Planning for the Inevitable: How Family Offices Can Preserve Legacy Through Transitions

In every family office, turnover is inevitable. A generational shift. A health event. A key advisor stepping away. These moments aren’t just logistical, they’re deeply personal, high-stakes transitions that test whether a family’s knowledge, values, and intentions have been documented and shared.

In a new episode of the Easemakers Podcast, leafplanner founder and CEO Josh Kanter shares how his own family’s story shaped his approach to helping families navigate these pivotal transitions, and why he built leafplanner to prevent others from going through what he did unprepared.

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From Personal Loss to Purpose-Built Platform

When Josh’s father was diagnosed with cancer, Josh stepped into the family office and spent 18 months shadowing him, trying to learn everything he could. Even with that time and access, he still felt unprepared. That gap between proximity and preparedness became the seed of leafplanner.

“If I felt unready after 18 months working side by side,” Josh says, “what does that mean for families who don’t have the benefit of time, or a clear roadmap?”

leafplanner was born out of that experience, a way to help other families capture and communicate the knowledge that too often lives only in people’s heads.

What Families Miss During Transition

In the podcast, Josh highlights three core issues that surface during moments of transition:

• Key Knowledge Is Trapped
  Trust structures, intentions behind decisions, advisor relationships, all critical, and often undocumented.
  
  
• Next Gen Feels Overwhelmed
  Successors are left to decode decades of decisions without context or guidance.
  
  
• Family Offices Rely Too Heavily on Memory
  Without a shared system, important details live in email threads, file drawers, or worse,  someone’s brain.
  
  

Josh puts it simply: “Pain is inevitable. Suffering is optional.” Families can’t avoid loss. But they can avoid the chaos that comes from poor planning.

The Solution: Centralized, Intentional Planning

leafplanner is a platform built to give families control over their complexity, and continuity across generations.

• Map the Full Picture
  Organize the people, structures, documents, and relationships that define a family enterprise.
  
  
• Enable Clear Succession
  Give heirs and advisors the clarity they need to step in with confidence.
  
  
• Preserve the Why Behind the What
  Because estate plans are only as good as the understanding that supports them.
  
  

Schedule a conversation and see how leafplanner can help your family build a lasting legacy, not just for today, but for the next generation and beyond.