112: Navigating Family Wealth Transfers: Emotional Intelligence and Effective Communication with Jill and Sean Maher

“We’re talking about giving space to practice. Not only practice the relationships but also practice managing money.” -Sean Maher

 

Most people plan their estate down to the last dollar, but forget to prepare for the emotional fallout that almost always comes from a lack of proper communication between family members.

 

Our hosts, Stephanie McCullough and Kevin Gaines, sit down with husband and wife team Sean and Jill Maher to talk about their book The Greatest Gift: 9 Principles for the Transfer of Your Legacy Along with Your Wealth, which journeys into the emotional side of passing down wealth and family legacy.

 

The idea for the book came after Sean, a financial advisor, saw a well-planned inheritance fall apart when a family started fighting after their parents passed. He brought the issue home to Jill, a mental health counselor, who pointed out that what he was really seeing wasn’t a planning problem—it was grief. Together, they’ve come up with nine key principles that help families avoid drama and stay connected regarding inheritance.

 

The big takeaway? It’s not just about the money. No matter how much (or little) you're passing on, what matters most is communication, shared values, and emotional safety.

 

Jill and Sean suggest families start having small, low-pressure meetings early, while everyone’s still around to talk things through. It’s about creating space for honest conversations, building trust, and setting expectations. Their advice blends practical planning with emotional wisdom, encouraging people to treat legacy as a relationship, not just a transaction.

 

At the heart of it all, their message is simple: don’t avoid the tough conversations—have them, and carry them out with love.

 

Key Topics:

• Why Sean and Jill Wrote The Greatest Gift (03:52)
• “You’re Passing on Not Just Money, But Also Legacy” (05:23)
• How to Set Up and Facilitate the Inheritance Conversation with a Family (09:59)
• Setting Expectations Upfront to Nip Objections in the Bud (20:55)
• Why Sharing Your Story is So Critical (27:54)
• Nurturing Independence (33:26)
• Creating a Safe Environment for Your Children (43:23)

 

Resources:

• The Greatest Gift Book USE COUPON CODE: takebackretirement for $5 off and free shipping!

 

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You can find the transcript and more information about this episode at www.takebackretirement.com.

 

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