How to Have Difficult Conversations with Someone You Love


Not sure how to have a difficult conversation with someone you love regarding end-of-life planning? Discussing death and future burial arrangements can be challenging and uncomfortable for family members. How do you even begin these conversations with your loved one? What will they think? Will they start to panic and think there is something wrong, or worse avoid the topic completely?

It is never easy to communicate about end-of-life planning. You have heard it a million times, however, communication is key in these situations. While there’s no perfect time to talk about death, the sooner you start the dialogue, the more comfortable you will get. Eventually, your family will become more comfortable communicating about this process, your end-of-life planning and considerations.

What to Consider Before Starting a Difficult Conversation

Initiating these end-of-life planning conversations should begin well before an aging or terminally ill person can no longer make their own plans/decisions.

If you are the one planning, consider these questions and how you want to address them with your loved ones:

  • Will my family be taken care of?
  • Who will look after my pets?
  • Is my will up-to-date?
  • Is my estate plan finalized?
  • What are my wishes for end-of-life medical care?
  • Where are my end-of-life documents stored?
  • Who should be included in my care decisions?
  • How would I like to eternally rest?

The best thing to know when planning to have a conversation about these topics with your family members is that not everyone is comfortable openly talking about mortality. Make sure you approach each conversation with empathy and understanding of the other person’s emotions. The more patience and understanding you offer, the better things will go for everyone.

How to have Difficult Conversations with Someone you Love about Death and Mortality

The following are some ways of introducing these conversations with less resistance from your loved ones:

Hold many conversations

The discussion of death, even if it is far from the near future, can be overwhelming and heavy. It is best to have these difficult conversations in smaller chunks, instead of discussing every end-of-life prep topic in one moment.

Being honest and sticking to the facts, while allowing your family member to communicate their emotions about your planning is healthy. It is important for you to hold an open-ended dialogue that continues into more than one sitting. In addition, making tough decisions can be emotionally taxing, causing them to shut down. So, make sure you are not overwhelming them and make it clear that you will pick back up on the topic later.

Begin the conversation about something small

Dropping the “D” word without proper consideration for your family’s feelings will not end well. Instead of jumping right in, start with something small. If you immediately tell your loved ones that you have purchased a burial plot or have met with a funeral director for future planning, their immediate reaction may be shocking. They may think there is something wrong with your health, or that you are keeping something from them.

It is best to introduce the topic by explaining that you are working on getting different affairs in order for the far future. For example, you are handling future plans across the board like establishing a life insurance policy, safety deposit boxes, and other planning. Most people have life policies in place early on in life, so using this as a conversation opener for more difficult conversations is key. Introducing death and dying in small, digestible chunks can make the conversation more palatable and less likely to turn your loved one away from it.

Ways to Talk About End-of-Life Planning with Loved Ones

Communicate clearly and effectively. The way you frame your conversation can impact how your loved ones accept and react to your attempts to get these discussions going.

Contacting a professional to help you can also be beneficial. In most cases, hearing from a professional can take some of the emotions out of the process. For example, setting an appointment with a funeral home to talk about options with your loved ones is an effective approach to holding difficult end-of-life conversations.

You can also, use examples of friends or relatives who had significant issues or struggles due to poor planning. Talk about the consequences and how they could have been avoided.

Here are some topics you may want to establish with your loved ones:

  • Your end-of-life plans: funeral plans, burial/cremations plans, establishing life insurance policies
  • Where you want to live if independent living is no longer an option
  • What is to happen with your personal belongings
  • Property Power of Attorney
  • Health Care Power of Attorney
  • HIPAA Authorizations
  • Advanced Directives & Living Will
  • Out of Hospital DNR

Read more about pre-planning a funeral.

What are the best/worst times to have difficult conversations?

There is never a perfect time to have to talk about end-of-life planning. The best time to have hard conversations with a loved one is before you need to. Start planting these talks ahead of time.

The worst time to have a difficult conversation is in the middle of a crisis when things need to be decided on right then and there. Hasty decision-making tends to make things more stressful for everyone. However, try to talk in a safe space where there are few distractions. Make sure the person you are speaking with is in a good mental place to handle the conversation in a mature and productive manner.

What if the conversations are not productive?

No matter how careful you are, having these discussions may create conflict. People may feel attacked, so they display emotions of anger or sadness. These reactions are all very human. If the conversation goes south, take a break and continue the conversation at a later time.

Take advantage of times when the family is together

Some families do not live in close proximity but get together for special occasions or during holidays. Take advantage of those times. This way, everyone can be on the same page and know your wishes. This eliminates future stress and improves overall family communication.

Some good times that family is already gathered:

  • Thanksgiving
  • Holiday Seasons
  • Family Reunions
  • A Family Dinner

Be intentional about the best time to have this conversation. Be open with everyone. Know that you can keep it simple.

Ultimately, we can’t bear the thought of losing someone we love, yet we know that no one lives forever. The importance of having purposeful and meaningful end-of-life conversations is so your family does not have to stress after you have passed. Proper planning can save you and your loved ones lots of heartache, money, and regret. Now hopefully, you have learned how to have a difficult conversation with someone you love about end-of-life planning.

If you are ready to start end-of-life planning, a member of the Green Hills team can assist you and your family. Contact us online or give us a call at (310) 831-0311.