From an excellent WSJ article by Ben Cohen interviewing Ron Shaich, billionaire entrepreneur; 

• “What can I do in the next three to five years that I will respect looking back from my deathbed?”
• “I imagine my body old and fragile, my breathing shallow, my life energy almost extinguished, he wrote in Know What Matters, his 2023 book.  I try to evoke the feeling I want to have in that moment – a sense of peace, completion and, most importantly, self-respect.  Then I ask myself:  What am I going to do now to ensure that when I reach that ultimate destination, I’ve done what I need to do?” 
• “I realized that the time to be having that review was not in the ninth inning with two outs.  It was in the seventh inning, the fifth inning and third inning.”

The most important question estate planners can ask their clients; If we (client, spouse, collaborative advisors) were gathered here today and you had died last night what would we be discussing?  The follow-up questions are situation and client specific.  The answers to the questions will help the advisors and the client to determine whether or not there are problems/issues that should be addressed today.  The degree to which the client is dissatisfied/unhappy with his/her current situation and the potential outcomes if premature death were to occur will determine how smoothly, quickly, and successfully the rest of the planning and implementation process moves forward.

I believe this is the most important question that we estate planners should ask every client now, not in the ninth inning with two outs.  It is the essence of what we do and, perhaps, the most productive thing we can do this year.

The WSJ article can be found by clicking here.