The first pass is documentary, not financial: locate the estate documents, confirm who holds powers of attorney, check that beneficiary designations still name the right people, and establish whether the drafted trusts were ever funded. Unfunded trusts and stale designations are common, and both override a will.
Adult children usually notice the problem before their parents raise it, and are the worst-placed people to bring it up. From a parent's side, a conversation about their finances can sound like an audit, a competence question, or a claim on the estate — sometimes all three at once.
What makes it possible is starting with paperwork rather than decisions. Confirming where documents are is practical, hard to hear as criticism, and happens to surface the items that matter most.
A sequence that tends to work
- 01Opening the conversation
Ask where things are, not how they are doing
"If something happened tomorrow, would I know where to find everything?" is a question about logistics. It is answerable without conceding anything, and it starts the conversation in a place that is genuinely useful.
- 02First review
Locate the documents and confirm who holds authority
Wills, trusts, powers of attorney for finances and for healthcare, and any advance directive. Confirm not only that they exist but who is named, since documents drafted decades ago frequently name people who have since died or moved out of the family's life.
- 03First review
Check beneficiary designations against the will
Retirement accounts, insurance policies, and transfer-on-death registrations pass by designation and override whatever the will says. Designations that were never updated after a death, a remarriage, or a birth are among the most common and most consequential things a decades-old arrangement leaves behind.
- 04First review
Establish whether the trusts were actually funded
A trust that was drafted but never had assets retitled into it does very little. This is a frequent finding and usually a straightforward fix, but only if somebody checks.
- 05After the documents
Then, and only then, look at the portfolio
A portfolio built for someone thirty years younger is worth discussing, but it is the second conversation. Plenty of these reviews conclude with the existing advisory relationship left in place and three specific items corrected. That is a good outcome, not a failed one.
- 06Ongoing
Connect it to the rest of the family plan
Care costs and gifting in this generation change what is available in the others. Reviewed in isolation, this produces a sensible plan for the parents that quietly conflicts with the one below it.
Common questions
How do I start a conversation with my parents about money?
Framing it as locating documents rather than reviewing decisions is generally easier for everyone. Asking whether you would know where to find things if something happened tomorrow is a logistics question, not a competence question, and it surfaces the highest-consequence items — powers of attorney, beneficiary designations, and whether trusts were funded.
What documents should aging parents have in place?
Typically a will, any trusts, a financial power of attorney, a healthcare power of attorney, and an advance directive. Equally important is confirming that the people named in them are still the intended ones, and that beneficiary designations on retirement accounts and insurance match — those pass outside the will and override it.
Can you review my parents' situation without them changing advisers?
Yes. Many of these reviews end with the existing relationship in place and specific items corrected. The firm acts as a fiduciary and is compensated by its clients rather than by moving accounts, so concluding that nothing should change is a legitimate result.
This guide is provided for educational purposes by Jason Howell Company. It is general information, not investment, tax, or legal advice, and it does not account for any individual circumstances. Decisions described here generally require a CPA, an attorney, or both.