What are “tricky conversations” in the world of trusts?

“When the winds of change blow, some build walls while others build windmills.”

In the context of wealth and succession, change is inevitable. And while it offers opportunities for growth and connection, it also introduces tension, uncertainty and risk, especially for families with complex structures, multiple stakeholders and deeply rooted emotional histories.

Families rarely begin with conflict in mind. Whether driven by hope, legacy or love, settlors often start from a place of intention: to build something enduring and joyful. But in high-net-worth families, particularly where wealth is intergenerational and held in trust, the dream can become fragile. Disappointment, miscommunication or perceived injustice can create deep wounds, often years after the original intentions were set.

These are the moments when tricky conversations become necessary. And yet, these are the very conversations families, trustees and advisers are often least equipped to manage.

The psychology behind conflict in family wealth structures

Why do certain conversations go so wrong, even when everyone seems to want a resolution?

It helps to understand how the brain works under threat. When individuals feel emotionally unsafe, triggered by perceived injustice, exclusion or conflict, the amygdala and brainstem activate our “fight, flight, freeze” response. We become reactive, defensive and less able to engage in reflective or reasoned thought.

In contrast, our “wise mind”, located in the cortex, is where reasoning, empathy, imagination and language live. It is the part of the brain we need when navigating emotionally charged topics.

In the world of trusts, clients (and sometimes trustees) are often already operating with a threat dial set high. A contentious family meeting, a change in distribution policy or the death of a patriarch can push individuals into high-alert mode, where reasoning gives way to blame, anger or withdrawal.

If we try to engage someone in this state with logic or governance structures, we are unlikely to reach a constructive outcome. What is required is a strategy for bringing people back into their wise mind before meaningful dialogue can begin.

When conversations do not happen, or when we avoid raising difficult topics, something else occurs: we begin to imagine.

Avoidance is not just a behaviour; it is a defence against shame, disappointment or fear. Instead of confronting a difficult issue, we create what I call imagination ships - narratives constructed in the absence of facts, often based on assumptions about others’ intentions or feelings.

These imagined stories become emotionally charged: “She does not respect me.” “They have always favoured his side of the family.” “They are plotting to push me out.”

The danger of imagination ships is that they escalate conflict without engagement. They turn small misunderstandings into entrenched beliefs, leading to isolation and, in some cases, litigation.

Understanding that behind blame is often hurt or despair allows us to change course. As Seidenfaden et al. (2011) suggest, we can transform power struggles into opportunities for connection, if we are willing to acknowledge the pain beneath the anger.

Imagination, curiosity and the power of “not knowing”

In wealth advisory and fiduciary roles, there is often pressure to be the expert, to have answers and authority. But some of the most powerful conflict-resolution work begins with acknowledging what we do not know. Sitting with uncertainty, and approaching families from a stance of curiosity rather than instruction, allows for a deeper connection and a greater chance of understanding the real issue beneath the surface.

Risk-taking and trust, relationship building

There is a common belief that the longer a relationship has lasted, the more risks it can bear. But in my experience, trust often grows from the courage to have difficult conversations early on. Showing vulnerability, expressing uncertainty or asking permission to explore sensitive ground can build trust, not diminish it.