Why do we put off the conversations that matter most? Whether it's a tough call with a business partner, a long-overdue chat with a family member, or feedback you've been sitting on for weeks, avoidance has a cost — small misunderstandings turn into resentment, and resentment turns into broken relationships and lost opportunities.

In this episode, we sit down with Dr. Keita Demming — award-winning educator, coach, and Director of Development & Innovation at The Covenant Group — to talk about how to stop dodging hard conversations and start having them sooner, with more clarity and less damage.

In this conversation, Keita shares:

• Why leadership is fundamentally about noticing what others ignore — and saying it out loud
• The ISI Model (Indisputable, Sense-making, Interpretation) and how it keeps difficult conversations grounded in facts instead of feelings
• How to separate what actually happened from the story you're telling yourself about it
• Practical techniques for family enterprises, where personal ties and professional roles collide
• Why collaboration — not winning — is the real goal of any hard conversation
• How to set up a conversation so the other person can actually hear you

Learn More about Keita 

• 🌐 Keita's website: keitademming.com
• 🏢 The Covenant Group: covenantgroup.com
• 📘 Buy Strategy to Action: Run Your Business Without It Running You: 
  • Amazon (US)
  • Barnes & Noble
  • Page Two (publisher)

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

We keep seeing the "paradox of choice" show up in our coaching work with Rising Gen clients from affluent families. The theme has re-emerged with a vengeance: young adults in their 20s who have every door open to them, and yet can't seem to walk through any of them.

Thats why this week we're unpacking  why access and abundance can actually stunt decision-making, and why high-achieving kids who thrived with a clear rubric in school can become completely disoriented when the rubric disappears.

This Week We Are Discussing

-Why Rising Gen clients from affluent families keep getting stuck
-The paradox of choice — and how the jam study explains it
-Why shame and fear make it harder to ask for help
-A practical framework for building your own rubric and getting unstuck
-Why the first decision at 25 doesn't have to be the right decision — just a decision

Shout Out To The Following Books

The Defining Decade by Meg Jay
Designing Your Life by Bill Burnett & Dave Evans

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

In this episode, Dr.Dan McDonald (human factors psychologist with military and government experience) breaks down how trust, leadership, and culture actually determine whether family wealth lasts or falls apart.

We get into:

-Why “soft skills” are actually hard ROI drivers
-How to use simple frameworks (like logic models) to measure what matters
-What families can learn from the military about leadership and succession
-How AI, tech, and generational shifts are changing everything

Follow Dr.Dan:https://www.linkedin.com/in/dr-daniel-p-mcdonald/ 
Performance Absolute: https://performanceabsolute.com/

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

This week we're talking about one of the toughest conversations of all - how to ensure a meaningful peaceful death of a loved one.  We're joined by Robin Norcross (Purposeful Passages) who guides us through proven strategies to normalize death talk, helping you can prepare for the inevitable with dignity and love.

We Discuss
-The surprising truth about why most people fear talking about death and how to overcome it
-A simple framework to start meaningful conversations with family about end-of-life wishes
-Why planning ahead leads to less pain, suffering, and conflict when the time comes
-The impact of the coming “great transfer of wealth” on caregiving and legal systems
-How embracing death as a natural part of life transforms our relationships and legacy

Follow Robin: https://www.linkedin.com/in/torri-hawley
Purposeful Passages: https://www.ourpurposefulpassages.com/meet-robin

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

This week we're joined by Torri Hawley from Tamarind learning to discuss the often misunderstood role of a trustee. We're chatting explore the responsibilities of trustees, the importance of education for beneficiaries, and the dynamics of trustee-beneficiary relationships. 

Follow Torri: https://www.linkedin.com/in/torri-hawley
Tamarind Learning: https://tamarindlearning.com/

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

This week we answer the difficult question that families very often have to answer "Are We Rich?"

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

Happy New Year! We're kicking 2026 off by discussing  the do's and don'ts of coaching calls, the importance of preparation, and how to take ownership of your growth journey. 

Tune in for insights that will transform your approach to personal development. 

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

In our first holiday themed episode of The Family Wealth Edge, Sara E. Miller joins us for a pop culture discussion on the underlying themes in holiday movies, particularly Hallmark and Lifetime movies. 

Follow Sara: https://www.linkedin.com/in/miller-sara-e/

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

Today Kristen Heaney and Vincent Valeri, MBM, FEA are discussing the best and worst things that can happen in family meetings.

Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/

Follow Vincent: https://www.linkedin.com/in/vincentvaleri/

Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge