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As we approach the holiday seasons, you’ve likely got family and friends on your mind. You’ve got a whole list of topics to catch up on, but we’d be willing to bet that estate planning probably doesn’t make it on that list. 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 difficult conversations.

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is a collaborative divorce attorney with over 15 years of experience helping families navigate complex life situations. We chatted with her to get her perspective on how to have difficult conversations around death and estate planning - here’s what she had to share:

��������: Anna-Marie, what do you think makes these conversations so difficult?

Anna-Marie: The truth is, the conversation is scary because the topic is scary. In particular, dealing with estate planning and wills, you’re having a conversation about your loved ones and them passing and what that looks like. It’s inevitable that it circles back to your own life, causing you to think about your own mortality and reflect on your own relationships. It’s interesting to see how these conversations about end of life care make people pause and think about their current relationships. When you think about what the end looks like you want to make sure you’re having meaningful relationships with your loved ones! It also brings up the point of aging and that’s really scary for people. I don’t blame people for feeling the conversation is difficult and it’s important to know that it’s ok to be afraid. 

��������: In your experience, what is the best way to begin an awkward or difficult conversation?

Anna-Marie: What we suggest for our family law clients is very much the same for having end of life conversations. We always say to start with what we hope to accomplish and start at the end and work backwards. The conversation is stressful. We usually recommend starting with I statements (I’ve noticed that..., I feel that… etc.) as it can make the conversation feel less confrontational. Then we talk about the main issues - is it estate planning? Is it divorce? The tone should be respectful and compassionate, so it does not become adversarial.

It’s also ok if it’s a short conversation! If we can only tackle 1-2 important issues at a time that’s fine, we can reconvene, but it’s important to get the dialogue going. It’s easy to go astray with these conversations, so we often coach clients on how to circle back on the topic at hand and  when it’s time to end the conversation and start it up again later if needed.

��������: Do you think it’s better to plan a time and setting in advance or naturally weave it into an ongoing conversation?

Anna-Marie: I always suggest planning a time and place ahead of time and to plan time to recover afterwards from what can be an emotional and difficult conversation. You want to give yourself a chance to decompress afterwards, which can be difficult to do in a crowded restaurant. It’s ok if you need to have multiple conversations, but make sure to set time for follow up.

You may even want to have the conversation with a glass of wine or a latte to help make the situation feel more comfortable.

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

Anna-Marie: What we have found works well is to try and make the conversation ‘less scary’. We sometimes encourage our clients to use anecdotes, such as, “My friend Sally told me she X,Y, and Z and it was really great because of X,Y,Z etc”. This brings the information to the conversion but in a less scary way.

��������: This year, we’ve had to take a lot of our interactions virtual. Any tips on tackling these conversations remotely? 

Anna-Marie: It’s much easier to read body language in person, words can be softened or take on a different meaning which can be difficult to ascertain over zoom. On the other hand, what I like about Zoom and video chat is that you can read micro facial expressions where you can see their face up close, which you wouldn’t normally get to do in regular settings. You actually get to see a bit more facial expressions which I actually think is a good thing. 

It’s important to maintain eye contact when having these conversations to share that this really is an important conversation and that you’re really listening. You want to ensure it’s not just one-sided conversation if possible - remember to sit back and listen. It’s easy to get on Zoom and just zoom through your points quickly and say ‘Have a good day!’. But it’s important to keep the tempo going because the other person needs to be heard and respected - they also have feelings that need to be expressed.

Also we should be mindful of Zoom/video chat fatigue, it can be really difficult and exhausting. It’s perfectly acceptable to have multiple conversations and is in fact recommended, because Zoom fatigue is a real thing!

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

Anna-Marie: I love TEDTalks and they have the most interesting things about different topics, including how to tackle difficult conversations. So that’s a really great place to start!

��������: Do you have any final pieces of advice?

Anna-Marie: I’ve noticed what tends to happen with clients when they’re getting ready to have these conversations, is they forget about the anxiety that builds up ahead of time. Take some time to meditate or relax - that anticipatory anxiety can sometimes be worse than the conversation itself. If you have tools to help ease you through it, any sort of relief is helpful. Finally, remind yourself that you’ve really accomplished something important by engaging in this conversation and take time to reflect that you’ve taken the important steps. 

is a collaborative divorce attorney and founder of with over 15 years of experience helping families navigate complex life situations. After spending years litigating cases in court, Anna-Marie identified that this process was dated, expensive, and unnecessary – there’s no need for many family cases to go to court. She has a passion for innovative, out-of-the-box problem solving and not only is able to help her clients as a lawyer but also as a strategic advisor.