Complex families require collaborative advisory: Why we work in teams at Generation6

Advisory teams often outperform individual consultants,
because complex families require more than a single point of view. 

At Generation6, we rarely work alone, and that is very intentional.

The multigenerational enterprising families we serve operate at the intersection of family, ownership, governance, business, and wealth. These systems are emotionally charged, historically layered, and strategically complex. Rarely can one single advisor, no matter how experienced, fully grasp and address all of these dimensions alone, while simultaneously dealing with often large shareholder groups with diverse perspectives.

Working in teams is not just our preferred way of working. It is a quality standard.

Below is why we think team-based advisory work leads to better outcomes for the families we serve, and why research and practice strongly support this approach.

1. Complex Systems Require Multiple Lenses

Family enterprises are classic complex adaptive systems. Decisions in one domain (e.g., governance) inevitably ripple into others (e.g., family dynamics, ownership expectations, leadership succession).

Research in professional services consistently shows that diverse expertise improves diagnostic accuracy and reduces blind spots—particularly in ambiguous, high-stakes contexts. Team-based advisory models allow for:

• Strategic and relational issues to be addressed simultaneously

• Economic logic to be balanced with emotional realities

• Short-term decisions to be evaluated through a long-term, generational lens

At Generation6, this means combining perspectives from governance, family dynamics, education, finance, and organizational development; not sequentially, but integrative.

2. Better Judgment, Fewer Biases

Even the most seasoned advisors are subject to cognitive bias. Team-based work introduces what the literature calls “constructive dissent”—the ability to challenge assumptions before they become recommendations. Teams have been shown to make more robust decisions in uncertain environments, be less prone to overconfidence and confirmation bias by way of continuous feedback and structured reflection, and provide redundancy of understanding, reducing the risk of misinterpretation. For families, this translates into advice that is tested, debated, and refined.

An additional safeguard in this process is Generation6’s orientation check approach, which provides a level of quality control that is difficult to achieve in purely individual advisory work. Every case is regularly reviewed with a designated expert “orientor” who is not embedded in the day-to-day execution, but whose role is to challenge framing, surface blind spots, and add seasoned perspective.

This structured second look ensures that emerging conclusions are tested early, assumptions are made explicit, and alternative interpretations are considered before advice is finalized. In practice, the orientation check reinforces disciplined judgment and materially reduces the risk that individual bias, momentum, or familiarity with a family system goes unexamined

3. One Family, Many Relationships

Advisory work with families is deeply relational. Trust does not only form between a family and an individual advisor, but between the family and the advisory system supporting them.

This matters particularly because multigenerational families are not monolithic. A founder, a next-generation sibling group, an in-law, and an independent board chair often experience the same situation very differently. Teams allow us to match advisor style and expertise to different stakeholders and offer multiple relational touchpoints across generations, roles, and personalities

4. We Orchestrate with Existing Advisors

Enterprising families rarely start with a blank slate. By the time they engage us, they are often already supported by a trusted network of legal, tax, investment, accounting, and fiduciary advisors, many of whom have long-standing relationships with the family.

At Generation6, we see this not as a complication, but as a critical asset. Our role is not to duplicate expertise or compete for territory. It is to connect the dots, to ensure that governance structures, family processes, educational initiatives, and ownership decisions are coherent with what is already in place legally, fiscally, and structurally. Our teams complement technical experts and support advisors by clarifying the “why” behind family decisions, not just the “what”.

Because one of the most common risks in complex family systems is not poor advice, but misaligned advice:

• A governance solution that unintentionally conflicts with trust structures

• A family policy that creates tax or liquidity challenges

• An ownership framework that is elegant on paper but impractical within existing legal constraints

Service industry research and applied advisory literature consistently show that coordination failures, rather than technical errors, are the primary source of dissatisfaction in professional services. Families suffer when advice is optimized in silos.

Because we are not selling legal structures, financial products, or investment solutions, we can act as a neutral convener among advisors. This often includes:

• Facilitating structured conversations between family members and external advisors

• Translating family intentions into language that legal and tax professionals can work with

• Stress-testing proposed solutions across disciplines before implementation

For families, this reduces friction, accelerates decision-making, and minimizes the risk of costly rework later.

5. We Practice What We Preach

At Generation6, we frequently encourage families to:

• Build effective boards

• Invest in governance structures

• Create shared leadership models

Working in teams is our way of living these principles ourselves. It reflects how we believe complex ownership systems should be stewarded: collaboratively, intentionally, and with humility.

What This Means for Our Client Families

When you work with Generation6, you are not hiring a single expert. You are engaging a coordinated advisory team that:

• Thinks systemically

• Challenges itself before challenging you

• Brings depth without dogma

• Holds your family’s long-term continuity at the center of every decision

In short: we work in teams because your family enterprise deserves more than one voice, but one aligned direction.

If you’d like to learn more about how our team-based approach supports governance design, family development, education, or family office work, we’d be glad to continue the conversation.