Ask An Expert: Estate Consultant, Debbie Stanley’s Tips For Uncomfortable Conversations

3 minute read
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    With the rollercoaster that has been 2020, we understand that estate planning probably isn’t at the top of your mind right now. However, discussing our end of life plans and wishes is one of the most important conversations we should be having with our loved ones.

    We’re helping you broach the topic of estate planning this holiday season so you can finally have the difficult conversations that you’ve been putting off. We connected with some experts to get their suggestions and advice based on their personal experiences.  

    All our expert contributors have a different point of view that we’re thrilled to share with you. However, discussions around estate planning are as unique as you, so we always recommend taking into consideration the dynamics and experiences of you and your loved ones, when approaching these difficult conversations.

    We sat down with Debbie Stanley, a partner at Estate Transition Planners Canada, to discuss her opinions around death, estate planning, and starting those uncomfortable conversations – here’s what she had to say: 

    Willful: Debbie, what makes these conversations about death and estate planning so difficult?

    Debbie Stanley: I think that they’re so difficult because, as humans, we fear the unknown and as such, we try to figure it out. I mean, there’s an app for everything nowadays but there isn’t one for the afterlife. Death is this unknown thing that will eventually happen, it’s not “if I die” but, rather, a matter of “when I die”. So, having these conversations is hard because we don’t know what happens and it’s easier to pretend like it won’t happen or at least pretend that we can delay the inevitable. We’re afraid of having these conversations, and that's why it's so hard. 

    Willful: What do you think is the best way to begin an awkward or difficult conversation? 

    Debbie Stanley: There are many different approaches I would recommend. Number one is to use current events as an excuse. For example, right now we’re in the middle of a pandemic, so we could use this as a conversation starter, “Hey, this really got me thinking, if something were to happen to me, these are my wishes for my health care,” and get the ball rolling. 

    Another approach I recommend is using recent Hollywood events. Alex Trebek just passed away, “Did he have a will? I should get a will done”. Use these conversations as a catalyst to start the conversation. So, you aren’t starting about you, but rather starting with a different topic and from there you can branch off into bigger topics but it all ties in with the ultimate goal of wanting to communicate with your family your estate plans and wishes. 

    Willful: Is it better to plan a time in advance or naturally weave it into an ongoing conversation?

    Debbie Stanley: It all depends on you. Personally, I am a planner so I would schedule in advance, you can make it an event and invite everyone with the intention to talk about it. However, it also depends on your family. If you have family members that are more shy on this sort of thing (like my dad) perhaps it's better to naturally weave it into a conversation. It really depends on your situation — how important it is that you get through certain topics, or do you prefer that it takes a course of time and you’re just naturally weaving it into a conversation. 

    Willful: Many people avoid conversation around wills and death in an effort to not ‘bring down the mood’. How do you suggest making the topic less scary?

    Debbie Stanley: You don’t have to make it about death — it can be about wishes, it can be things that you’d like/don’t like! For example, I like to say “I really hope people wax my eyebrows if I'm in the hospital”. It doesn’t have to be all doom and gloom. Try easing your way into these conversations by keeping things simple- get to know each other without even bringing up death. 

    The other thing too is that sometimes it's better to rip the band-aid off. Let everyone know that you have to have this difficult and uncomfortable conversation with them, but let them know that it doesn’t need to dominate the entire time. What most people don’t consider is that it can be a short conversation and then we can move on to other things. In fact, it's even better to have lighter conversations lined up after that. Keep it short and simple. 

    You can also break these conversations into segments. So, if you have a pet for example, just talk about the pet and what are your wishes for the pet during that conversation. And then at another time, you can move onto a different topic. 

    Willful: What is the best way to have a discussion with a family member who may be avoiding/not want to have the conversation?

    Debbie Stanley: For example, with my Dad, when I was making it about him— what were his wishes, what he wanted— he was more reluctant to talk about it. When I flipped it around and started talking about my own wishes, explaining that updating my will got me thinking about telling my loved ones about my wishes, it put everything into a different perspective for him, and suddenly he was more open to talking about it. I was telling him about my thoughts and my feelings and he was listening and made it less about his death. People will listen because they want to hear about what you have to say and it's less daunting for them because the focus is more on yourself and not them.  

    Willful: Is there a better environment/setting to have these types of conversations?

    Debbie Stanley: Again, it depends on your family. While having these types of conversations at home is nice, because it’s cozy and everything feels comfortable at home, your family may not want to associate their home as a place where they talk about death. Some families insist on meeting at a law firm since it’s a neutral place. By having these conversations in a neutral, professional setting, it won’t get as emotional and will feel more contained. Estate planning is not one-size-fits-all and neither is having these conversations, it all depends on what’s best for your family. 

    Willful: This year, we’ve had to take a lot of our interactions virtual. Do you have any tips on tackling these conversations remotely? 

    Debbie Stanley: We’ve certainly embraced the art of virtual meetings with things like Zoom, and Google Meets. Utilizing those tools are definitely great and can also be a great place to have these conversations. It leaves you with the option to just exit the conversation if you wish, though I don’t recommend running away from the conversation. While it is better to have these discussions in person, where you can see them and pick up on things like body language, you can still have them virtually. You can even prepare your family in advance by sending something like a kit with a conversation starter book ahead of time and then meet virtually to make it more approachable. 

    Alternatively, you can have some socially distanced meetings. Like go meet in a park, or go for a walk. The whole point is to make it more comfortable for you and your loved ones, and not just a typical sit down and talk about death. 

    Willful: Are there any tools or resources you recommend to further help people with these conversations?

    Debbie Stanley: There’s a really great resource - Advance Care Planning and they have a workbook of questions of conversation starters. They’re very organic questions, like “What values do you have”, to let you get to know someone better. When talking about estate planning, we focus on the nitty-gritty stuff and we forget about the person. These workbooks are a great resource because it makes you think differently about starting these conversations. 

    Additionally, following companies that are on the forefront like Willful. Consider seeking out people or companies on the internet that are trying to change the industry to make estate planning and talking about death more normalized. This is also the goal of my blog,, to help families get comfortable with talking about the uncomfortable. 

    Willful: Do you have any final pieces of advice?

    Debbie Stanley: My piece of advice would be to think of your whole plan as your legacy. You wouldn’t want your family to remember how disorganized you left everything for them. I would advise you to have your estate plans in order so that your family can remember all the good times they had with you, instead of associating your memory with a mess of paperwork. 

    Debbie Stanley is a partner at Estate Transition Planners Canada.  ETP Canada is a firm that specializes in estate administration and hands-on support for Executors who are currently taking on that role.  Additionally, they also act as a Professional Executor for your estate.

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