Family Crossroads
A 2-day decision-making workshop
Taking wise action as a family
Navigating major decisions as a high net worth family can be complex and emotionally charged. Whether you’re considering a business transition, legacy planning, or another significant family concern, the choices you make impact your family for generations.
This exclusive 2-day intensive provides your family with a structured process to engage in a frank and empathetic dialogue, discern options, and commit to a path forward with clarity and confidence.
Together you will discern what “wise action” means at this moment in your family’s journey.
- Clarity and confidence to move forward with your decision
- Resolution of conflicts that block forward progress
- Deeper understanding of each family member’s core needs and concerns
- Improved skills for mutual support and communication
Day 1
Develop a Clear, Honest, &
Comprehensive Vision
- Anchor in your family’s values, promises, and aspirations
- Establish norms for self-care, support, and healthy boundaries
- Engage in caring dialogue to invite all perspectives
- Develop a shared vision of an ideal outcome
- Identify blocks to forward movement
Day 2
Take Responsibility for
Loving, Wise Action
- Generate scenarios that account for the blocks
- Discern using multiple lenses: cognitive, emotional, somatic, intuitive, and practical
- Identify a path that supports holistic family wellbeing
- Develop a preliminary action plan
- Identify key stakeholders whose engagement is needed for you to succeed
Sample family decision-points
Wealth Transfer and Legacy Planning
- Addressing concerns about the impact of wealth on the next generation’s work ethic.
- Determining the best way to educate and prepare heirs for their future responsibilities.
- Whether and how to include an estranged family member in an estate plan.
- Determining the appropriate level of financial support for adult children.
- Deciding on the appropriate level of involvement in political or social causes.
Family Dynamics and Relationships
- How to begin reconciling with an estranged family member.
- How to create boundaries with an overzealous friend or acquaintance.
- How to engage with a beloved ex-spouse after divorce.
- Whether to intervene in a hurting marriage within the family.
- Navigating the complexities of blended family dynamics after remarriage.
- How to handle disagreements over the distribution of inheritance or assets.
Relationships and Wealth Management
- Whether to invest in a friend’s or family member’s business venture.
- How to share or whether to sell a family asset (i.e., “the family cabin”).
- Whether to sell a family asset (i.e., “the family cabin”).
- Whether to establish a family foundation or donor-advised fund.
- Determining clear roles and boundaries with the family office in day-to-day affairs.
Philanthropy & Community Involvement
- Whether to invite spouses/partners to participate in family philanthropy.
- Choosing priorities for philanthropic giving.
- Creating guidelines for family vs. staff roles in community life.
- How to handle requests for financial assistance from extended family members.
- Deciding on the appropriate level of involvement in political or social causes.
Personal and Lifestyle Decisions
- Choosing how to prioritize time after retirement.
- Deciding whether to relocate.
- Clarifying how to say “no” without harming a valued relationship.
- How to balance privacy concerns with the desire for transparency within the family.
- How best to support a family member who has fallen on hard times.
