What if the most loving thing you could do for someone is start a conversation you've been avoiding?

In this episode, Michael Reddington sits down with Cory Fosco, a 34-year veteran of the eldercare and healthcare technology industries, author of The Question of When, creative writing teacher, and VP of Enterprise Sales. Cory brings a rare combination of frontline caregiving experience, social work roots, and sales leadership perspective to one of the most universally avoided topics in family life: planning for the care of aging loved ones before a crisis forces your hand.

This conversation goes far beyond eldercare. Cory unpacks why denial and guilt keep families frozen, how the fear of messing up drives worse decisions than the fear of missing out, and why having a conversation is fundamentally different from making a decision. The parallels to sales, leadership, and any high-stakes relationship are impossible to miss.

What You'll Learn in This Episode

• Why waiting for the "right time" to have a care conversation is itself the mistake
• How families that do the homework in advance make better decisions under crisis pressure
• The difference between "fear of missing out" and "fear of messing up" and how it shows up in caregiving and sales
• Why expressing love through preparation changes how families approach difficult conversations
• How having a conversation and making a decision are not the same thing -- and why that distinction matters
• What the "When Readiness Checklist" is and how to use it to assess where your family stands
• Why "it's better to do right than to be right" applies equally to caregiving, leadership, and sales
• How to give people around you permission to make mistakes by modeling it yourself

Chapters

• (00:00) Introduction to Cory Fosco and A Question of When
• (05:05) Why Families Wait Too Long to Have the Conversation
• (07:28) How We Compensate and Make Excuses for Loved Ones
• (10:57) How to Optimize Preparation Time and Remove Stress From Big Decisions
• (14:18) The Fear of Messing Up and How to Take the Risk Off the Table
• (24:00) Listening as the Foundation of Caregiving, Sales, and Leadership
• (27:39) Why It's Better to Do Right Than to Be Right
• (33:13) How the Book Is Structured to Meet Families Where They Are
• (50:21) Core Principles for Navigating Difficult Family Conversations
• (52:31) How to Find Cory and Access His Resources

About the Guest

Cory Fosco has spent over 34 years working at the intersection of long-term care, healthcare technology, and family decision-making. He began his career as a social worker, moved into admissions and senior care leadership, and now serves as VP of Enterprise Sales for one of the largest EMR platforms serving skilled nursing facilities. He is the author of A Question of When, a guide for families navigating eldercare decisions, and teaches creative writing to a wide range of students including the blind and visually impaired community through Second Sense in Chicago.

Links and Resources

• A Question of When by Cory Fosco - https://a.co/d/0ciiLRpc
• https://www.coryfosco.com
• From Values to Action by Harry Kramer - https://a.co/d/06m0h7lH

Sponsor Links:

• InQuasive: http://www.inquasive.com/
• Humintell: Body Language - Reading People - Humintell
• Enter Code INQUASIVE25 for 25% discount on your online training purchase.
• International Association of Interviewers: Home (certifiedinterviewer.com)

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