Fans pick 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 12,000+ 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

Diana Finch Author Of Value Beyond Money: An Exploration of The Bristol Pound and The Building Blocks for An Alternative Economic System

From my list on our thought-provoking socio-economic system.

Why am I passionate about this?

All my life, I’ve been aware that there are many layers to reality, many of which are human fabrications. Some are physical, like roads. Some are social, like healthcare. But the ones that control our lives the most, and that determine our global outcomes (poverty, war and ecological degradation for example), are ideological. The most powerful of these is our economic system. If we are to address the meta-crisis, I feel passionately that we need to be able to question and reimagine the economy. All the books I’ve chosen have been really important in helping me to think differently about things we usually take for granted.

Diana's book list on our thought-provoking socio-economic system

Diana Finch Why did Diana love this book?

I love this book because of how beautiful and hopeful it is. The author pulls together amazing stories from her life to gradually weave an understanding of the meta-crisis we find ourselves in. I was captivated by the way she contrasts her family’s indigenous American culture with our modern approaches to both science and the economy.

I love Robin’s prose, which is exquisitely written. But perhaps what I value the most is the fact that she writes with optimism, giving me the courage to get up every day and think about how to put her wisdom into practice.

By Robin Wall Kimmerer,

Why should I read it?

53 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

Louis V. Clark III Author Of How to Be an Indian in the 21st Century

From my list on understanding each other in a troubled world.

Why am I passionate about this?

I was born on the Oneida reservation in Wisconsin. Raised during the often troubled, often wonderful decade of the 1960s, I learned to stand up for what I thought was right. I joined forces with my beautiful wife during our high school years, and together, we ran away to build our own life aided by the Oneida principle of “looking ahead seven generations.” Encountering many obstacles along the way, including a poetry professor who said that what I wrote wasn’t poetry and a theater professor who said that if what I wrote was any good it was already being done. Still, I continue to write.

Louis' book list on understanding each other in a troubled world

Louis V. Clark III Why did Louis love this book?

I loved this book because the author was able to share the racist encounters that she had to deal with and the racist encounters all minorities deal with at one time or another. This book puts a new intellectual perspective on those types of happenings. They also illustrated many racist encounters that are all too common and yet hard to believe. A must-read for all.

By Isabel Wilkerson,

Why should I read it?

17 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

Paula Lehman-Ewing Author Of Reimagining the Revolution: Four Stories of Abolition, Autonomy, and Forging New Paths in the Modern Civil Rights Movement

From my list on easing you out of your comfort zone.

Why am I passionate about this?

Throughout my career as a journalist and social documentarian, I have been committed to exposing injustices and seeking out stories overlooked by mainstream media. As my career has evolved in this space—from journalist to grassroots organizer to author—I have learned to remain curious and teachable, acknowledging that my preconceived notions of the world will not do me any good. In confronting the uncomfortable in pursuit of truth, I have uncovered systemic abuses in the criminal justice system and shed light on the harsh realities faced by incarcerated individuals.

Paula's book list on easing you out of your comfort zone

Paula Lehman-Ewing Why did Paula love this book?

Smith offers an up-close-and-personal tour of how the history of slavery has been preserved in various corners of the Earth. From Monticello Plantation in Virginia to the House of Slaves in Gorée Island (Senegal), I was taken on an eye-opening, albeit sometimes cringeworthy, journey through modern-day perceptions of a haunted past.

For me, this retelling of history is most fascinating. It forces the reader to reckon with the idea that truth isn’t just in the eye of the beholder but in the mouth of the teller. How can we find truth in history if it is being told in so many ways? I weirdly enjoyed wrestling with it as I ventured through the places Smith visited as if his storytelling was escorting me.

By Clint Smith,

Why should I read it?

12 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…


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Book cover of Who Will Take Care of Me When I'm Old?: Plan Now to Safeguard Your Health and Happiness in Old Age

Who Will Take Care of Me When I'm Old? by Joy Loverde,

Everything you need to know to plan for your own safe, financially secure, healthy, and happy old age.

For those who have no support system in place, the thought of aging without help can be a frightening, isolating prospect. Whether you have friends and family ready and able to help…

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 That's Not What I Meant!: How Conversational Style Makes or Breaks Relationships

Kieran File Author Of How Language Shapes Relationships in Professional Sports Teams: Power and Solidarity Dynamics in a New Zealand Rugby Team

From my list on expanding your knowledge of how language works.

Why am I passionate about this?

I’ve been fascinated by the power of language for as long as I can remember. As a sociolinguist, I study how language shapes our relationships, identities, and the societies we live in. I’ve spent years analyzing how people communicate in high-pressure environments like professional sports, but my passion for this topic goes far beyond my research. Language is everywhere—it’s how we connect, influence, and make sense of the world. The books on this list have deepened my understanding of the profound ways language impacts our lives. I’m excited to share them with you and hope they inspire you to see language in a whole new light!

Kieran's book list on expanding your knowledge of how language works

Kieran File Why did Kieran love this book?

This book really drew me to the power of language because it completely changed the way I think about everyday conversations and their power to shape relationships. Tannen’s exploration of conversational style taught me that it is not just what we say but how we say it that shapes our relationships. Misunderstandings I’d brushed off made sense: the clashes between my need to be direct and others' preference for subtlety, for example, or why certain conversations left me feeling unheard.

This book was empowering and humbling at the same time. It offers a guide to better communication that doesn’t point fingers but helps you see the nuance in every exchange. If you’ve ever asked, “Why did they take that the wrong way?” this book will resonate.

By Deborah Tannen,

Why should I read it?

1 author picked That's Not What I Meant! as one of their favorite books, and they share why you should read it.

What is this book about?

“Tannen combines a novelist’s ear for the way people speak with a rare power of original analysis....Fascinating.”
—Oliver Sacks, author of The Man Who Mistook His Wife for a Hat and The Mind’s Eye

In That’s Not What I Meant!, Deborah Tannen, renowned communication expert and author of the New York Times bestsellers You’re Wearing THAT? and You Just Don’t Understand, explores how conversational styles can make or break interpersonal relationships at home, at work, or at play. Fans of her books and the healthily curious reader interested in popular psychology, feminism, linguistics, or social sciences will be fascinated by…


Book cover of Honest Dialogue: Presence, Common Sense, and Boundaries When You Want to Help Someone

Ilse Sand Author Of Confronting Shame: How to Understand Your Shame and Gain Inner Freedom

From my list on helping you to be authentic and true to yourself.

Why am I passionate about this?

I am a psychotherapist and pastor. Since my first book Highly Sensitive People in an Insensitive World, which became an international bestseller, I have received letters from all over the world, from people, telling me about their lives. I discovered there is a need for books on how to live your life in an authentic way. I have studied Psychiatrist C.G. Jung and Philosopher Søren Kierkegaard at the university. The books, I recommend are easier to read than these two. In my books, I use many examples. It is important to me that the wisdom of great writers becomes accessible to all people regardless of their level of education.

Ilse's book list on helping you to be authentic and true to yourself

Ilse Sand Why did Ilse love this book?

Bent Falk writes so clearly and touches people. My students are always grateful to me for making them aware of his book. I still read in it now and then. It helps me accept things as they are and my feelings as they are. And it helps me be authentic and true to myself in my relations.

By Bent Falk,

Why should I read it?

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

What is this book about?

Focusing on how someone in need can best be helped, the author identifies the skills and honesty of the person who wants to help as key to how effective this can be. Looking in detail at the nature of boundaries, willingness to speak from a place of authenticity and to be honestly present to the experience of the individual person, and the sensitive and economical use of language, the author shows how people in a state of deep personal crisis can be richly helped. Taking the view that no set response is always right or always wrong, he argues strongly…


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

Why am I passionate about this?

I’ve said all along that the people I’ve surrounded myself with are the most important part of everything I do - my crew is what helps push me forward and supports me when things are tough. It’s a really important skill to have to continually do two things: better understand myself, through both outside learning and deepening self-awareness, and continue to learn about other people and strengthen all of the relationships I have, both inside and outside of business.

Helaine's book list on business books for digging into your relationship with yourself and others - which is the key to success

Helaine Knapp Why did Helaine love this book?

I feel that understanding and being able to work with all kinds of people is really the key to success in business (and honestly, in life in general). I consider myself a damn good communicator, but I still learned SO much in this book to take my leadership in that area to the next level.

It’s also not just about speaking and relationships, but taking in all of the cues in situation (verbal, visual, context, etc). This should be required reading for anyone working with people (which is most of us!). 

By Vanessa Van Edwards,

Why should I read it?

3 authors 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 Douglas Stone, Bruce Patton, 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 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…


Book cover of Braiding Sweetgrass: Indigenous Wisdom, Scientific Knowledge and the Teachings of Plants
Book cover of Caste: The Origins of Our Discontents
Book cover of How the Word Is Passed: A Reckoning with the History of Slavery Across America

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5 book lists we think you will like!

Interested in interpersonal communication, conversation, and empathy?

Conversation 12 books
Empathy 166 books