100 books like How to Have Impossible Conversations

By Peter Boghossian, James Lindsay,

Here are 100 books that How to Have Impossible Conversations fans have personally recommended if you like How to Have Impossible Conversations. Shepherd is a community of 10,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Braiding Sweetgrass: Indigenous Wisdom, Scientific Knowledge and the Teachings of Plants

Shannan Martin Author Of Start with Hello: (And Other Simple Ways to Live as Neighbors)

From my list on cultivating empathy and connection in a divided world.

Why am I passionate about this?

A dozen years ago, my family moved from a homogeneous community where everyone looked, lived, and believed as we did to a vibrant neighborhood filled with difference and complexity. This shifted something deep inside me and ultimately changed the way I see the world and myself within it. It set me on a path toward understanding how authentic, ordinary community holds the power to transform our world. To live as neighbors is to draw near to each other. I have written three books on this central theme and plan to spend the rest of my life reaching for empathy as our best tool in reclaiming the goodness of humanity.  

Shannan's book list on cultivating empathy and connection in a divided world

Shannan Martin Why did Shannan love this book?

This book is an instant classic. It took me years to finish reading it because I did not want it to end.

Kimmerer’s writing appealed to the dreamer in me while also explaining the science of the natural world in ways that were unforgettable. This beautifully written book connected me to my physical home and the people around me. I will come back to it again and again. 

By Robin Wall Kimmerer,

Why should I read it?

45 authors picked Braiding Sweetgrass as one of their favorite books, and they share why you should read it.

What is this book about?

Called the work of "a mesmerizing storyteller with deep compassion and memorable prose" (Publishers Weekly) and the book that, "anyone interested in natural history, botany, protecting nature, or Native American culture will love," by Library Journal, Braiding Sweetgrass is poised to be a classic of nature writing. As a botanist, Robin Wall Kimmerer asks questions of nature with the tools of science. As a member of the Citizen Potawatomi Nation, she embraces indigenous teachings that consider plants and animals to be our oldest teachers. Kimmerer brings these two lenses of knowledge together to take "us on a journey that is…


Book cover of Caste: The Origins of Our Discontents

Melinda Lewis Author Of Social Policy for Effective Practice: A Strengths Approach

From my list on igniting students’ passions about policy change.

Why am I passionate about this?

I am a policy advocate, grassroots activist, university professor, and author committed to social change—at scale—to advance social work values of racial, economic, environmental, and social justice. Recognizing that most social workers are drawn to our profession because they want to make a difference in the lives of their clients, one by one, I invest my energies and skills to making policy study and practice accessible, relevant, and urgent. My students quickly get used to noting the book recommendations I sprinkle throughout class discussions and in assignment feedback, because when you see the world through a social policy frame, everything has a policy implication! 

Melinda's book list on igniting students’ passions about policy change

Melinda Lewis Why did Melinda love this book?

Wilkerson’s scholarship on race and injustice is certainly not a secret, but I still find some colleagues who have not yet read this book.

To convince people to pick it up, I promise that its language is poetic and imminently accessible, and I share the two pieces that have remained top of mind for years: first, Wilkerson’s research about the lessons Nazi Germany took from the racial caste system of Jim Crow United States, and second, the way she crafts an analogy of a crumbling house to make the case for reparations for racist harm, which—like cracks in the foundation of a house you just bought—may not be your fault but are still your problem.

I am forever grateful to Wilkerson for gifting us her insights and rhetorical tools, conveyed so skillfully in this tremendous contribution.

By Isabel Wilkerson,

Why should I read it?

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

What is this book about?

THE TIME NONFICTION BOOK OF THE YEAR | #1 NEW YORK TIMES BESTSELLER

"Powerful and timely ... I cannot recommend it strongly enough" - Barack Obama

From one of America's most celebrated and insightful writers, the moving, eye-opening bestseller about what lies hidden under the surface of ordinary lives

In this brilliant book, Isabel Wilkerson gives us a masterful portrait of an unseen phenomenon in America as she explores, through an immersive, deeply researched narrative and stories about real people, how America today and throughout its history has been shaped by a hidden caste system, a rigid hierarchy of human…


Book cover of How the Word Is Passed: A Reckoning with the History of Slavery Across America

Shannan Martin Author Of Start with Hello: (And Other Simple Ways to Live as Neighbors)

From my list on cultivating empathy and connection in a divided world.

Why am I passionate about this?

A dozen years ago, my family moved from a homogeneous community where everyone looked, lived, and believed as we did to a vibrant neighborhood filled with difference and complexity. This shifted something deep inside me and ultimately changed the way I see the world and myself within it. It set me on a path toward understanding how authentic, ordinary community holds the power to transform our world. To live as neighbors is to draw near to each other. I have written three books on this central theme and plan to spend the rest of my life reaching for empathy as our best tool in reclaiming the goodness of humanity.  

Shannan's book list on cultivating empathy and connection in a divided world

Shannan Martin Why did Shannan love this book?

As someone raised in small-town USA, I had to come to terms with the fact that I was taught a white-washed, largely inaccurate American history. It was up to me to re-educate myself.

As someone who can get bogged down by long lists of dates and details, How the Word is Passed gave me a modern lens for understanding the history around slavery. I was gripped by Smith’s lyrical, humane approach.

This is the sort of book that makes the world better.   

By Clint Smith,

Why should I read it?

9 authors picked How the Word Is Passed as one of their favorite books, and they share why you should read it.

What is this book about?

ONE OF BARACK OBAMA'S FAVOURITE BOOKS OF THE YEAR
A NUMBER ONE NEW YORK TIMES BESTSELLER
LONGLISTED FOR THE NATIONAL BOOK AWARD FOR NON-FICTION

'A beautifully readable reminder of how much of our urgent, collective history resounds in places all around us that have been hidden in plain sight.' Afua Hirsch, author of Brit(ish)

Beginning in his hometown of New Orleans, Clint Smith leads the reader on an unforgettable tour of monuments and landmarks - those that are honest about the past and those that are not - which offer an intergenerational story of how slavery has been central in…


Book cover of A Knock at Midnight: A Story of Hope, Justice, and Freedom

Melinda Lewis Author Of Social Policy for Effective Practice: A Strengths Approach

From my list on igniting students’ passions about policy change.

Why am I passionate about this?

I am a policy advocate, grassroots activist, university professor, and author committed to social change—at scale—to advance social work values of racial, economic, environmental, and social justice. Recognizing that most social workers are drawn to our profession because they want to make a difference in the lives of their clients, one by one, I invest my energies and skills to making policy study and practice accessible, relevant, and urgent. My students quickly get used to noting the book recommendations I sprinkle throughout class discussions and in assignment feedback, because when you see the world through a social policy frame, everything has a policy implication! 

Melinda's book list on igniting students’ passions about policy change

Melinda Lewis Why did Melinda love this book?

Social work students are people people, so even with the interactive cases and vignettes that connect policy knowledge to practice, it can be difficult for students planning for a career in interpersonal therapy or crisis intervention to connect emotionally to complex policy topics like Social Security reform, net-zero carbon emissions, or criminal justice reform.

Barnett’s non-fiction title on the latter topic is page-turning and infused with heart. It also relates her activism and community organizing, in service of advancing justice in policing and corrections.

This part of her story helps students see how they, too, can take actions—even as an individual—that bear witness to our values and advance toward a vision of social change.

By Brittany K. Barnett,

Why should I read it?

1 author picked A Knock at Midnight as one of their favorite books, and they share why you should read it.

What is this book about?

LOS ANGELES TIMES BOOK PRIZE FINALIST • NAACP IMAGE AWARD NOMINEE • A “powerful and devastating” (The Washington Post) call to free those buried alive by America’s legal system, and an inspiring true story about unwavering belief in humanity—from a gifted young lawyer and important new voice in the movement to transform the system.

“An essential book for our time . . . Brittany K. Barnett is a star.”—Van Jones, CEO of REFORM Alliance, CNN Host, and New York Times bestselling author 

Brittany K. Barnett was only a law student when she came across the case that would change her…


Book cover of I Hear You: The Surprisingly Simple Skill Behind Extraordinary Relationships

Lida Citroën Author Of Success After Service: How to Take Control of Your Job Search and Career After Military Duty

From my list on success in a civilian life after the military.

Why am I passionate about this?

I’m an executive coach, personal branding consultant, and reputation management expert helping global executives, entrepreneurs, and thought leaders manage how they’re perceived and drive towards ideal opportunities. A long-time passionate supporter of the military, I volunteer to help veterans transitioning to civilian careers. My work with veterans comes from gratitude for their sacrifice. I regularly speak at military installations, podcasts, and events on veteran transition and hiring, teach in the TAP program at the US Air Force Academy, and serve on the Board of Directors at Project Sanctuary, which focuses on healing military families. Since 2012, I’ve also been a writer for Military.com.

Lida's book list on success in a civilian life after the military

Lida Citroën Why did Lida love this book?

There are so many books written about active listening and communications, but not many that focus on what the other person really needs: Validation.

As veterans re-integrate into the civilian workforce and lifestyle, the way they communicate is different from when they were serving in the military, and becoming mindful of how they communicate with others is important. This book will guide them through a key skill (validation) that will help them not only in their career, but also in their personal life. 

By Michael S. Sorensen,

Why should I read it?

2 authors picked I Hear You as one of their favorite books, and they share why you should read it.

What is this book about?

What if making one tweak to your day-to-day conversations could immediately improve every relationship in your life?

In this 3-hour, conversational read, you’ll discover the whats, whys, and hows of one of the most valuable (yet surprisingly little-known) communication skills available—validation. 

Whether you’re looking to improve your relationship with your spouse, navigate difficult conversations at work, or connect on a deeper level with friends and family, this book delivers simple, practical, proven techniques for improving any relationship in your life.

Mastery of this simple skill will enable you to:

Calm (and sometimes even eliminate) the concerns, fears, and uncertainties of…


Book cover of Cues: Master the Secret Language of Charismatic Communication

Jenny Foss Author Of Do This, Not That: Career

From my list on taking charge of your career.

Why am I passionate about this?

As a kid, I dreamed of becoming a California beach lifeguard. Considering I grew up in Michigan, this was a rather aspirational choice. To my parents’ relief, my career goals shifted over time, as I realized my gift for writing. I became a journalist then went into marketing. But after years of cranking out corporate content, I (sadly) burned out on it, dropped everything, and became a recruiter. Within months, I missed writing – so much so that I started a career-related blog, which became a thriving business dedicated to helping people move their careers forward. Gratefully, this work led to an amazing assignment, writing Do This, Not That: Career

Jenny's book list on taking charge of your career

Jenny Foss Why did Jenny love this book?

I devoured body language expert Vanessa Van Edwards’ first book, Captivate, and was thrilled when I learned that she’d written Cues. What I love about Vanessa’s writing, and particularly this book, is that she makes scientific research (in this case, research on how to become more charismatic) interesting, easy to digest, and (importantly!) actionable.

It’s a great read for anyone who finds themselves struggling to connect with and engage others in the workplace, at interviews, or in day-to-day life. The book teaches you the cues that will help you be more charismatic in any setting.

By Vanessa Van Edwards,

Why should I read it?

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

What is this book about?

It's not enough to have great ideas. You also need to know how to communicate them.

What makes someone charismatic? Why do some people captivate a room, while others have trouble managing a small meeting? What makes some ideas spread, while other good ones fall by the wayside?

Cues - the tiny signals we send to others 24/7 through our body language, facial expressions, word choices and vocal inflection - have a massive impact on how we, and our ideas, come across. Our cues can either enhance our message or undermine it.

In this entertaining and accessible guide to the…


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

Bret Lyon Author Of Embracing Shame: How to Stop Resisting Shame and Turn It into a Powerful Ally

From my list on healing shame and trauma.

Why am I passionate about this?

I spent many years deeply angry at my parents and not really understanding why. When I found out about shame, and how it was passed down from generation to generation, I was finally able to crack the code. Their “permissiveness” was actually neglect. Without meaning to, they had put their shame on me and I was still suffering from not really being seen. I made it my mission to help others heal their shame so they can be better people and better parents, and live fuller lives. I am the co-director of the Center for Healing Shame and co-author of Embracing Shame.

Bret's book list on healing shame and trauma

Bret Lyon Why did Bret love this book?

I love this book because it says that all conversations take place on 3 different levels. 

There is the content level, the most obvious; the emotional level, how important the subject is and the emotions around it; and the internal level of “what does this conversation say about me,” which is the shame level. This level may be the most important and the most hidden.

By Bruce Patton, Douglas Stone, Sheila Heen

Why should I read it?

7 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 
·…


Book cover of How to Use Power Phrases to Say What You Mean, Mean What You Say, & Get What You Want

Aryanne Oade Author Of Bullying in Teams: How to Survive It and Thrive

From my list on workplace bullying.

Why am I passionate about this?

Aryanne Oade works as a chartered psychologist, executive coach, and author of eight books. She has over thirty years’ experience in guiding clients through the challenge of complex workplace dynamics, and specialises in enabling detoxification and recovery from workplace bullying. Author of the best-selling award-winner Free Yourself from Workplace Bullying: Become Bully-Proof and Regain Control of Your Life, Aryanne’s work and books have been featured in The Independent, Sunday Independent (Ireland), Psychologies, Marie Claire, Good Housekeeping, The Belfast Telegraph, HR Magazine, Safety & Health Practitioner, SHP Online, Nursing Times, and Midwives.

Aryanne's book list on workplace bullying

Aryanne Oade Why did Aryanne love this book?

I love the simplicity of this book. I recommend it to clients who have a hard time being assertive. The book gives straightfoward, no nonsense input on how to handle a variety of challenging situations in a way which is both self-protective and likely to enable the reader to get a favourable outcome. Situations include how to say no without alienating the other person; asking in a way which makes it likely you’ll get what you want; and dealing with putdowns or unjust criticism.

By Meryl Runion,

Why should I read it?

1 author picked How to Use Power Phrases to Say What You Mean, Mean What You Say, & Get What You Want as one of their favorite books, and they share why you should read it.

What is this book about?

Get to the point! Learn how to use Power Phrases to say what you mean...and get what you want. If you have ever walked away from a situation because you didn't know what to say, or you didn't know what to say but you spoke anyway, you know about all the stress, confusion, wasted time, missed opportunities, and hurt feelings you could have avoided if only you'd said the right thing at the right time. Now internationally acclaimed executive coach and communication guru Meryl Runion introduces you to a powerful, easy-to-master communication technology that lets you say what you mean,…


Book cover of Skilled Interpersonal Communication: Research, Theory and Practice

Stuart Hanscomb Author Of Critical Thinking: The Basics

From my list on interpersonal communication and influence.

Why am I passionate about this?

I am an academic at the University of Glasgow with a background in philosophy and psychology. My approach to critical thinking is broad and informed by several other teaching and research interests: emotional intelligence, the psychology of influence, interpersonal communication, and virtue ethics. Motivating much of what I do is the question: How are we to live well? With respect to critical thinking I don’t just deal with the nature and structure of arguments, but also with the role they play in constructive dialogues, and how poor reasoning is linked to psychological biases and the absence of certain virtues. The books I have chosen here are representative of these concerns.

Stuart's book list on interpersonal communication and influence

Stuart Hanscomb Why did Stuart love this book?

As well as being academically sound this book is accessible and engaging, and it deals with subjects such as explaining, listening, assertiveness, negotiations, and persuasion in a way that is highly applied and always useful. Perhaps most importantly it addresses many of the aspects of interpersonal communication that I have for a long time found fascinating and challenging.

By Owen Hargie,

Why should I read it?

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

What is this book about?

-Number one text for depth and comprehensive coverage: detailed analysis of existing knowledge and practice
-Comprehensively updated in 7th edition with latest research findings, theoretical developments and applications to practice.
-Well structured and easily navigable: topic areas clearly defined and packaged to fit course delivery
-Unmatched authority: highly recognized author and five previously successful editions
-Links theory to practice to help students learn and apply key skills
-Offers a strong UK-originated alternative to other US-oriented texts
-Flexible and cross-disciplinary: applies to a broad range of professional roles and contexts


Book cover of Thanks for the Feedback: The Science and Art of Receiving Feedback Well

Lawrence E. Susskind Author Of Good for You, Great for Me: Finding the Trading Zone and Winning at Win-Win Negotiation

From my list on negotiating for mutual advantage.

Why am I passionate about this?

I am a Professor at MIT and co-founder of both the inter-university Program on Negotiation at Harvard Law School and the not-for-profit Consensus Building Institute that provides help in resolving some of the most complex resource management disputes around the world. I have been teaching negotiation and dispute resolution, doing research about the circumstances under which various negotiation strategies do and don’t work, and offering online training for more than four decades. Given the many negotiations I've observed, I’m convinced that negotiating for mutual advantage is the way to go -- avoid unnecessary conflict, get what you want in all kinds of negotiating situations, and walk away with good working relationships and a solid reputation.

Lawrence's book list on negotiating for mutual advantage

Lawrence E. Susskind Why did Lawrence love this book?

Doug and Sheila start with the assumption that we all want to learn and grow, but at the same time, we also want to be accepted just as we are. That means, we don’t want to be on the receiving end of evaluations, advice, criticism, or coaching that highlight our flaws. Most of us believe that feedback is essential for ensuring healthy relationships and ensuring our professional development, but as they point out, “we dread it and often dismiss it.” They see feedback as a step in the larger process of negotiation. When I try to convince you of something, I need to offer not just a demand, but an argument or evidence that makes sense to you and backs up what I’m saying.

Doug and Sheila have suggestions for how to avoid the traps (“triggers,” they call them) that get in the way of our accepting or even seeking…

By Sheila Heen, Douglas Stone,

Why should I read it?

1 author picked Thanks for the Feedback as one of their favorite books, and they share why you should read it.

What is this book about?

The coauthors of the New York Times-bestselling Difficult Conversations take on the toughest topic of all: how we see ourselves

Douglas Stone and Sheila Heen have spent the past fifteen years working with corporations, nonprofits, governments, and families to determine what helps us learn and what gets in our way. In Thanks for the Feedback, they explain why receiving feedback is so crucial yet so challenging, offering a simple framework and powerful tools to help us take on life's blizzard of offhand comments, annual evaluations, and unsolicited input with curiosity and grace. They blend the latest insights from neuroscience and…


5 book lists we think you will like!

Interested in interpersonal communication, conversation, and empathy?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about interpersonal communication, conversation, and empathy.

Interpersonal Communication Explore 37 books about interpersonal communication
Conversation Explore 9 books about conversation
Empathy Explore 140 books about empathy