May 20, 2025 | Planning Matters | 7 min read

Improving Communication & Decision Making in Family Enterprises

The Cordillera family had most of their plans on paper.

A successful second-generation manufacturing company, a diversified investment portfolio, a private foundation doing meaningful philanthropic work, and four adult children with varying degrees of interest in the family enterprise. From the outside, everything looked orderly and intact.

Beyond the surface, things weren’t moving. In fact, some family members weren’t even talking

The Cordillera family had not held a formal family meeting—ever. Decisions were made at the kitchen table, in passing conversations, or not at all. Alan and Marie, the second-generation leaders of the enterprise felt the growing weight of indecision regarding business direction, succession, and how - or whether - to involve the rising generation. Meanwhile, their adult children expressed uncertainty and sometimes resentment about what was expected of them.

The Cordillera family had a long-standing relationship with Doug, a highly respected and trustworthy wealth advisor. Doug helped them build financial strategies, manage risk, and plan their estate over decades. Through his intimate relationship as a trusted advisor, he noticed the growing stall in decision-making and increasing friction in the relationships. He understood it was time to collaborate with other trusted advisors to bring in different expertise to serve the family.

That’s when I was introduced to the family as a facilitator to enable the family to address the dynamics. The only gap in the planning was in the family system, as it often is for most families. My role was to help the Cordillera family have the conversations they weren’t having, and create the clarity, confidence, and connection they needed to move forward, together.

What followed was a journey that reshaped how the family defines wealth, makes decisions, and relates to one another. This article shares the results from our work together and suggestions for you to consider if you are in a similar situation. Whether you are navigating leadership succession, redefining your family’s definition of wealth, or engaging the next generation meaningfully, these actions can produce better outcomes and unity in your family.

A new definition of family wealth was introduced based on the work created and published by James E. Hughes, Jr., a sixth-generation counselor-at-Law, author, and expert in family generational wealth transfers. The Cordillera family embraced Hughes’ philosophy as a new way of thinking about family wealth on multiple levels:

• Spiritual: Share a common purpose where every member of the family by affinity seeks to enhance the other’s journey of happiness
• Social: Make effective joint decisions together
• Intellectual: Grow together as a life-long learning system and share what you learn
• Human: Ensure each family member is thriving
• Financial: Support the first 4 (above)
  
  

Developing Your Vision, Mission, and Values

To help my clients, I built and use a system I call Succession Frameworks^TM. Per the framework, my first step with the Cordilleras wasn’t tactical—it was deeply reflective and engaging. Following a discovery process, the family came together for a series of facilitated conversations designed to explore and answer some big questions and begin to create a new future.

Through personal exploration, development in communication skills, family conversations, and storytelling, they created a shared family vision, mission, and purpose:

Vision: We are a connected and evolving family rooted in learning, wisdom, and love.

Mission: We are creating an enduring foundation of communication engaged in building a multi-generational enterprise of great purpose and prosperity.

Purpose: Our family wealth is a tool to generate opportunities for improving lives – one person at a time, one family at a time, and one community at a time.

Understanding that values shape and colour decisions and actions, they whole-heartedly went through a process to articulate and define their family values:

• Communication: Sincere and honest dialogue conducted with open-mindedness
• Respect: Regard self and others with esteem and honour
• Integrity: Firm adherence to a code of doing the right thing while being accountable for the impact we have individually and collectively
• Leadership: Being a role model in self-directed growth and demonstrating care
• Resilience: The quality that allows us to deal with problems in a determined and effective way
• Commitment: A pledge and undertaking to service and contribution everywhere
• Balance: Refueling one’s soul through faith, love, work, rest, and play

Now the Cordillera family had the foundation in place to begin looking at decision-making.

The 3-Circle Model

Next they began learning about the widely accepted 3-Circle Model to understand the inherent complexities in family enterprise.

They now recognized their decision-making style was informal and reactive resulting in growing family friction. Historically, they gathered input from whoever was in the room, defaulted to directive decision-making, and often deferred tough calls. It had worked—more or less—until the complexity, uncertainty about the future, and generational diversity of the family increased.

The family identified the different kinds of decisions in each system and determined whether consensus is required, as well as distinguished having a vote from having a voice on issues. This collaboration increased family unity, understanding, and cleared the pathway to design a structure to make decisions that align with, and extended from the framework.

From this work, we co-created a family decision map. Operational decisions about the company remained with the shareholders, family both working in the enterprises and those who were not, and non-family executives. Long-term strategic decisions, such as whether to sell or acquire, were addressed in both the family and ownership systems. This allowed a voice for those in the family system who accepted they did not have a vote in the final decision.

The Cordillera family revisited a thorny issue: whether to sell a non-core division of their business. Previously, the conversation had been emotional and unfocused. The framework and decision map became the compass for the family to list possible paths forward and evaluate them based on criteria rooted in their vision and values. For example:

• Financial implications were balanced and aligned with vision and purpose.
• Legacy and reputation now had a shared definition informed by their values.
• Impact on employees included considerations for stewardship and service.

The family connected through a shared framework that honoured both data and meaning. Establishing a process doesn't eliminate disagreement. It does build trust and grow understanding, making it easier to live with decisions and outcomes—even if a person doesn’t have a vote.

Most importantly, the Cordillera family were now making decisions instead of being stalled and bogged down in circular conversations.

Closing Reflections

By the time we wrapped up our initial engagement, the Cordillera family had:

• Articulated a family vision, mission, purpose, and shared values
• Successfully navigated the sale of their non-core division
• Created Succession Frameworks^TM as the foundation for transparent decision-making
• Engaged the rising generation to participate meaningfully and strengthened communication to move forward—together

They results went beyond making better decisions. They were unified because they were grounded in who they are and where they’re going.

For Your Family

If you're unsure how to start, you are not alone. Many families don’t know where or how to begin. Taking a step, like the Cordillera family can open new pathways to clarity and connection. As you reflect on your own journey, here are some suggestions to use the 3-Circle Model and a decision map and a few questions to spark meaningful dialogue:

Increase Clarity and Understanding

• Use the 3-Circle Model to identify:
  • The family members and stakeholders in the 3 systems
  • Strengths in each system to leverage
  • Challenges and/or issues in each system
• Decision Map:
  • Use the example of the map to design one that fits your circumstances and purpose
  • Name the decisions that must be made in each system
    

Vision, Mission, Purpose, and Values

• Who are we committed to becoming as a family?
• What is our vision individually and collectively?
• What are our aspirations and higher purpose for our family and wealth?
• What impact are we committed to having on each other, our businesses, and the world?
• What are our values, individually and collectively?
  

Decision-Making

• How do we currently make decisions?
  • Is our process clear, inclusive, and transparent?
• What criteria guides our most important decisions?
  • Are we aligned on what matters most to us?
• What are the types of decisions and who has authority to make final decisions on different matters (ownership, business, philanthropy, etc.)?
• What level of consensus or majority is needed to move forward?
• Are we making the most of our advisory relationships?
  • Do we have someone who can help us with the human side of wealth, business, and legacy?
    
    

The Role of Trusted Advisors

Traditionally, business owners and families have relied on advisors primarily for financial, legal, insurance, and tax-related strategies. While essential, both clients and advisors must realize navigating complexity goes beyond the numbers. The planning must be integrated, placing the humans at the centre accounting for and addressing the narratives, relationships, and communication. After all, in the end, everything is for family!

This is where a broader view of a trusted advisor is essential. The wealth advisor who introduced me to the Cordillera family deepened loyalty and trust in every possible way.

Family advisory planning and support doesn’t replace financial or legal team—it secures and complements it. Think of it as adding a layer of relational intelligence and systems thinking to the process. Recognizing and serving the family holistically is the future of family wealth advising.

About the Contributor

Trudy Pelletier is the founder and president of the Family Stewardship Group. Trudy has been serving family enterprise clients for 16 of 19 years in business, specializing in family communication and governance for succession and continuity planning. She is a Family Enterprise Advisor (FEA), Certified Exit Planning Advisor (CEPA), Certified Executive Coach (CEC), and mediator. Trudy’s personal mission is to liberate and unify families in love and purpose. Her vision is a world in which each person lives their potential realized. She can be reached at trudy@familystewardshipgroup.com.