Talking about your will isn’t exactly a fun weekend activity, but trust us—it’s worth the effort. A little planning now can prevent unnecessary drama, hurt feelings, and stress for your loved ones later on. Think of it as an act of kindness and care for your family and for yourself. Given the natural feelings that can arise with this top, it may help to have a guide to start the process. Let’s dive in and give you some starting points.
Why communicating your will matters
It may be tempting to write a will and just have it be… I mean, do you really have to talk about it explicitly with your family members?
While having a will is essential for making sure your wishes are met once you pass, communication with those impacted is just as important. Here’s why:
- Prevents Misunderstandings: Transparency can help avoid speculation or misinterpretation of your wishes because they are hiring it from you directly. This also allows your family members to ask questions now and receive answers.
- Avoids Legal Disputes: By explaining your choices, you can reduce the likelihood of disagreements becoming costly legal battles. You can also nip any judgment, blame, or attempts to undercut your wishes directly.
- Helps Provide Emotional Closure: Hearing your intentions now allows your loved ones to process the contents and emotions that arise. It also shows how much you trust and love them, but share this with them openly.
How to approach the conversation
Let’s be honest—the conversation will likely be awkward and uncomfortable. It’s not a conversation many of us have often. To help ease some of the discomfort, try these steps:
Be intentional about time and place
Don’t surprise your loved ones in the middle of a birthday dinner. If possible, prime them by letting them know when, where, and why you would like to meet with them. Something like, “There is something I wanted to share with you—can we meet on Saturday morning at home?” This helps create a situation where everyone can feel as comfortable as possible. So, yes, definitely avoid holidays or other emotionally charged events.
Know your family
Who should know about your will and what’s in it? Now, be honest—how might they react? Use this information to decide if you want to start with one meeting with everyone or meet with each person (or a select few) individually first. This may depend on the personalities of each person or the content of your will. So, if you know one individual may react poorly or need more time to process, it could be helpful to meet with them first.
Frame the Conversation Positively
Begin with your general goal: “I want to share this now because I think it’s important to hear directly from me, and I will know you’re all cared for and on the same page.” Focus on your intention to share this now so you can be directly involved and have any needed discussions. As needed, stress that this is about clarity, not to scare, pass judgment, or show favoritism.
Be Clear To Be Kind
You might feel pulled to be more vague to spare someone’s feelings or circumvent a big emotional reaction. Don’t. Clarity is kindness and a sign of respect—trust that your family members can handle themselves. Use simple language to explain your decisions. Something like “We’ve chosen to leave the house to Jane because she lives nearby and has been taking care of it” instead of “I think you’ll all probably agree with who the house goes to, so that won’t be an issue.” Remember, the more everyone is aligned now, the less likely hurt feelings and arguments will occur when the will is enacted.
Plan for multiple meetings
This likely won’t be a one-time thing (unless you have good reasons for it to be). It is beneficial to allow your family members time to hear the information, process it, and come back for questions. Feelings of sadness, anxiety, fear, frustration, anger, relief, happiness, or jealousy can all crop up. Providing the space to deal with those emotions and logically process the content will be helpful.
Include professionals
Want to share the contents but don’t have the brain space or desire to answer all the nitty-gritty questions? Bring in backup! Have your lawyer or another professional present to answer the more logistical questions.
Make it personal
Share what you love about your loved ones and how that was part of your decision-making process. Things like, “Sloane, one of my favorite memories was rebuilding the VW Bug with you, and so I’ll want you to have it.” Tying in that emotional aspect lessens the transactional nature and allows your family to feel strongly connected to you.
Practice, Practice, Practice
Do you know what can help make things less awkward? Rehearsal! While it may seem odd to “rehearse” what you’ll say to loved ones, this will help you find the right words and minimize defensiveness or miscommunication. Turn to trusted friends, your partner, or even video yourself!
Checklist: What to prepare for the conversation
Alright, before you sit down with your loved ones, let’s make sure you have the basics covered:
- Have a Clear Copy of Your Will:
- Ensure your will is complete, signed, and legally valid.
- Consult with an attorney or estate planner to finalize the document if necessary.
- Discuss Decisions with Your Spouse or Partner First:
- Align with your partner to present a united front during the conversation.
- Schedule a Meeting or Individual Discussion
- Decide whether to communicate with everyone at once or in smaller, private conversations.
Final Thoughts
Talking about your will’s contents is not something we necessarily look forward to, and it probably will not feel natural. But, like many things, getting to the other side, you’ll probably be relieved you did! It’s a necessary step in helping set your family up for success in a future without you. Through thoughtful planning, being transparent, and approaching the conversation with empathy, you can have a productive conversation with your loved ones and give yourself some peace of mind.
Frequently Asked Questions (FAQs) about communicating the contents of your will
We know this isn’t easy. Here are some more FAQs to help you navigate this process.
Q: Do I have to tell everyone what’s in my will?
A: No, not necessarily. You’re not obligated to disclose every detail or tell the people in your will they’re in your will. However, sharing key decisions can help set expectations and avoid surprises.
Q: What if someone reacts badly?
A: Stay calm and acknowledge their feelings. Be curious and don’t assume what they may be feeling, but if they are not in the headspace to have a further conversation with you, it’s okay to take a break or hold firm boundaries. For example: “I understand this might be disappointing, but this decision reflects what we believe is best for everyone.” Remind them that your choices are based on careful thought and consideration.
Q: Should I hold a formal family meeting?
A: It depends on your family. What are the pros and cons? Will it be more beneficial for the family to hear it all at once so there is no game of telephone? Or will having everyone in the room just escalate feelings unnecessarily? If there are no strong cons to either choice, the ideal would be a meeting with everyone present to ensure everyone hears the same information at the same time, as well as the questions that may be brought up.
Q: What if I change my will later?
A: You can (and should) update your will later if things change. You should also keep your family updated about significant changes to avoid confusion down the road. A simple follow-up conversation can suffice.
Dr. Vivian Oberling is a licensed clinical psychologist with degrees from UCLA, Harvard, and Stanford. In her private telehealth practice, she works with adults navigating anxiety, identity shifts, and relationship dynamics—whether they’re dating, partnered, or parenting. She also provides executive coaching and behavioral health advisory support to tech startups and legal tools reshaping how we think about love, marriage, and psychological safety. Dr. Oberling combines 10+ years of clinical expertise with modern, real-world insight to help people move through uncertainty with clarity and connection.
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