When experts fail, and instincts are set aside

Konstantin Levin walked the fields of his family estate, boots heavy with soil, as his mind churned with unease. The manager he had hired, armed with advice from modern agricultural experts, had promised efficiency and higher yields. At first, Levin deferred to their authority, nodding silently as they implemented unfamiliar methods across the estate. Yet, deep down, he felt a growing disconnection between their plans and the land he knew so intimately.

Levin’s story is one of the central threads in Tolstoy’s Anna Karenina. A landowner deeply tied to the rhythms of his estate, Levin seeks to improve it by adopting contemporary techniques. Encouraged by confident experts, he steps back, allowing their methods to take root. But as time passes, Levin begins to notice that something is wrong. The land shows signs of strain, the peasants grow frustrated, and the harmony of the estate begins to falter.

Eventually, Levin takes matters into his own hands. He walks the fields himself, speaks with the peasants, and observes the effects of the changes firsthand. Slowly, he comes to understand the disconnect: the expert advice, though rational on paper, was ill-suited to the specific realities of his estate. Reflecting on his experience, Tolstoy writes of Levin, “He came to the conclusion that he must trust not what others said, but his own observations.”

 

The challenges of “invisible fields”

Levin’s experience highlights a timeless challenge—how expertise often overlooks the realities of those it serves. In his case, the fields were right before him. He could walk them, engage with the peasants, and uncover the disconnect himself.

In today’s world, however, we face challenges of a different magnitude. When dealing with cross-border regulations, complex financial instruments, intricate family governance structures, or even cybersecurity, the fields we must navigate are often invisible to us, shrouded in technical jargon and expertise that we may not fully understand.

The enigma, then, is this: How can we ensure that the advice we receive serves our true needs, rather than being dictated by the biases of the advisors we rely on? How can we “observe” and assess the advice we’re given when the terrain is unfamiliar, the stakes are high, and the tools to evaluate it lie outside our expertise?

 

The issue of advisor bias

Imagine a family newly transitioning from operating a business to managing generational financial wealth. They meet with advisors who come highly recommended—lawyers, financial planners, and investment managers. Each advisor presents their own plan: tax-efficient trust structures, diversified investment portfolios, governance mechanisms to ensure smooth decision-making. Individually, the recommendations sound polished and logical.

But beneath this polished exterior lies a question the family may not even think to ask: Whose priorities are these solutions serving? A tax advisor may prioritize minimizing liabilities, even if it adds complexity. An investment manager may favor strategies aimed at maximizing returns, even if they expose the family to higher levels of risk—or align with fee structures that reward frequent trading or complex financial products. A governance expert might over-engineer decision-making processes to meet theoretical ideals, overlooking the family’s unique dynamics.

None of these perspectives are inherently wrong. But they reflect the advisors’ biases: their focus on solving the part of the problem they know best, rather than seeing the whole.

What makes advisor bias particularly insidious is that it often goes unquestioned. The authority of expertise—bolstered by confident presentations, data-driven arguments, and technical jargon—can leave families hesitant to push back. Much like Levin, who initially deferred to his estate manager’s modern methods, families may feel they lack the knowledge to challenge what is being presented.

This dynamic is further compounded by the complexity of the matters at hand. Cross-border regulations are an ever-shifting labyrinth, making it difficult to distinguish essential safeguards from unnecessary complications. Cybersecurity, while crucial, can be overstated to the point of fear-mongering. Financial investments often come wrapped in layers of strategies and products that obscure their true cost or risk.

Governance structures, too, are not immune to this challenge. Meticulous frameworks—carefully crafted family values, mission statements, and detailed dispute resolution clauses—may look impressive on paper but often remain unimplemented. Without a genuine connection to the specific family, its unique dynamics, and real-life circumstances, these structures risk becoming theoretical exercises rather than practical tools that guide future generations.

 

Breaking through the bias

Levin’s lesson—trust your own observations—remains vital. In today’s world, this doesn’t mean rejecting expertise but rather finding ways to maintain agency and navigate advice critically. While we may not always be able to “walk the fields,” families can take steps to ensure the advice they receive serves their true needs.

The first step is recognizing that bias exists. Advisors, no matter how skilled, view problems through their own professional lens. A tax lawyer may instinctively prioritize compliance and savings over simplicity, while a financial advisor might emphasize growth strategies that align with their firm’s products. Acknowledging these perspectives is not about suspicion—it’s about thoughtful engagement: What assumptions underlie this advice? Whose priorities does it serve?

Equally important is ensuring that advisors understand the family’s unique context. Cookie-cutter solutions often falter when applied to nuanced realities. A family with deep entrepreneurial roots, for example, may find a rigid trust structure stifling, even if it minimizes taxes. Families can take proactive steps to improve the quality of advice they receive—not by outsourcing critical conversations to technical experts who may lack the broader perspective but by engaging meaningfully, offering insights into their business, dynamics, and long-term objectives. Ultimately, ensuring relevant and effective advice is not solely the advisor’s responsibility—it requires the wealth owner’s willingness to articulate their vision and strategic goals.

To prevent decisions from being shaped by a single discipline, families should encourage collaboration among professionals with varied expertise—legal, financial, tax, and governance—so that different perspectives challenge assumptions. A trusted individual—such as a longtime business associate, independent board member, or senior family office executive—can further help bridge technical expertise with real-life family dynamics, ensuring that structures align with governance needs rather than becoming rigid formalities. A strategic wealth planning advisor can also act as a coordinator, integrating expertise across disciplines and ensuring advisors do not operate in silos. These steps help balance diverse viewpoints and create a more cohesive, well-aligned wealth strategy.

At the same time, families must empower themselves to ask questions. While complex matters like cross-border tax structures or cybersecurity may seem intimidating, they should insist on clear, jargon-free explanations and engage actively in decision-making. Even simple questions—Why is this approach better than the alternatives? What will this cost in time, effort, or flexibility?—can reveal whether the advice truly aligns with the family’s goals. Seeking second opinions can provide further clarity, ensuring that decisions are well-balanced rather than shaped by the strongest voice in the room.

This process becomes particularly crucial during generational transitions. Advisors who have worked with the family for decades may possess valuable institutional knowledge, but they also risk being locked into established patterns—“rails” that may no longer fit as the family evolves. Younger family members, or those who marry into the family, often feel intimidated or even patronized by long-standing advisors, particularly in sensitive moments like succession.

Yet, the younger generation also brings fresh perspectives. Often well-educated and globally informed, they may ask questions or challenge assumptions that their parents or elders did not. When embraced constructively, this interplay of experience and curiosity can enrich decision-making. By encouraging younger members to engage while ensuring they feel respected and heard, families can foster a collaborative environment where insights from all sides—advisors, elders, and successors—lead to more balanced and forward-looking outcomes.

These strategies are not about rejecting professional advice but about ensuring it becomes a tool for empowerment rather than a source of dependency. Levin’s story reminds us that even the most polished solutions can falter without alignment to the realities of those they are meant to serve. By fostering critical engagement, cross-disciplinary collaboration, and measured adaptation, families can build systems that balance trust with agency—creating outcomes that reflect both expertise and their own values.

 

From blind trust to thoughtful stewardship

Advisor bias is not a failing of individual advisors but a reflection of human nature. Expertise, no matter how polished, can miss the mark when disconnected from the unique context of those it is meant to serve. As Levin discovered, success lies not in rejecting advisors but in approaching them critically—with both trust and discernment.

In today’s complex world, where the fields we must navigate are abstract and specialized, families must build systems that encourage engagement and accountability. This means fostering a culture where questions are welcomed, advisors collaborate rather than dictate, and decisions align with the family’s reality and long-term vision.

Ultimately, the responsibility for decisions must remain with the family. While advisors can provide expertise and guidance, stewardship requires that families define their own values and goals, ensuring these drive the process. By retaining this ownership, families safeguard their legacy, adapting to the complexities of modern wealth and governance without losing sight of their unique identity.

Levin’s story in Anna Karenina reminds us that thoughtful leadership is essential when navigating uncertain terrain. Families that thrive across generations combine the insights of advisors with their own critical engagement. By asking the right questions, involving diverse voices, and ensuring that advice reflects their values, they transform from passive recipients of advice into confident stewards of their legacy, shaping their future with clarity and intent.

 

Reflective questions: navigating advice and reclaiming agency

 

Understanding advice

1. What assumptions underlie the advice I am receiving?
2. Beyond my own, whose priorities might this solution serve?
3. Am I receiving clear, jargon-free explanations, or do I feel overwhelmed by technical complexity?
4. How well does this advice align with my family’s unique circumstances and long-term goals?

Evaluating advisor bias

1. Are my advisors taking the time to fully understand my family’s values, goals, and dynamics?
2. Do I feel comfortable challenging my advisors, or does their expertise intimidate me?
3. Have I sought diverse perspectives to uncover potential blind spots in the advice I’ve received?
4. What steps can I take to encourage cross-disciplinary collaboration among advisors for more well-rounded decision-making?

Empowering the family

1. Is our family actively engaged in decision-making, or do we defer too much to external advisors?
2. How are we integrating the younger generation into these discussions? Are their perspectives valued?
3. How can we test strategies on a smaller scale to minimize risks before making larger commitments?