Difficult Conversations in Family Businesses and Family Offices
Christina Wing joins The Mack Podcast with Brian Adams
Wingspan Founder Christina Wing recently appeared on The Mack Podcast with host Brian Adams for a compelling discussion titled Difficult Conversations in Family Businesses and Family Offices. Drawing on both personal experience and years of teaching and advising, Christina explored why enterprising families avoid tough conversations, and what happens when they don’t have them.
She began by sharing her own story. Christina grew up in a family business where difficult topics – succession, wealth, governance – were never discussed. Just as she was preparing to join the business, her father passed away suddenly, leaving her to untangle a web of decisions they had never made together. “My message is: start talking,” she says.
Why Families Avoid the Hard Stuff
Families often stick to safe topics: food, sports, accomplishments. But essential issues – estate planning, roles, expectations – are often left unspoken. Christina explains that Rising Gen family members may want clarity but hesitate to ask, fearing they’ll sound entitled. A small shift in language can help. Instead of asking, “What am I getting?” try, “What are my responsibilities if something happens to you?”
Left unaddressed, these unspoken questions fester, leading to resentment, miscommunication, and emotionally charged conversations at the worst possible moments.
A Better Way to Begin
Christina offers simple but powerful advice for starting difficult conversations:
Don’t surprise people. Send a message the day before with enough detail to allow time for reflection. Pick a neutral setting; not a formal office across a big desk.
Lead with shared goals. Whether it’s improving a relationship, strengthening the business, or preparing the Rising Gen, aligning on intent changes the tone.
Know the difference. Venting is emotional release. A difficult conversation is an act of care; it’s rooted in a desire to make things better.
Should You Bring in an Advisor?
Sometimes an outside professional is needed, but Christina cautions families not to rush it. The initial conversation should still start within the family. If it’s clear that a facilitator is necessary, the key is finding someone who fits, not just technically, but generationally and interpersonally. “If Generation 2 hires someone Generation 1 doesn’t trust, you’re doomed from the beginning.”
Generational and Cultural Misfires
Communication styles vary widely across generations. Christina tells the story of a Middle Eastern family where G1 felt ignored by G3, only to learn that the younger generation had been sending WhatsApp messages that went unopened. The issue wasn’t disrespect. It was a gap in platforms and expectations.
She also recounts a family that resisted creating an in-law employment policy, until one family member got engaged and a dispute erupted. A talented Rising Gen ended up distancing himself from the business entirely. Christina’s mantra: Policies before it’s personal.
What Families Are Grappling With Today
Christina sees two pressing issues across many of the families she works with:
Clarifying roles. Many families need help distinguishing between owner-operators and owner-investors. Not everyone should work in the business, but everyone should understand their responsibilities as owners.
Geographic dispersion. As families spread out globally, staying connected to the business – and each other – requires more effort than ever.
Christina’s Takeaway
“If someone is having a difficult conversation with you,” she says, “it’s out of kindness. Give it a chance. It can lead to something better. If you don’t try, it won’t get better.”
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🎧 Listen to Christina’s and Brian’s conversation on Apple Podcasts or Spotify.
