In our experience working with thousands of retirees, we’ve noticed one common pattern:

People plan for their families, but rarely with them.

We’ve met close families who are open with each other… until money comes up.

No one wants to be the first to bring up the will or ask what happens if Mom gets sick.

But the truth is, almost every family shares the same root issue:

A misalignment of expectations.

Why It Happens

According to a recent Money Wise Institute study, 52% of adult children say they’ve never talked with their parents about basic financial planning, things like retirement goals, wills, or end-of-life wishes.

That silence has consequences.

As Gary Teelucksingh of the Money Wise Institute explains, “Eighty percent of parents say rising costs threaten their ability to leave an inheritance, while over half of millennials and Gen Z expect to receive an inheritance and one in four are actually counting on it as part of their financial plan.”

According to the Money Wise survey, 57% of Canadian parents now expect to spend most of their wealth during their lifetime, while 55% of Millennials and Gen Z still expect to receive an inheritance

Parents might feel uncomfortable discussing money, aging, or death.

Children might fear sounding entitled or triggering a defensive reaction.

But emotions like guilt, fear of burden, or loss of control can shut down the conversation before it even starts.

Imagine This Scenario

A husband and wife sit down to plan their legacy for their only son.

The husband wants to leave their son a specific amount and the wife agrees.

But by the next session, she’s had more time to reflect and now thinks: “What if we need more for later?”. With rising costs leading to an uncertain future, she believes they should set up an emergency fund, not because she doesn’t want to support her son, but because of what they can’t foresee happening.

The misalignment between the couple highlights a broader issue: if the parents aren’t on the same page, how can the family as a whole align?

It wasn’t a disagreement. It was just a conversation where priorities had changed.

At PKAG, we have a saying:

If the conversation is incomplete, your finances can’t compete.

How Can I Get My Family on the Same Page?

You don’t need to have everything figured out before you talk.

But you do need to start the conversation or at least be open to it if someone else brings it up.

Teelucksingh also said “The conversation isn’t about what I get or what I want. It’s about reverence. Families can start by asking, ‘How do we respect your legacy?’ That shifts the tone from awkward to meaningful.”

Here are a few practical ways to begin:

Start with your spouse
Retirement isn’t a solo plan. It’s a shared life phase.
You may have different dreams, but aligning on values, timing, and priorities is essential.

Hold a family meeting
Structure helps. Create an agenda with clear topics: retirement goals, inheritance expectations, caregiving roles, and legacy wishes.
Let everyone have a voice, but also define responsibilities.

Bring in a neutral third party
Sometimes it helps to have someone in the room who isn’t family.
Advisors, financial therapists, or mediators can keep conversations grounded in facts, not feelings.

Align siblings ahead of time
If you’re an adult child, get in sync with your siblings before meeting with your parents.
Presenting a unified message reduces confusion and prevents emotional flare-ups.

Document the essentials
Complete and update all wills, powers of attorney, health directives, and caregiving preferences.
It removes guesswork during already difficult moments.

As Teelucksingh notes, “The conversation isn’t about what I get or what I want - it’s about respect. Families can start by asking, ‘How do we honour your legacy?’ That changes the tone from awkward to reverent.”

Every family faces tough conversations around retirement.

The good news is, you don’t have to figure it all out alone - and you don’t have to get it perfect.

You just have to begin.

But don’t wait for a crisis to start the conversation.

At PKAG, we help families turn incomplete conversations into confident plans so you can move forward with clarity, trust, and alignment.

The earlier you talk, the easier it gets.

Estate planning should be a big part of your financial planning in retirement. Join us at our next in-person seminar where we talk about estate, finances and ways we can help you live the life you imagined in retirement:

Registering Here

Sources

https://www.edwardjones.ca/ca-en/market-news-insights/guidance-perspectives/family-meetings-empowering-platform-family-communication

https://www.moneywiseinstitute.com/press-1/brokenconversationsmay212025pressrelease

https://www.globenewswire.com/news-release/2025/04/08/3057503/0/en/Tariffs-Tension-and-the-Talk-that-s-not-happening-Half-of-Canadian-parents-haven-t-discussed-inheritance-plans-with-their-children.html