Top 30 Questions - To Help Initiate Meaningful Conversations
Probing Legacy Questions
Created by Greg Barnsdale, author of ‘Do Not Ignore Your Mortality - Practical Advice From a Funeral & Financial Insider’

Basic ice-breakers:
  1. Did you know that end-of-life planning can help reduce the stress of aging?
  2. Did you know that end-of-life planning can enhance family harmony?
  3. Did you know the results tend to leave survivors more financially & emotionally resilient?
  4. Have you had a close family member or friend die?
  5. Do you know anyone who openly talks about what they want done after they’re gone?
  6. Have you discussed with your family what you want done with your body?
  7. Do you want to be cremated, buried, recycled or composted?
  8. Why do you prefer that option?
  9. What type of funeral would you like?
  10. Who is to be in charge of wrapping up all the details of your life?
  11. What if that person is unable to fill the role?
  12. What are some of the challenges you’ve heard of survivors having after a death?
  13. Did you know that only about half the adult population of Canada and the U.S. has a valid and current will?
  14. Do you have a will?
  15. Is it valid & easily found?
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Advanced, for more in-depth conversations:
  1. Did you know that end-of-life planning is one of your most loving gifts?
  2. Do you know what happens when someone dies without having a will in place?
  3. Has anyone close to you acted as an executor?
  4. Are you familiar with the responsibilities of an executor?
  5. Did you know executors can be sued?
  6. Are you familiar with the circumstances of when a lawyer should be hired for will planning?
  7. Would you like to give your family & close friends one last chance to see you & say goodbye?
  8. Are you familiar with Advance Care Planning?
  9. Do you have a medical directive in place if you cannot communicate?
  10. Are you likely to be an executor or a power of attorney for someone?
  11. Did you know organs and tissue can be donated after death, regardless of age?
  12. Are you familiar with medical assistance in dying? (MAiD)
  13. What are your thoughts regarding this way to die?
  14. Are you familiar with complicated grief?
  15. Have you heard of the Death Positive Movement?

The above was created to help more people engage in heartfelt conversations when minds are clear and time is plentiful. Exploring authentic feelings is essential. These can be a good starting point. The key is to be proactive. 

Resources for End-Of-Life planning
Click the logo to visit the resource website.
CEA's are experts in their own field but also have broad practical knowledge of everything the executor needs to know. Uniquely equipped to steer executors away from potential problems and toward the professionals they need.​

​STEP is a global professional body, comprising lawyers, accountants, trustees and other practitioners that help families plan for their futures.
Established in 1995, FP Canada is a national not-for-profit education, certification & professional oversight organization working in the public interest. FP Canada is dedicated to championing better financial wellness for all Canadians by leading the advancement of professional financial planning in Canada.
The Canadian Bar Association champions Canada’s legal profession and the rule of law in Canada. We are the largest association for legal professionals in the country, representing over 40,000 lawyers, judges, notaries, academics & students.
The ABA was founded in 1878 on a commitment to set the legal and ethical foundation for the American nation. Today, it exists as a membership organization and stands committed to its mission of defending liberty and pursuing justice.
FSAC is the national voice representing Canada’s funeral homes, cemeteries, crematoriums, suppliers, and other professionals in the deathcare profession. A dedicated ally and advocate, FSAC champions the value of meaningful end-of-life services through education, public awareness, legislative guidance, and advocacy.


​The Personal Fiduciary Certificate is the gold standard for anybody acting in the capacity of a Personal Fiduciary such as Powers of Attorney, Executors and anybody else expected to act in a fair, honest and transparent manner.
An innovative & comprehensive website offering all sorts of funeral related services to help preserve memories & simplify planning. 
Peacehold’s pre-planning service helps organize & prepare your estate documents before they’re needed—saving your family time, stress,  and confusion during an already difficult time. For a one-time fee, they provide a comprehensive, customized package that guides your representative through hundreds of administrative tasks after your passing.
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The Legacy Collective supports and uplifts those who guide others through life’s final transition. Regular events around Ontario advocating death positivity and curiosity. 

Fiduciary Literacy educates and builds confidence: acting as a fiduciary comes with countless responsibilities,  it's easy to stray from following fiduciary best practices, particularly when Canadians have not had the opportunity to fully learn what those responsibilities entail.  

​Adrianna Prosser, also known as Lady Death Doula on social media, is a Toronto located death doula, grief educator, soul companion, and mental health advocate ready to support you.
For testators wanting to ensure their estates are well prepared, so as not to be a burden on their executors, CEAs can offer tremendous value.
​Do Not Ignore Your Mortality
​Practical Advice From a Funeral & Financial Insider
By ​Greg Barnsdale, Licensed Funeral Director
and ​Certified Financial Planner

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