The Practical Planner – Episode Summary

Podcast: The Practical Planner
Episode: Helping Clients Leave a Legacy and Facilitate a Family Meeting with Derrick Kinney
Date: September 9, 2025
Host(s): Thomas Kopelman & Anne Rhodes
Guest: Derrick Kinney
Theme: Reimagining Estate Planning: Focusing on Facilitating Legacy and Meaningful Family Conversations

Episode Overview

This episode delves beyond the technical side of estate planning, exploring how advisors can help clients create lasting legacies, not just distribute wealth. Derrick Kinney, a veteran financial advisor, shares his hands-on experiences facilitating “family meetings” and having the hard conversations that make estate planning truly impactful. The discussion gives practical frameworks, language, and mindset shifts to help advisors deepen client relationships and ensure their clients’ values are part of their legacy.

Key Discussion Points & Insights

The Emotional Core of Estate Planning

• Estate planning is often “boring” for clients until it’s personalized with emotion and meaning. Derrick Kinney shares how connecting estate planning to a client’s legacy and family impact transforms it.
• Legacy isn’t just about money. Both Derrick and Anne highlight that clients care deeply about how they're remembered—the values and stories behind the wealth matter most.
  • “Money is really just a conduit to being able to do something with it, not necessarily for its own sake.” – Anne Rhodes (10:25)

Notable Story: Dr. Bob’s Family Meeting ([01:55]–[06:29])

• Derrick shares a moving personal account of facilitating a living “family meeting” for Dr. Bob, a terminally ill client. The goal was to give Dr. Bob’s family an opportunity to express love and to hear his legacy, with the meeting recorded for the future.
  • “He wanted to take some time to tell you, each of you, how he feels about you and to give him a chance to talk about his values and what's important to him...We wanted to have a record of it.” – Derrick Kinney ([02:58])
• The result was lasting gratitude and an emotional impact that extended years beyond Dr. Bob’s passing, showing the power of such gatherings for both practical clarity and family healing.

Facilitation: The Advisor’s Unique Role

• Advisors as “living estate planning documents” ([12:01]): Derrick emphasizes that it's the advisor’s presence and words—not just documents—that spark action and deepen meaning.
• Words equal wealth: The language and tone advisors use can determine whether clients are receptive or resistant. Confidence and empathy—coupled with good timing—are crucial.

Handling “The Conversation”

• Normalize talking about death as part of the planning process, not a taboo.
• Prompt clients with legacy questions—what do you want people to remember about you? Often, this inspires clients to start living out their ideals more fully.
  • “It was like this living eulogy that they wanted to practice every day.” – Derrick Kinney ([08:28])

Tactics for Sensitive Conversations

1. The “Crazy Question” Framework ([16:22]–[19:02])

   • Position tough topics with phrases like “Can I ask you a crazy question?” to lower defenses and gain permission to discuss delicate issues. (E.g., discussing guardians for young children.)
   • Gain explicit permission to broach uncomfortable territory, making it easier for clients to engage without feeling ambushed.

2. Set the Physical and Emotional Stage ([19:40])

   • Schedule in advance (“In our next visit, would you be willing to talk about a crazy and probably very uncomfortable topic?”).
   • Avoid “shock and awe”—never blindside clients. Use reminders so clients come prepared.
   • Use language that fosters warmth (“visits” instead of “meetings”) to reduce resistance.

3. When Only One Spouse Attends ([22:26])

   • Insist on both partners being present for legacy-related conversations, explaining the importance and seeking their explicit buy-in.
   • Use permission-based wording (“Would you be comfortable with that?”) to navigate resistance.
   • Frame the legacy talk as essential for building generational wealth.

4. Handling Pushback and Discomfort ([32:11])

   • Preface tough discussions: directly acknowledge the client may dislike the topic, which paradoxically reduces tension and builds trust.
   • “What I’m about to say to you, you are not going to like and you're probably going to want to kick me out of the office, but I need to bring it up. Are you okay with that?” – Derrick Kinney ([32:13])

Legacy Meetings as a Planning Tool

• Having these values-driven discussions opens the door for related financial planning—like life insurance, distribution rules in trusts, and clarifying how and when heirs should receive assets.
• Citing real-world events or news about celebrity estate failures can normalize the conversation and underscore its importance. ([26:29])

Notable Quotes & Memorable Moments

• On the power of proactive family meetings:
  “It was a moment to change that for this family tree.” – Derrick Kinney ([05:44])
• On legacy prompting self-improvement:
  “They verbalized what they wanted...then began to work on living out a better version of what they wanted to be remembered as.” – Derrick Kinney ([08:12])
• On facilitating without being “too personal”:
  “The key is, you need to have these discussions earlier than you feel you’re comfortable having them.” – Derrick Kinney ([16:16])
• On advisory responsibility:
  “You can’t advise out of fear. Then you’re doing the client a disservice…It’s up to them to say no, but it’s up to us to make sure that they know what options are best for them.” – Derrick Kinney ([29:38])
• On advisor candor:
  “He told his advisor that he would never fire him for telling him something he needs to hear, but he would definitely fire him if he doesn’t.” – Thomas Kopelman referencing Carl Richards ([31:42])

Practical Takeaways for Advisors

• Use emotion and stories to connect estate planning with legacy, not just assets.
• Frame tough conversations with permission-based, disarming language.
• Structure meetings thoughtfully: schedule, invite all stakeholders, and prepare the emotional space.
• Don’t shy away from hard truths—clients respect candor and leadership even when it’s uncomfortable.
• Use current events and client-specific stories as springboards for meaningful discussions.
• Plan for these conversations earlier rather than later in the advisor-client relationship—don’t wait for a health event.
• Reiterate that giving clients what they need (not just what they want to hear) is the essence of advice.

Key Timestamps

• Client Story: Dr. Bob’s Family Meeting – [01:55]–[06:29]
• Developing a Living Legacy – [07:25]–[10:03]
• Facilitation Strategies and Words Matter – [12:01]–[16:16]
• The “Crazy Question” & Raising Difficult Topics – [16:22]–[19:02]
• Setting the Stage, Meetings vs. Visits – [19:40]–[22:26]
• Involving Both Spouses – [22:26]–[25:20]
• Using Current Events to Normalize Estate Conversations – [26:29]
• Advisor Courage & Client Resistance – [29:22]–[32:11]
• The Power of Prefacing Difficult Advice – [32:11]–[33:35]
• Closing, Book & Where to Find Derrick – [34:29]

Episode Tone

Genuine, warm, and practical—focused on turning potentially uncomfortable conversations into opportunities for meaningful connection and responsible planning. Derrick’s storytelling, humility, and humor (“crazy questions”) help make the intimidating subject of estate planning accessible and actionable.