UNSPEAKABLE: THE TABOO TOPICS WE AVOID AND HOW TO
TALK ABOUT THEM

Unspeakable: The Taboo Topics We Avoid and How to Talk About Them

AVAILABLE

OCT 20

A practical, case-led guide to the sensitive subjects people know matter, but do not feel allowed to raise directly.

Why We Avoid the Conversation

Most people do not avoid important conversations because they do not care.

Often, they avoid them because they care deeply.

They do not ask about a will because they do not want to sound greedy.

They do not raise succession because they do not want to seem disloyal.

They do not name a performance issue because they do not want to embarrass someone.

They do not talk about money because they do not want love to feel transactional.

They do not admit a mistake because they fear it will change how people see them.

So They Wait

So they wait.

They soften the question.

They mention it indirectly.

They talk privately, but not in the room.

They make assumptions.

They hope the right moment will appear.

But the right moment does not always arrive.

What Silence Does

And when a taboo subject stays unspoken, it doesn’t disappear. It metastasizes, distorts decisions, corrodes trust, and shapes outcomes.

This is the territory Christina Wing explores in Unspeakable: The Taboo Topics We Avoid and How to Talk About Them.

The book begins from a simple but powerful observation: some topics are not only difficult. They feel off-limits. They carry too much history, status, fear, grief, identity, love, power, or risk to raise casually. So people work around them, often with the best of intentions.

The Cost of Guessing

The Father
A father avoids talking with his children about money, succession, mortality, and his wishes because those topics feel too uncomfortable to name. Years later, after his funeral, his children receive estate documents they do not understand. What remains is not clarity, but confusion, competing assumptions, and decisions each child has to make without the conversation that should have come before.

The Manager
A manager wants to be considerate of a high-performing woman who has recently returned from parental leave. Rather than ask what she wants, the manager assumes the timing is wrong and passes her over for a senior role. A decision that looked kind from the outside is shaped by guessing instead of conversation.

The Leader
A leader makes a mistake, but delays the apology because admitting fault feels too costly. The silence that follows becomes part of the harm. Trust is not only damaged by what happened; it is damaged by what was not named, owned, or repaired.

Making the Real Topic Discussable

These are the moments at the heart of Unspeakable.

Not dramatic confrontations.

Not perfect speeches.

Not reckless honesty that says everything without considering the cost.

The book is about learning how to make the real topic discussable — with enough care, preparation, and practical judgment for the conversation to begin.

Questions That Open the Door

What is the real topic underneath the formal one?

Why does this subject feel taboo to raise?

What am I assuming because no one has asked?

What might this conversation touch for the other person?

What setting would make the conversation more possible?

What first sentence could open the door without turning the topic into an accusation?

The Subjects We Struggle to Name

Drawing on Christina’s work in business, teaching, family enterprise, advisory rooms, and her own life, Unspeakable explores the sensitive subjects people know matter, but do not always feel allowed to raise directly.

Money. Death. Age. Succession. Mistakes. Fear. Performance. Inheritance. Religion. Politics. Family conflict.

Before Silence Shapes the Outcome

Left unspoken, these topics do not disappear.

They shape decisions.

They strain relationships.

They corrode trust.

They leave people guessing about what was meant, what was intended, and what should happen next.

That is why Unspeakable is not simply a book about difficult conversations.
It is a practical, case-led guide to broaching taboo and sensitive subjects with care, clarity, judgment, and grace.

Through vivid stories, scripts, reflection questions, conversation starters, and practical tools, Christina helps readers build the skill of beginning the conversations they have been avoiding — before silence shapes the outcome for them.

Praise for Unspeakable

Leaders, authors, and thinkers across business, leadership, and organizational life are recognizing Unspeakable as both timely and enduring: a practical guide to the subjects people know matter, but often do not know how to raise.

Christina Wing pairs vivid stories with clear scripts to show us how to talk about money, power, succession, layoffs, politics, and more in ways that build trust rather than secrecy or fear.

Amy C. Edmondson

Novartis Professor of Leadership and Management, Harvard Business School Author, Right Kind of Wrong: The Science of Failing Well (Atria, 2023)

Unspeakable is both profound and practical. It is for everyone who cares about their effectiveness and their legacy.

Jim Koch

Founder, Chairman, CEO and President, Boston Beer Company

Read Unspeakable and start finding the trust and depth you want from your relationships.

Arthur C. Brooks

#1 New York Times bestselling author of The Meaning of Your Life

When we avoid uncomfortable topics, the results can be catastrophic. Professor Wing will help you have the conversations you want to avoid but need to have.

Kim Scott

Author of Radical Candor

I can’t stop talking about Christina Wing’s Unspeakable. This timeless and beautifully written gem helped me understand why it is so hard — and so crucial — to talk about forbidden topics such as money, aging, failure, and family conflict.

Robert I. Sutton

Stanford Professor Emeritus and bestselling author of The No Asshole Rule and The Friction Project

Stories, scripts, questions, and tools you can use in real life.

Stories

Real-world examples from families, organizations, classrooms, leadership teams, and advisory work.

Scripts

Practical language for beginning conversations that people often avoid.

Reflection Questions

Prompts to help readers understand their own resistance, fear, assumptions, and purpose.

Conversation Starters

Scenarios and opening questions that help readers practice before the moment arrives.

Takeaways

Clear, practical summaries at the end of each chapter.

The taboo topics shaping families, careers, teams, and organizations.

Death, Estate Planning, and Inheritance

Why wills, assets, liabilities, sentimental possessions, and end-of-life wishes need clearer conversations.

Work-Family Conflicts

How to talk about the ways life outside work affects work — without guessing behind people’s backs.

Money

Why money carries fairness, control, shame, dependence, belonging, and power.

Fear

How fear shapes workplace behavior, silence, compliance, and the willingness to tell the truth.

Layoffs, Firings, and Unemployment

Why job loss remains shame-laden, and how to talk about it with more honesty and dignity.

Ownership and Governance

Why shared ownership requires rules, roles, decision rights, and the courage to discuss them early.

Race and Religion

How to acknowledge identity, difference, and belonging without reducing people to a single dimension.

Politics

How to stay curious and clear when disagreement feels risky.

How to Have the Conversation

Practical guidance for preparing, beginning, and following through.

For anyone who knows the conversation matters, but does not know how to begin.

UNSPEAKABLE IS FOR:

Leaders

who want to build trust without avoiding hard truths.

Managers

who need to talk about performance, fear, accountability, and work-family constraints.

Founders and family business leaders

navigating succession, ownership, governance, and next-generation readiness.

Families

trying to talk more clearly about wills, inheritance, money, aging, fairness, and responsibility.

Advisors, coaches, consultants, educators, and board members

helping others move through high-stakes decisions.

Professionals

of all ages who want to become more skilled at straight talk.

Learn how to begin the conversations people most often avoid with stories, scripts, questions, and practical tools you can use in real life.

INQUIRY

BRING THE TABOO SUBJECT INTO THE CONVERSATION
WITH CHRISTINA WING

Invite Christina to speak, join a media conversation, or work with your organization on the taboo and sensitive subjects already influencing decisions, relationships, and outcomes.

SPEAKING / MEDIA / PODCAST / BULK ORDERS / PARTNERSHIP / OTHER

info@christinawing.com

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    Unspeakable: The Taboo Topics We Avoid and How to Talk About Them

    AVAILABLE

    OCT 20

    Pre-Order Now

    Available anywhere books are sold