Questions and Conversation Starters

Questions and Conversation Starters

Below are sample questions from our book. If you are interested in all of the questions and conversation starters, you can purchase the book here.  The questions are divided into the following sections:

  • Getting to Know Them Better
  • Enhance and Mend Relationships
  • Finding Peace and Acceptance
  • Creative and Positive Aging
  • After a Serious Diagnosis
  • Loving Them Goodbye

Getting to Know Them Better:

Family History and Heritage:  Would you tell me what’s most important to know about this family before I was born? It might be a person, event, values or traditions that impacted our family in some way.


  • What was it like for you growing up in our family?
  • What positive memories, key events, and milestones stand out for you?
  • What made our family unique and what strengths stand out for you?

Childhood friend: Please share a story about a childhood friend who made a difference in your life. Talk about this friendship and the person.

Follow up:

  • How did you meet?
  • What did you do together?
  • What positive impact did this person have on your life?
  • What was most rewarding about this friendship?

Enhance and Mend Relationships

Best of Our Relationship: As you look back on our relationship, tell me about a time that stands out as a high point – a meaningful and important story that captures the best of our relationship.


  • What were we doing?
  • What stands out as important and essential about our relationship?
  • What do you value about that aspect of our relationship?

Common Ground: We all view the world in different ways and have different values and beliefs. We live our lives in different ways. Differences can separate, but common ground unites us. What are the important things we have in common? Would you tell a story about a time when these commonalities added to our relationship?


  • What do you value most about these commonalities?
  • How can we build on these commonalities to strengthen our relationship?


Finding Peace and Acceptance

Important Contribution: Without being modest, what do you consider your most important contribution?  It could be related to your family, work, community, or the world. What is this contribution?


  • What happened?
  • Why do you consider this your greatest contribution?

Reconnecting with People: As time goes by we lose contact with people who were important to us. Sometimes certain people made a major contribution to our lives. Yet we never voiced our appreciation. Are there people that you would like to contact and renew your relationship?  If so, who are they?


  • What would be important for you to tell that person?
  • Is there anything you want or need to hear from them?
  • What would renewing that connection mean to you?


Creative and Positive Aging

Benefits of Aging: Although there may be some new physical limitations with aging, there are also advantages of maturity and experience. What is better now than when you were younger? Tell me a story illustrating the benefits of age as you have experienced it.


  • What are some of those benefits?
  • How are you using those advantages to instill vitality and joy into your life?
  • What more might you do?


After a Serious Diagnosis

Making Sense of the Diagnosis: Any serious diagnosis is scary and raises many questions, thoughts, and feelings. Talking and sharing can help. What are you experiencing?


  • What questions do you most want answered?
  • How might those answers be helpful? What would you do with the information?
  • If you had access to any medical expert what questions would you like to ask?


Making the Most of this Time: Facing a serious illness is a wake-up call.  Recognizing that life is finite reminds us to pay attention and make life-giving choices. What is most important to you at this moment?


  • Based on what it is you value – what actions, decisions, choices, and risks do you want to take now?
  • How will making that decision or choice keep you focused on what’s most important to you?


Loving Them Goodbye


Legacy: Most people hope their life has mattered and that they have made a contribution. They hope it will be recognized and celebrated. What are your hopes for a legacy? What do you hope people will remember about you and build upon?


  • What do you hope we will celebrate most about you?
  • What kind of celebration of your life or memorial would honor you most?
  • When you think of your legacy, what do you expect we’ll remember and honor most? Is that what you want or is there something more?


Anticipating Loss: You might hear the dying person talk about something or someone they’ll miss. They may also seem particularly quiet and sad. If so this is one way to invite them into conversation about the losses they are mourning.

  • What have you loved or appreciated most about …?
  • Tell me about ….
  • What are your concerns about …?
  • What are your hopes for …?