Recently, I joined Peita Diamantidis on Ensombl’s Intergenerational Conversations series to discuss a topic that has become increasingly central to the work we do at Stephan Independent Advisory.
The conversation explored how advisers can help families navigate wealth, succession, relationships and change across generations. While we covered everything from family dynamics to how advisers can use AI to make space for more meaningful client relationships, one particular comment from Peita stayed with me.
“It’s not intergenerational wealth,” she said. “It’s intergenerational chaos.”
It was a light-hearted remark, but there is a great deal of truth in it.
When people think about intergenerational planning, they often think about wills, trusts, estate plans and tax strategies. Those things are important. Yet in my experience, they are rarely the most difficult part.
The real challenge is that families are complicated.
Families Are Ecosystems
When we think about a client, it’s tempting to focus on the person or people sitting directly in front of us – a couple, a business owner, or a retiree.
But families are ecosystems, which means no one exists in isolation.
Every family member influences the wider system. Decisions made by one person often have consequences for others, whether those impacts are immediate or only become apparent years later.
A parent helping an adult child into the property market may affect their own retirement plans. An ageing parent requiring care can influence where a family lives, how they work and the decisions they make about their future. A family business may create opportunities for one generation while creating expectations for the next.
Just as changes within a natural ecosystem can affect the health of the whole environment, changes within a family often create ripple effects throughout the broader family system.
This is why some of the most important conversations in financial planning have very little to do with financial products – instead, they’re conversations about priorities, responsibilities, values and relationships.
Understanding What’s Really On Their Mind
One of the observations I’ve made throughout my career is that even the most well-considered strategies can sometimes fail to gain traction.
Not because the strategy is wrong or the client doesn’t understand it, but because something else is weighing on their mind.
This is one of the reasons why, at Stephan Independent Advisory, we spend so much time asking questions that extend beyond finances.
Who do you feel responsible for?
What does helping your children actually mean to you?
How prepared are you if something changes for your parents?
What does legacy mean?
The answers often reveal far more than a balance sheet ever could – and help direct our strategy moving forward.
The Importance of Time, Effort and Trust
One of the challenges with family-centred advice is that meaningful conversations can’t be rushed.
Trust takes time to build.
People rarely reveal their deepest concerns in the first meeting. In fact, in many cases, clients are still working through those concerns themselves.
A husband might admit a long-held dream that his partner has never heard before. Parents may realise they have made assumptions about what their children want. Family members may discover they have very different views about inheritance, support or responsibility.
This is why we keep the number of clients we work manageable and at a number that reflects the depth of understanding we seek to have. It allows us to spend time understanding not just the financial position of a family, but the broader context surrounding it.
Preparing People, Not Just Assets
Much of the discussion around intergenerational wealth focuses on transferring assets.
Yet successful transitions are often less about the assets themselves and more about the people receiving them.
Are future decision-makers prepared? Do family members understand the intentions behind key decisions? Have expectations been discussed openly? Have important conversations been delayed because they’re uncomfortable?
In many cases, helping a family prepare for the future involves education, guidance and communication as much as it involves financial planning.
A Personal Perspective
My own interest in intergenerational planning stems partly from experience.
When my father passed away, our family was suddenly navigating grief, estate administration and a host of important decisions all at once. As the eldest son, I found myself trying to support my mother, bring my brothers together and make sense of something I wasn’t fully prepared for.
What stayed with me was the feeling of responsibility.
Who was there to help us navigate the process? How did we know which professionals to trust? What conversations should we have been having?
Looking back, that experience shaped how I think about advice.
The longer I work with families, the more convinced I become that intergenerational planning isn’t really about transferring wealth from one generation to the next.
It’s about helping families prepare for change, navigate uncertainty and preserve relationships, values and opportunities alongside wealth.
Intergenerational planning is a complex area, and my chat with Peita Diamantidis covered many more ideas than I could capture in this article. If you’d like to explore these themes further, I encourage you to watch the full conversation here.
