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How To Talk To Your Loved Ones About Your Will

February 18, 2021
Mallory McGrath of Viive Planning shares some dos and don'ts when it comes to discussing your Will with loved ones
Written By Mallory McGrathFebruary 18, 2021

I am often asked by my clients for suggestions and advice on how to talk to their loved ones about the contents of their Will. It’s not an easy answer, and sometimes I wish it was. Families are complex, and every family behaves differently as a unit and as individuals.

However, no matter if you are a part of a nuclear family, blended family, single-parent family, you are single/married with no children, or any other combination of a family-unit, here are some do’s and don’ts that I’ve found helpful for the families I’ve worked with at Viive Planning.

Don’t assume

Remember the saying, “If you assume, you make an a** out of you and me.” I try to keep this in mind whenever I’m working with clients to prepare for a Collaborative Meeting with their closest family members.

Don’t assume that your daughter is going to try to control the situation.

Don’t assume that your brother will bail on the meeting because he thinks that pre-planning is a waste of time.

Don’t assume that your children all love and respect each other and always will.

Don’t assume that you won’t get the love and support that you deserve.

Don’t assume that you won’t have the strength to share your wishes and desires with those you love and hold dear.

A Collaborative Meeting with your family and loved ones is an opportunity for you to share with them and for them to listen. If you choose not to welcome their input, then make sure they know that upfront. If you do choose to welcome their input, then be prepared for it. And by “be prepared,” I mean do not make assumptions about what they may or may not say.

And by “be prepared,” I mean do not make assumptions about what they may or may not say.
Mallory McGrath

For example, let’s say you just told your son and daughter that only your son would be the executor of your Will. After making this announcement, try saying something like, “If either of you has any thoughts or feelings about this choice that I’ve made, I would appreciate hearing them. I am open to explaining my choice to you if you would like an explanation.”

Show your children upfront that you are an open book and want them to understand your wishes and desires. Being receptive to their feedback does not mean you are going to change your mind, but you are open to sharing your thoughts behind your choices and hearing how it makes them feel.

Don’t berate

Most people start discussing aging and end-of-life after they’ve hit that 65-year-old mark. If you have children and are over 65 years old, chances are those children are full-grown, independent adults. You are now at a point of time in your life where you and your children are equals in some sense. You both earn money, you both may have families, successful careers, etc.

Try to remember what it was like for you when your aging parents still “parented” and lectured you. Your adult children do not want to be berated and told what to do. They want to be a part of the conversation and have their own thoughts and views respected.

In the end, it’s your life and your choice, but if you choose to include them in a Collaborative Meeting, then you need to treat them with the respect that any adult deserves.

Try starting your sentences off with:

  • I appreciate your response…
  • I appreciate your views on my choices…
  • Thank you for sharing your feelings…

You can also ask questions like:

  • How does this choice make you feel?
  • Do you understand my reasoning behind these choices?
  • Is everyone comfortable with what I’ve said so far?

Do share

I hate to be the person who quotes a big, purple dinosaur (yes, I’m talking about Barney), but sharing is caring. It really is. Sharing how you feel and what you want out of life shows how much you care about the person you are sharing it with. It shows your trust, respect, and acknowledgment for that person.

I’m not saying it will be easy; in fact, it’ll be downright hard. Talking about aging and end-of-life can be very difficult to do… the first time around, that is.


Talking about aging and end-of-life can be very difficult to do… the first time around, that is.

After that first time, it becomes simpler and easier with each time you have the discussion. The people with whom you choose to keep sharing your future plans will feel loved and accepted by you. These conversations are meant to unify families, not tear them apart.

Do recognize

Recognize how your children and loved ones are similar to you and also how they are different. Recognize that each person who you share these personal details with will have different views and opinions.

Recognize that you appointing someone as your executor or Power of Attorney means you are giving them a job to do on top of their every-day life and work.

Recognize that, as hard as it is for you to talk to your children about your inevitable death, it is equally hard for them to hear you talk about it.

Recognize that as a parent, you have a responsibility to teach your children about planning for their future and that discussing life, death, and money is not a taboo dinner-table topic.

I don’t deny that having these conversations are difficult. Most people assume that I can have these conversations with ease with my own family; that could not be further from the truth.

Discussing the aging process and one’s end-of-life wishes is challenging, but the long-term rewards greatly outweigh that discomfort in the short term.

The long-term rewards [of having these conversations] greatly outweigh that discomfort in the short term.

If you find that you don’t know how to start the conversation or find that your loved one won’t let you discuss it with them, don’t fret. There are more opportunities and different ways to approach each person, like working with a professional to help facilitate the conversations. Be patient, express how you feel to show them that it is ok to do so and keep trying. I promise you; it’s the best thing you can do.

Written By Mallory McGrath
Mallory McGrath is the Founder & CEO of Viive Planning, in Toronto, Canada, which facilitates conversations and fosters an appreciation among family members for end-of-life and legacy planning. Mallory is a mother, wife, daughter and granddaughter whose own chronic illness and pain have launched her towards a career in advocacy and planning.