How to Have the “Hard” Conversations About Estate Planning
Plus: 10 Conversation Starters That Actually Work
By Katie Katz, Attorney and Founder of Mitzi, and Natalie Schreter, LCSW, Co-Founder of Hudson Mental Health
If you’ve ever tried to talk about estate planning with your family and felt the room tense up, shoulders stiffen, eyes dart to the floor, someone suddenly remembers they have to check on the laundry - you’re not alone.
Talking about what happens when we’re gone, or if we can’t make decisions for ourselves, isn’t exactly light conversation. But here’s the thing: the conversations you avoid now can become the conflicts your family lives with later.
We’re here to help you change that.
Why These Conversations Matter More Than You Think
Estate planning isn’t just about “who gets what.” It’s about protecting the life you’ve built, the people you love, and the values you hold dear. And when you bring those wishes out into the open, you:
Reduce the risk of misunderstandings, hurt feelings, and drawn-out legal battles
Give your family clarity and direction in a crisis
Keep your voice in the room—even if you can’t speak for yourself
As Natalie frequently tells her clients, “Anxiety often fills the space where information is missing.” When you talk openly, you take away that uncertainty. Anticipation is an unavoidable part of difficult conversations but you don’t have to let fear operate in control.
Why It’s So Hard to Talk About
Even with the best intentions, these conversations can trigger:
Fear – of illness, death, or losing control
Old family dynamics – sibling rivalries, unresolved resentments, or generational differences in talking about money and mortality
Guilt or discomfort – feeling like you’re burdening loved ones
The good news? Handled with careful planning and consideration, you can make these talks less overwhelming—and even (dare we say) bonding.
Best Practices for a Productive Planning Conversation
We’ve seen families transform these “hard talks” into moments of connection. Here’s how:
1. Start Before There’s a Crisis
If you wait until someone is sick or in the hospital, emotions are high and time is short. Instead:
Choose a neutral time and relaxed setting (like a walk or Sunday brunch)
Let everyone know the topic in advance so it doesn’t feel like an ambush and holds you accountable
Plan out what is important to you as a guideline for the conversation. Writing your thoughts out will help you organize them.
Make it bite sized. When something feels too big, overwhelm sets in and avoidance becomes the strategy.
2. Lead with Your “Why”
Open with why this matters to you:
“I want to make sure no one has to guess what I’d want in an emergency.”
“I’ve seen how stressful it can be when families have to make decisions without a plan—I don’t want that for us.”
Your motivation sets the tone—it’s about care, clarity, compassion, not control.
3. Be Clear and Specific
Vague statements (“I trust you’ll figure it out”) invite confusion. Instead:
Name decision-makers in writing and tell them directly
Share the basics of your plan (e.g., healthcare proxy, guardians for kids, how to access important documents)
4. Keep Emotions in the Room
Natalie’s tip: make space for feelings that will inevitably live alongside these conversations – acknowledge feelings without letting them derail you.
If someone gets upset: “I hear this is hard to talk about. Let’s take a breath.”
Check in with yourself about what meaning you are making of their emotions and remain curious
Validate their perspective before moving back to the plan
5. Make It a Two-Way Conversation
Ask your loved ones what matters to them, too. Sometimes these talks reveal shared priorities, unspoken fears, or family stories you’ve never heard.
Tools to Make It Easier
Written summaries – Send a short follow-up email after your talk so no one forgets key points.
Professional facilitation – It doesn't have to fall on you to both be a participant in the dialogue and the facilitator. Let someone else take on that responsibility when needed. In high-conflict situations, consider having a neutral third party (lawyer, therapist, mediator) present.
Step-by-step guides – Use tools like Mitzi to outline what decisions need to be made, in plain English.
If the Conversation Gets Stuck
Natalie recommends:
Press pause – You don’t have to cover everything in one sitting
Shift the focus – Talk about shared values and goals (“We all want what’s best for Mom”) before diving back into specifics
Keep the door open – End with: “Let’s come back to this next week when we’ve all had time to think.”
The Payoff of Leaning In
When you have these conversations now, you give your family:
A clear roadmap
Fewer reasons to argue
More space to focus on care, connection, and honoring your wishes
Leaning in is a gift to yourself as well and can alleviate unsettled/lingering feelings of this hanging over your head as a task not done.
Planning isn’t about predicting the future—it’s about giving the people you love the best chance to navigate it with confidence, compassion, and unity.
Katie’s Final Word: Start the talk. Then finish the job. Conversations open the door, but only a proper, signed estate plan keeps your wishes from being argued later. If it isn’t written and executed, it can be disputed. When it is, your voice stands, your family has a clear roadmap, and you avoid wasted money, time, and heartache. Begin small. Speak from the heart. Put it on paper. Share it with the right people. Update it as life changes. Your future self, and your people, will thank you.
Natalie’s Final Word: Estate planning conversations can be challenging, but they also present an opportunity to bring families closer together. When approached with clarity, respect, and compassion, these discussions not only ensure that wishes are honored, but also help preserve trust, understanding, and can safeguard the long-term stability of family relationships.
10 Conversation Starters That Actually Work
Because sometimes the hardest part is just knowing how to begin.
“I’ve been working on my own plan, and I realized I want to share it with you.”
→ Shows you’re walking the walk, not just telling others what to do.“Can we set aside some time to talk about what we’d all want if something unexpected happened?”
→ Neutral, forward-looking, and includes everyone.“I read something that made me think about what matters most to me—and I’d love to know your thoughts too.”
→ Invites mutual sharing, not a one-sided lecture.“This isn’t about control—it’s about making things easier for you if I can’t speak for myself.”
→ Reassures them of your intentions.“I know these topics can be uncomfortable, but I care too much to leave things unsaid.”
→ Names the discomfort while affirming your care.“I’ve seen how hard it can be when families have to make decisions without a plan. I want ours to be different.”
→ Connects the conversation to a real-life lesson.“Here’s one decision I’ve already made—what do you think?”
→ Gives them something specific to respond to, which is less overwhelming.“I want to make sure we’re all on the same page so there’s no confusion later.”
→ Frames the talk as teamwork, not confrontation.“If something happened to me tomorrow, do you know where to find my important documents?”
→ A gentle nudge that’s practical and immediate.“Can we have this conversation now so we can get back to the fun stuff?”
→ Lightens the mood and signals it’s a short, necessary step.
You Don’t Have to Do It All Today—Just Start
If you’ve made it this far, here’s your next small step:
✓Take our quiz to get a free, personalized list of the planning documents you may actually need
✓ Forward this article to someone you love who thinks estate planning isn’t for them
✓ Bookmark this page—your future self will thank you
Planning is one of the most caring things you can do. Let’s make it easier - one small step at a time.
