Tough Conversations

The tough conversations you should be having over the holidays this year.

Jacob Citron

11/16/20253 min read

clear glass chandelier turned on in room
clear glass chandelier turned on in room

With the holiday season fast approaching, Canadian millennials are getting prepared for their family gatherings. Having started families of their own, and with their parents firmly in their 60s and 70s, many millennials are starting to take over hosting duties. With the passing of the torch, it's the perfect time to have the conversation about aging and succession planning.

In other words, do you and your siblings know what is going to happen to your parents wealth and assets when they pass on?

For the majority of people, this is a really challenging conversation. Communicating across generations is difficult and any conversation about finances can be tense.

Nevertheless, it is vital that your family is on the same page about your parents' wishes for succession and their estate.

For example: Do you know what your parents want to do with their property and assets? Do they want to divide them amongst the kids equally? Do they want to pass the cottage down to one child and the family home to another? Do they want to give money to a charity close to their heart?

Do they want to split their assets equally? Pass it down to the kids or directly to the grandkids? What if you have three children and your brother doesn’t have any? Are you and your brother each getting 50% or are they giving you 75% to ensure that the grandchildren are taken care of?

What about the family business? If one daughter works for dad in the family business and the others don’t? Does that one daughter inherit the entire business? Or do they have to buy their siblings out? What if they have different ideas on how to run the shop? Who decides?

Or what happens if God forbid your parents become disabled or sick? Who do they want managing their affairs? Do you know what their wishes are around palliative care? MAID? Do they want to stay in their current house? Move into a seniors home? If so, do they know which one? Can they afford it?

Then what about caring for dependents, like a sibling with a disability, or grandma and grandpa?

Have they ever had a conversation about taxes and probate? In many scenarios, there could be a major tax liability at play. In other words, your family could owe hundreds of thousands of dollars to the government. If that is the case, how is the estate going to pay that money?

What about second families and step children? Valued friends or estranged relatives? Have they been considered?

It’s no wonder these conversations are often passed over or put on the back burner. They can make anyone’s head spin.

That’s why financial and legal professionals exist; To help you navigate these conversations with tact, respect, and grace.

It can be scary, but it is certainly necessary. The sooner you can break the ice and start communicating, the better. When life happens, you don’t want to be left scrambling to figure out finances while you’re focusing on caregiving or grieving.

If you feel like you’d like to have those difficult conversations but don't know how to go about it you can get the ball rolling and ask your parents: “Hey mom/dad, do you have a will?”. If they say yes, you can ask: “who is the executor of the will?”. If they say no, then you might want to ask them if it would make sense for them to start getting one drawn up.

Don’t feel confident in having the conversation? You can send them this article and see what they think about it.

Every family has its own unique dynamics and quirks - but every family needs some kind of plan.

At Citron Insurance, we specialize in succession planning, mitigating risk, and assessing and addressing tax liabilities. We also specialize in connecting our clients with the best lawyers, financial advisors, and accountants who work together to form your family’s advisory team.

These professionals exist to help people like you find solutions. So, get in touch, be brave, and remember with Citron Insurance, there is never any cost to consultations. We’re here to help.

Merry Christmas and Happy Holidays!

Have questions but don't know where to start?

Want to get notified when our next article drops?

Subscribe: