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

Aymar Jean Escoffery Author Of Reparative Media

From my list on finding your personal AI: Ancestral Intelligence.

Why am I passionate about this?

I used to think of television as a third parent. As a child of immigrants, I learned a lot about being an American from the media. Soon, I realized there were limits to what I could learn because media and tech privilege profit over community. For 20 years, I have studied what happens when people decide to make media outside of corporations. I have interviewed hundreds of filmmakers, written hundreds of blogs and articles, curated festivals, juried awards, and ultimately founded my own platform, all resulting in four books. My greatest teachers have been artists, healers, and family—chosen and by blood—who have created spaces for honesty, vulnerability, and creative conflict.

Aymar's book list on finding your personal AI: Ancestral Intelligence

Aymar Jean Escoffery Why Aymar loves this book

This book helped me release shame after a colleague of mine told me my work wasn’t “science.”

Here’s the truth: to create a healing platform, I needed to tap into ways of thinking that academia sees as “woo woo” and “savage.” I looked to the stars. I meditated. I did rituals and read myths.

Dr. Kimmerer, trained as a traditional botanist, realized that the Indigenous myths and stories she was told as a child contained scientific knowledge passed down for generations by her tribe.

She realized there were scientific truths her community knew for millennia that traditional scientists only discovered within the last 100 years. This is the power of Ancestral Intelligence, disregarded by the same science that ultimately created AI.

What stories, fables, and myths have taught you valuable lessons about the world?

By Robin Wall Kimmerer ,

Why should I read it?

59 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…


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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 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 Louis loves 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?

20 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 Paula loves 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?

13 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 The Guardian of the Palace

The Guardian of the Palace by Steven J. Morris,

The Guardian of the Palace is the first novel in a modern fantasy series set in a New York City where magic is real—but hidden, suppressed, and dangerous when exposed.

When an ancient magic begins to leak into the world, a small group of unlikely allies is forced to act…

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 Melinda loves 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

Kate Somerset Author Of Mom... You Just Need to Get Laid

From my list on becoming a memorable connector.

Why am I passionate about this?

Whether writing under my pen name Kate Somerset, or showing up as Ann Louden in real life, I've always believed in the enriching value of making memorable connections. As a consultant to nonprofits, I emphasize it’s not the number of donors that guarantees philanthropic support. It’s the quality of relationships with the organization. The deeper the connections, the more likely that donors will significantly invest and re-invest. As a breast cancer survivor/spokesperson, I know the importance of having a support team. And as an author and relationship coach, I emphasize establishing trust in relationships. The books on this list describe how you can be a connector, each with uniquely valuable content. I hope you find them all meaningful!

Kate's book list on becoming a memorable connector

Kate Somerset Why Kate loves this book

When I read this book, the lightbulb went off. I have been in so many situations where I didn’t feel heard, but I couldn’t quite put my finger on why.

Sorenson explains that truly being connected happens only when we are validated. I never realized that almost every conversation we have is a bid for validation. We are asking others not just to hear us but also to “say something.”

The response can either be positive or engageda turning towards usOR negative or passivea turning away from us. I couldn’t have put it into these exact words, but I now know that being understood is one of the greatest of human needs and is often unmet. The book underscores that connections happen best through validation. 

By Michael S. Sorensen ,

Why should I read it?

3 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 Kieran loves 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…


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Book cover of Oaky With a Hint of Murder

Oaky With a Hint of Murder by Dawn Brotherton,

Aury and Scott travel to the Finger Lakes in New York’s wine country to get to the bottom of the mysterious happenings at the Songscape Winery. Disturbed furniture and curious noises are one thing, but when a customer winds up dead, it’s time to dig into the details and see…

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 Helaine loves 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

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 
·…


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 Aryanne loves 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,…


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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 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 Ilse loves 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 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 175 books