INTERVIEW | Make Money by Having the Conversations Everyone Else Avoids with Christina Wing

Christina Wing is a senior lecturer at Harvard Business School, where she teaches and researches leadership and family enterprise. She created the popular MBA course Demystifying the Family Enterprise and chairs the executive education program Families in Business. She is also the founder of Wingspan Legacy Partners and author of Unspeakable: The Taboo Topics We Avoid and How to Talk About Them. In this episode, Christina shares why relationships and trust can be more valuable than knowledge alone, how difficult conversations can make or break a business, and why leaders need to get comfortable addressing the elephants in the room.

On this episode we talk about:

• The surprising first dollar Christina ever made after pulling a struggling swimmer from a deep-water pool

• Growing up in an entrepreneurial family and moving 18 times before business school

• How Christina went from Wall Street to Harvard Business School

• What Harvard's case method is and why it focuses on practical problem-solving rather than textbooks

• What "family enterprise" means and why it encompasses everything from mom-and-pop businesses to family offices and major family-owned companies

• Why businesses often fail because of poor communication rather than poor business decisions

• The relationship between competence, networking, and trust

• Why "what you know" gets you ready for the room, but "who you know" can get you into the room

• How relationships create the trust necessary to turn knowledge into action

• Why Christina wrote Unspeakable and why the list of topics people avoid discussing keeps growing

• How avoiding conversations about money, politics, religion, promotions, and other sensitive topics can create bigger problems

• The difference between a difficult moment and a difficult conversation

• How to approach uncomfortable conversations without becoming "pre-pissed"

• Why context, timing, neutrality, and setting matter when discussing sensitive subjects

• How Wingspan Legacy Partners helps families and businesses navigate major challenges and execute solutions

• Why Christina believes you can't effectively advise global businesses without understanding their culture firsthand

• The professional and personal benefits of traveling and experiencing different cultures

• Christina's favorite places to visit and the destinations she hopes to explore next

Top 3 Takeaways:

1. Relationships turn competence into opportunity.
Knowing your stuff matters, but knowledge alone doesn't necessarily get you into the room. Christina argues that relationships create access, trust, and ultimately the ability to put your capabilities into action. Building a strong network isn't separate from developing expertise—it helps your expertise actually create opportunities.

2. The conversations you avoid can become the problems you can't solve.
Christina has seen businesses struggle not because they made bad business decisions, but because people failed to communicate about the issues that mattered most. Addressing the "elephant in the room" may be uncomfortable, but avoiding it can prevent organizations and relationships from moving forward.

3. Difficult conversations require preparation, neutrality, and a common goal.
Before jumping into a sensitive conversation, take time to think through what you want to accomplish—but don't overthink it to the point where you become "pre-pissed." Choose a neutral setting, establish expectations, listen without interrupting, and remind everyone involved of the shared goal you're trying to accomplish.

Notable Quotes:

• "What you know demonstrates capability. Who you know gets you in the room to use that capability."

• "Competency isn't the only thing that's gonna build trust."

• "Trust comes through relationships."

• "Very rarely do the businesses I work with fail because of poor business decisions. They fail because of poor communication."

• "If you can get in the room, unearth the elephant and talk about it, you're more likely to survive."

• "Context is everything."

• "When you think too long, you get what I call pre-pissed."

• "You have to be able to talk."

• "You can't solve that without understanding cultural differences."

Connect with Christina Wing:

• Website: ChristinaWing.com

• Book: Pre-Order Unspeakable: The Taboo Topics We Avoid and How to Talk About Them (available Oct 20)

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