Let's Talk Family Enterprise

72: Navigating Complexity in Enterprising Families

Oct 28, 2025
Michelle Osry, a family enterprise and governance advisor with a rich background at Deloitte Canada, dives into the nuances of guiding families through complex challenges. She highlights the difference between complicated and complex issues, emphasizing the need for roleplay to better understand family dynamics. Michelle introduces Theory U for spotting future possibilities and shares co-creation strategies fostering unique family solutions. She encourages facilitators to enhance awareness and dialogue, and stresses the importance of humility over just fixing problems.
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ANECDOTE

Simple Role-Play Revealed Complexity

  • Michelle described designing a simple role-play to let attendees experience complexity firsthand.
  • Participants reported sudden empathy and new clarity about family members after the brief exercise.
INSIGHT

Complicated vs. Complex Distinction

  • Complicated problems have many parts but remain predictable with expertise.
  • Complex family dynamics are emergent and require presence, humility, and adaptability rather than just technical skill.
ADVICE

Listen For Emergence, Not Just Answers

  • Listen for what is emerging rather than only applying prior expertise.
  • Be present and open so you can spot new possibilities the family generates together.
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