Avoiding the conversation could cost far more than just money
There’s a conversation missing in most families. Not because it isn’t important, but because it feels too awkward to start. It’s the conversation between adult children and their parents about money. Not about inheritance or handouts but about understanding where things stand. The truth is that financial silence is rarely harmless. And as parents age, that silence often turns into confusion, missed opportunities, and irreversible mistakes.
Lately, I’ve been asked by a number of people how to approach these conversations. In almost every case, it starts with a quiet concern. A parent mentions a policy they’re unsure about, or an investment they haven’t reviewed in years. And when someone finally looks under the hood, things are often more complicated—and more fragile—than anyone realised.
We don’t talk enough about money. Especially not with our parents. And yet, one of the most important financial conversations you may ever have won’t be with your adviser, banker, or accountant. It will be with your mom or dad.
For many of us, the idea of sitting down with our parents to talk about their financial affairs feels uncomfortable—maybe even inappropriate. That’s largely because our parents grew up in a world where financial matters were deeply private. You didn’t talk about money around the dinner table. You didn’t ask your friends about their investments. You didn’t challenge the bank manager. And you certainly didn’t share financial worries with your children.
But that culture of secrecy has come at a cost. Too many of our parents have had to navigate complex financial decisions alone—often without context, second opinions, or a plan. And as we’ve seen time and again, a poor decision left unchecked doesn’t just sit quietly. It compounds. Over time, this can lead to inefficient estate plans, misaligned portfolios, lapsed policies, or unnecessary financial stress that could have been avoided with one honest conversation.
It doesn’t have to be this way.
Why These Conversations Matter
It’s not about control. It’s about clarity, and sometimes, correction. A single conversation could help:
- Identify overlooked opportunities: Your parents might be sitting on an outdated will, a misaligned trust, or tax inefficiencies they’re unaware of.
- Prevent irreversible mistakes: Many estate planning issues become far harder to fix when health declines or mental capacity is impaired.
- Reduce family conflict: Siblings and spouses often only discover what’s “in the plan” after a death or health crisis, when it’s too late to ask questions or offer input.
- Ensure dignity and independence: With the right planning, your parents can stay in control of their choices and future, not be dictated by financial limitations or administrative confusion.
How to Start the Conversation (Without Creating Conflict)
This isn’t a one-size-fits-all exercise. Some families are open, others more private. But here are some approaches that work:
- Use your own planning as a door opener
“I’ve been working on updating my financial plan, and it made me realise how important it is to know where things stand. Have you reviewed yours recently?”
- Frame it as a legacy conversation
“It’s important to me that we honour your wishes when the time comes. Can we talk through how you’ve structured things?” - Ask about lessons
“What were some of the biggest money decisions you made? Anything you wish you’d done differently?” - Involve a trusted third party
Sometimes an objective voice, such as a wealth manager, accountant, or attorney, can help navigate the tough topics and mediate where needed.
Topics to Cover (Gradually)
No need to make this a one-hour interrogation. Let it evolve. But over time, make sure you discuss:
- Estate documents: Wills, powers of attorney, and whether they’re up to date
- Income planning: Are their current investments appropriate for their stage of life?
- Insurance coverage: Life, medical aid, long-term care. What’s in place and what’s not?
- Digital estate: Passwords, subscriptions, and online accounts that need to be tracked
- Family roles: Who’s the executor? Who has signing rights if something happens?
Don’t Wait for a Crisis
Too often, families only have this conversation when it’s already too late. After a stroke, a diagnosis, or a sudden death. That’s when the damage is hardest to undo and the emotions are highest.
Talking early allows for better planning, calmer thinking, and more options. And when done with empathy and respect, it can actually bring families closer, not push them apart.
This is not about invading your parents’ privacy or questioning their competence. It’s about helping them maintain their independence, dignity, and financial wellbeing for as long as possible.
And it may be the most loving act of planning you ever do.
