Any person who is seriously ill is likely to have had a conversation with their family and/or attorney about advance healthcare directives such as wills, powers of attorney, trusts, etc. These conversations, while important, are the usual and expected way we engage with ill family members.

However, there are other even more personal conversations that need to happen when someone is seriously ill.

Here are five of the most important, and compassionate, questions to ask a family member to help facilitate them in having the best quality of life possible.


1. What is your understanding of where you are and your illness?

This is a collaborative question that helps both the person asking and the person answering get on the same page about the reality of the situation.

It’s not uncommon for children and spouses to just assume their loved ones understand more about the situation than they do.

Emotional reasons or cognitive impairment can mean a family member may not have fully grasped or come to terms with their situation or what it means for their future.

In some cases, the opposite can also be true. Family members may assume their loved one understands virtually nothing about their situation.

Asking this question helps move past assumptions and clarifies the reality of the situation for both parties.

Additionally, the dialogue that comes out of asking this question allows the other person to talk about their comprehension of the situation.


2. What are your fears or worries for the future?

When a loved one suffers from an illness, it’s natural for them to start thinking about their own mortality and what lies ahead.

“What are my kids going to do without me? Is my wife going to have enough money to live? What if I miss my daughter’s wedding?” These are the type of thoughts that people are often encumbered with in this situation.  

The problem is that if these concerns are not given space to be expressed, then nothing can be done to help address them.

Even after being poked, prodded, and run through the medical system, many people in this position have never had the opportunity to simply talk out their worries and fears. When they are given the chance, the experience can be cathartic and empowering.


3. What are your goals and priorities?

This is the ultimate goal of what caring for someone with an illness is all about: giving that person the opportunity to articulate what’s important so the people around them can support those goals and priorities.

Too often we assume our loved ones have the singular goal of getting better. The problem with this assumption is that it ignores the likely scenario that they have other goals as well that haven’t been addressed.


4. What outcomes are unacceptable to you?

Of all the questions, this can be the most difficult one to discuss. It requires delving into what could happen in the future and what your loved one wants as their health circumstances progress.

Too often, it’s the doctors and specialists debating amongst themselves, according to their values, what is right for the patient.

But your loved ones deserve a choice. It’s critical to give the patient the opportunity to speak up about what they’re comfortable with when their boundaries are at risk of being crossed.


5. What would a good day look like?

The opportunity to say out loud what a good day looks like, with the hope that it can truly be achieved, is fundamental to the human spirit. This question is about what truly, in a person’s heart, makes them happy.

When a loved one or care provider knows the answer to this question, they can work in service of that goal.

I experienced this with my father who, during his ongoing illness, responded to this question by saying, “I just want to go to lunch with my children.” I knew I was able to take action and help make his day just a bit brighter despite everything else going on.

Unfortunately, in healthcare today, almost everything is imposed upon the patient, and often, the sicker you become, the more disempowered you are.

The sad reality is that many people die on everyone else’s terms. These five questions of empowerment are meant to generate deeper conversations about the quality of the end of life so the person can die on their own terms.


Douglas J. Wenners is the cofounder and CEO of Prospero Health, providing home-based care for people living with serious illnesses. Doug is a strong advocate for changing the way society views healthcare from being system-focused to patient- and family-focused. Learn more at

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