabilities exert tremendous influence on how we learn and which paths we take in life.”—Bill Gates, GatesNotes

“It’s not always the people who start out the smartest who end up the smartest.”

After decades of research, world-renowned Stanford University psychologist Carol S. Dweck, Ph.D., discovered a simple but groundbreaking idea: the power of mindset. In this…


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Book cover of December on 5C4

December on 5C4 by Adam Strassberg,

Magical realism meets the magic of Christmas in this mix of Jewish, New Testament, and Santa stories–all reenacted in an urban psychiatric hospital!

On locked ward 5C4, Josh, a patient with many similarities to Jesus, is hospitalized concurrently with Nick, a patient with many similarities to Santa. The two argue…

Book cover of Confessions of an Advertising Man

Mark Beal Author Of ZEO: Introducing Gen Z – The New Generation Of Leaders

From my list on inspiring creativity, transformation, and innovation.

Why am I passionate about this?

For more than 30 years I have been immersed in creative public relations and marketing from campaign development and activation to effectively engaging the primary consumer audiences. Me and my teams developed campaigns around such major sports and entertainment properties as the Olympic Games, Super Bowl, and The Rolling Stones. No matter your industry, inspiration for creativity, transformation, and innovation can come from many sources including the compelling storytelling featured in the books that I recommend.  

Mark's book list on inspiring creativity, transformation, and innovation

Mark Beal Why Mark loves this book

Often called the “Father of Advertising,” David Ogilvy pulls back the curtain on his career and the advertising industry in the mid to late 1900s.

Strategic and creative approaches to marketing that he and his colleagues took decades ago are still timely, relevant, and applicable in today’s social and digital media world.  

By David Ogilvy ,

Why should I read it?

4 authors picked Confessions of an Advertising Man as one of their favorite books, and they share why you should read it.

What is this book about?



A new edition of the timeless business classic featured on Mad Men—as fresh and relevant now as the day it was written

 

"We admire people who work hard, who are objective and thorough. We detest office politicians, toadies, bullies, and pompous asses. We abhor ruthlessness. The way up our ladder is open to everybody. In promoting people to top jobs, we are influenced as much by their character as anything else."  —David Ogilvy

 

David Ogilvy was considered the "father of advertising" and a creative genius by many of the biggest global brands. First published in 1963, this seminal book revolutionized…


Book cover of The Tipping Point: How Little Things Can Make a Big Difference

Denise Brinkmeyer Author Of Project Orienteering: A Field Guide For Project Leadership

From my list on servant leaders who get things done.

Why am I passionate about this?

I am the oldest child, and former teacher turned technology innovator. As the only girl, growing up with three brothers gave me the tenacity to overcome limiting beliefs. Information technology has helped me create an environment where I can help a lot of people. At the end of the day, what I love most is helping someone turn an idea into a tangible solution while motivating team members to see the beauty and joy in this type of service.  

Denise's book list on servant leaders who get things done

Denise Brinkmeyer Why Denise loves this book

Malcolm Gladwell never disappoints me. He has said that when people meet him, they treat him like they know him. After years of reading his books and listening to his podcasts, his voice sounds like a friend's.

This book is one of my favorites because it gives me hope that with the right ingredients of passion, hard work, and opportunity, our efforts will tip toward success. It reminds me to open my eyes and watch for opportunities so that when we are in the business of passionate service, we may end up on a great adventure that we could not have predicted.

By Malcolm Gladwell ,

Why should I read it?

7 authors picked The Tipping Point as one of their favorite books, and they share why you should read it.

What is this book about?

An introduction to the Tipping Point theory explains how minor changes in ideas and products can increase their popularity and how small adjustments in an individual's immediate environment can alter group behavior.


Book cover of The Attention Merchants: The Epic Scramble to Get Inside Our Heads

Carol M. Glen Author Of Controlling Cyberspace: The Politics of Internet Governance and Regulation

From my list on understanding the internet and how it is governed.

Why am I passionate about this?

I’m a professor of political science at Valdosta State University in Georgia, USA. I have long had an interest in new technology and its implications for international relations and society. I have taught classes on international relations, global public policy, and international institutions. I have also published in these areas. Since the internet has been a disruptive force in both the national and international environments, I believe, as a political scientist, that it is vital to understand its effects on existing power relationships. I hope you find the books on my list enlightening.    

Carol's book list on understanding the internet and how it is governed

Carol M. Glen Why Carol loves this book

In today’s media environment of 24-hour news, clickbait, and social media, there is tremendous competition to grab our attention. Our attention and our data have become commodities that can be monetized and sold to the highest bidder.

I love this book because Wu places this struggle for our attention in a broader historical context, tracing its roots to a 19th-century newspaper owner who discovered that advertising revenue could bring in more profits than the price he charged for newspapers. This business model has been applied to radio, television, and now the internet, but the goals remain the same.

Wu is a consummate storyteller and provides numerous examples of how we are being manipulated for profit. 

By Tim Wu ,

Why should I read it?

8 authors picked The Attention Merchants as one of their favorite books, and they share why you should read it.

What is this book about?

Attention merchant: an industrial-scale harvester of human attention. A firm whose business model is the mass capture of attention for resale to advertisers.
In nearly every moment of our waking lives, we face a barrage of advertising enticements, branding efforts, sponsored social media, commercials and other efforts to harvest our attention. Over the last century, few times or spaces have remained uncultivated by the 'attention merchants', contributing to the distracted, unfocused tenor of our times. Tim Wu argues that this is not simply the byproduct of recent inventions but the end result of more than a century's growth and expansion…


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Book cover of Trusting Her Duke

Trusting Her Duke by Arietta Richmond,

A Duke with rigid opinions, a Lady whose beliefs conflict with his, a long disputed parcel of land, a conniving neighbour, a desperate collaboration, a failure of trust, a love found despite it all.

Alexander Cavendish, Duke of Ravensworth, returned from war to find that his father and brother had…

Book cover of Nudge: The Final Edition

Emily Lampkin Author Of Duct Tape and White Lies

From my list on transforming how women lead.

Why am I passionate about this?

I’ve spent years working with women who are expected to be confident, decisive, and polished, but are rarely taught how to build those skills. Through my work in politics, public service, and coaching thousands of women, I’ve seen how small, often invisible habits can keep capable women from being fully heard or respected. What I love most is helping women with the practical, everyday moments, like how to say no without apologizing, set boundaries, and build real influence. I’m passionate about leadership because I’ve watched these shifts change careers and lives, and these books reflect the lessons I come back to again and again.

Emily's book list on transforming how women lead

Emily Lampkin Why Emily loves this book

I love this book because it showed me how small adjustments can dramatically increase the chances that people take action.

This was crucial to my knowledge base as a leader because increasing the likelihood someone takes the action you want them to take is a keystone skill of leaders. This book really helped me increase my power as a leader by becoming a better connector.

Overall, it showed me how simple and easy to implement “nudges” can change outcomes. 

By Richard H. Thaler , Cass R. Sunstein ,

Why should I read it?

6 authors picked Nudge as one of their favorite books, and they share why you should read it.

What is this book about?

*Once again a New York Times bestseller! First the original edition, and now the new Final Edition*

An essential new edition revised and updated from cover to cover of one of the most important books of the last two decades, by Nobel Prize winner Richard H. Thaler and Cass R. Sunstein

More than 2 million copies sold

Since the original publication of Nudge more than a decade ago, the title has entered the vocabulary of businesspeople, policy makers, engaged citizens, and consumers everywhere. The book has given rise to more than 400 "nudge units" in governments around the world and…


Book cover of Duct Tape Marketing  The World's Most Practical Small Business Marketing Guide

Jackie Jarvis Author Of Quick Wins in Sales and Marketing: 50 inspiring ideas to grow your business

From my list on marketing strategies for small business owners.

Why am I passionate about this?

As a business development coach and mentor with a strong background in sales and marketing roles in the SME and small business world, I have always been passionate about learning as much as I can about what works well in sales and marketing. Practicing what I preach has always been important, and I love books that align with my belief that sales and marketing need not be complex or onerous to get results. From my experience Small Business Owners do not have the band width to wade through complex marketing speak, they appreciate it when it is straight forward and simple. 

Jackie's book list on marketing strategies for small business owners

Jackie Jarvis Why Jackie loves this book

I love this book because it provides a step-by-step guide and is focused on low-cost, practical strategies. I have recommended it to many of my small and medium business owner clients. I also love that it covers how to be a content marketing expert and an authority in your field, as well as social media and other simple lead-generation tools. 

This book is very readable and offers a lot of simple ideas that are doable. I love the Duct Tape title as it gets a strong message across simply–Duct Tape is simple and effective; we all know that, and it makes the point that just like Duct Tape, marketing can be too. 

By John Jantsch ,

Why should I read it?

2 authors picked Duct Tape Marketing The World's Most Practical Small Business Marketing Guide as one of their favorite books, and they share why you should read it.

What is this book about?

In his trusted book for small businesses, John Jantsch challenges you to craft a marketing strategy that is as reliable as the go-to household item we all know, love, and turn to in a pinch: duct tape.

As a renowned marketing guru and small business coach, John Jantsch has become a leading advisor on how to build and grow a thriving business. Duct Tape Marketing shows you how to develop and execute a marketing plan that yields more revenue and ensures the longevity of small businesses.

Taking a strategic, systemic approach to marketing rather than being constantly won over to…


Book cover of How to Write Sales Letters That Sell

Ian Brodie Author Of Email Persuasion: Captivate and Engage Your Audience, Build Authority and Generate More Sales With Email

From my list on small business marketing.

Why am I passionate about this?

I'm a writer and consultant on marketing and creating online courses. I’m obsessed with “cracking the marketing code.” Ever since I saw firsthand what a huge impact even small marketing changes could have on a business's success I’ve been determined to figure out what the really big impact but low workload changes are. I’ve written about some of them in my book Email Persuasion and I share others in my blogs and videos.

Ian's book list on small business marketing

Ian Brodie Why Ian loves this book

David Ogilvy said, “Drayton Bird knows more about direct marketing than anyone in the world,” and you can see why he said it in this book.

At some point in your marketing you need to get your potential customers to become paying customers. To actually part with their hard-earned cash. This book is a masterclass on how to do that in print – either on your website or in letters, adverts, brochures, or flyers. Bird’s writing has that amazing quality of charm, of being able to get you to buy without feeling you’ve been sold to. The book shows you how to get something similar yourself and is chock full of examples to learn from.

By Drayton Bird ,

Why should I read it?

1 author picked How to Write Sales Letters That Sell as one of their favorite books, and they share why you should read it.

What is this book about?

The right piece of direct mail can produce excellent response rates and have an extraordinary effect on business. But why do some sale letters achieve spectacular results whilst others are instantly consigned to the bin? This book reveals the secrets of creating successful sales letters. Containing examples of real sales letters, it includes plenty of advice on what to avoid as well as what to include. Key topics are covered such as: the secrets of persuasion; planning a letter which will get replies; creating offers that get responses and timing mailings for maximum effect.


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Book cover of Aggressor

Aggressor by FX Holden,

It is April 1st, 2038. Day 60 of China's blockade of the rebel island of Taiwan.

The US government has agreed to provide Taiwan with a weapons system so advanced that it can disrupt the balance of power in the region. But what pilot would be crazy enough to run…

Book cover of Captivology: The Science of Capturing People's Attention

Ian Brodie Author Of Email Persuasion: Captivate and Engage Your Audience, Build Authority and Generate More Sales With Email

From my list on small business marketing.

Why am I passionate about this?

I'm a writer and consultant on marketing and creating online courses. I’m obsessed with “cracking the marketing code.” Ever since I saw firsthand what a huge impact even small marketing changes could have on a business's success I’ve been determined to figure out what the really big impact but low workload changes are. I’ve written about some of them in my book Email Persuasion and I share others in my blogs and videos.

Ian's book list on small business marketing

Ian Brodie Why Ian loves this book

Of all the marketing challenges facing us today, the biggest by far is the immensely difficult task of getting and keeping the attention of our target customers in a ridiculously noisy world.

Captivology isn’t necessarily a marketing book per se. But it’s the best guide to the art and the science of capturing attention. It shows you what gets people to take notice of something, to pay it deeper attention, and then to keep coming back and devoting time to it. You can apply these lessons across all your marketing and of all the marketing ideas and concepts I’ve come across in the last decade, this one has had the deepest and most positive impact on me and the results in my business.

By Ben Parr ,

Why should I read it?

1 author picked Captivology as one of their favorite books, and they share why you should read it.

What is this book about?


Why are we captivated by sites like Facebook and Instagram, but couldn't care less about MySpace Why do some musicians grow as popular as Beyonce, while others never make the charts Why do some nonprofits, such as Charity: Water, succeed in getting our donations, while other charities are ineffective And why can't anyone seem to ever get the attention of their kids

In Captivology, Ben Parr, former editor of Mashable and cofounder of DominateFund, reveals how and why our mind pays attention to some events, ideas, or people and not others. Vividly bringing to life the stories of entrepreneurs, musicians,…


Book cover of Difficult Conversations: How to Discuss What Matters Most
Book cover of Thinking, Fast and Slow
Book cover of Mindset: The New Psychology of Success

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