Over decades of work with family business leaders, wealth advisors, and family office professionals, I see the same pattern. Failures result from too much dependence on financial and legal matters. People are emotional. Families are doubly emotional! Right? Think of your family or a client’s emotional mess. Yikes!
Those blind spots can be avoided. Most successful wealth transfers and succession plans occur when some third party expert facilitator supports the process- not the financial and legal factors.
The Missing Piece in Traditional Wealth Planning
While financial and legal expertise IS necessary, they are NOT sufficient. This insight comes from decades of observing what actually happens in family wealth transitions.
Traditional approaches to succession planning typically excel at the easy details that AI can now provide:
Creating tax-efficient structures
Drafting comprehensive legal documents
Developing sophisticated investment strategies
But owners and advisors frequently overlook critical components such as:
The psychological readiness for wealth responsibility – As I’ve written previously, “Next Gen leaders always question if they truly belong, especially if they joined through marriage or face complicated family dynamics. Many Next Gen leaders feel anxiety, loneliness, or self-doubt… and optimism.”
Family communication dynamics – In my experience, even the most brilliantly crafted estate plan fails when the family can’t effectively communicate about difficult topics. Someone is likely to say or do the wrong thing. Unless the process is expertly facilitated.
Leadership development beyond technical knowledge – As noted in my work with books, “Next Gen leaders need more than financial literacy. They need communication skills, emotional intelligence, and the ability to balance innovation with tradition.” Those are dynamic skills. Measurable skills. And very coachable skills!
Thoughtful technological integration – When technology serves human connections instead of replacing them, even the most traditional family members can become enthusiastic supporters.
The Kitchen Table Council Approach
In my article “Making AI Work for Family Businesses,” I described the concept of a “kitchen table council” where multiple generations come together to solve problems collaboratively. This approach exemplifies what effective wealth transition looks like in practice. It is bringing together different perspectives while respecting each voice.
This methodology addresses the full spectrum of challenges facing family enterprises, not just the financial and legal aspects but also the crucial human elements that ultimately determine success or failure. This approach tackles all challenges for family businesses, including financial, legal, and critical human factors impacting their success.
The Four Pillars of Our Legacy & Wealth Leadership Approach
Based on decades of work with family enterprises, our Legacy & Wealth Leadership approach addresses four essential dimensions:
1. Individual Coaching
Next-generation leaders face unique challenges in assuming wealth responsibility. Our coaching helps them develop:
Decision-making frameworks for complex situations
Communication skills for difficult conversations
Emotional intelligence to navigate family dynamics
Personal clarity about their role in the family legacy
Next Gen leaders particularly benefit from structured peer environments where Family and Non-Family Business leaders can share experiences, expert practices, and gain clarity.
2. Team & Family Facilitation
Even brilliant individuals falter without effective team dynamics. Our facilitation services help family enterprises:
Resolve communication breakdowns
Transform destructive conflict into productive dialogue
Align around shared values and vision
Develop governance structures that stand the test of time
In my experience, the power of an interdisciplinary team of advisors cannot be minimized. It’s hard for advisors to ‘sing from the same page’ as if huddled around one piece of paper, but we can do so! And the results can be a beautiful four-part harmony.
3. AI Strategy & Integration
Technology is transforming every industry. Our approach helps family businesses:
Identify the right technological opportunities for their unique situation
For the past year, I’ve focused on how AI can accelerate leadership development. In speeches and product demos clients have practiced difficult communication skills. One client went to www.JITCoach.com and selected role plays and avatars, then practiced 14 times before her next family meeting. The implications are profound for any individual or team leaders who are committed to professional development.
4. Family Office Structuring
For more complex family enterprises, comprehensive wealth structures are essential. Our family solutions help:
Design integrated governance systems
Create communication protocols that strengthen family bonds
Develop decision frameworks that balance innovation with tradition
One of the most influential thinkers alive today is XPrize founder and MD, Peter Diamandis… [who shared] “It is not the strongest of the species that survives, nor the most intelligent that survives. It is the one that is most adaptable to change.” I wrote about those changes for Family Business Consulting in the International best seller,
Why 2025 Demands New Action
The coming months represent a critical period for family enterprises for several reasons:
Technological transformation is accelerating at unprecedented rates
Economic uncertainty accelerates both risks and opportunities
Generational expectations continue to diversify
The pace of wealth transfer is increasing as Baby Boomers age
Families who address these challenges holistically will not only preserve their wealth—they’ll strengthen the bonds that give that wealth meaning.Families who comprehensively tackle these issues will safeguard their wealth and reinforce the relationships that make it valuable.
Join Me for a Virtual Open House: Legacy & Wealth Leadership
If you’re responsible for family wealth—whether as an owner, Next Generation leader, or advisor—I invite you to join me for a virtual event where we’ll explore these topics in depth.
On May 22nd at 11am ET, I’m hosting a short “Legacy & Wealth Leadership” Virtual Open House. You’ll learn:
Why traditional approaches to wealth transition often fall short
Our integrated methodology addressing human dynamics alongside financial structures
Real outcomes in both family harmony and financial returns
As I often tell my clients, “Smart leaders don’t wait for the perfect moment… because they understand there is no perfect moment.” The time to address these critical family wealth challenges is now.
With so much noise surrounding artificial intelligence these days, it’s easy for leaders to feel overwhelmed. Is AI just another tech fad, or is there genuine value beneath the buzzwords? In this conversation, we explore how AI has rapidly evolved from a novelty into an essential business tool and why family businesses are uniquely positioned to benefit from its practical applications.
The Technology Adoption Lifecycle
Think about where Siri and Alexa were just a decade ago. People found them odd and creepy, resisting the idea of being recorded or having their preferences tracked. Fast forward to today, and these AI assistants have become so integrated into our daily lives that we interact with them as if they’re another person in the room.
The technology adoption lifecycle follows a predictable pattern. We’ve moved beyond the innovators and early adopters phase of the 1990s and are now firmly in the early majority phase, where 34% of users are seeking pragmatic use cases. We know AI works, just like Siri and Alexa work. People are using ChatGPT regularly because it’s faster, more reliable, cheaper, and can be confidential.
And who makes the best users? Small business owners and family businesses. They’re agile and adaptive, without the compliance requirements and legal teams that might say “no” in larger organizations. They’re curious about how AI can benefit their businesses.
How Families and Small Businesses Can Cut Through the AI Noise
For leaders feeling overwhelmed by AI hype with countless platforms being thrown at them daily, it’s understandable to feel a sense of AI fatigue. Rather than trying to figure out everything at once, it’s more effective to focus on specific problems you’re facing and then explore how AI might help.
Let’s take sales as an example. A two-year cross-industry study found that sales teams using AI-powered training sold 24% more than teams that didn’t. Most companies would go to extraordinary lengths for even an 8% increase in revenue. This represents a simple, cost-effective tool that eliminates the risk of salespeople learning on the job with real clients. They can safely master all personas, objections, and value propositions before stepping into the field.
Overcoming Fear and Resistance to AI Adoption
Fear often defines us. Whether it’s fear of geopolitical decisions, new technologies, or change in general, we naturally resist what we don’t understand. But when evaluating any new technology, we should consider three key factors: Is it efficient? Is it effective? And what are the outcomes?
Every specialized profession is facing disruption right now:
Attorneys may resist robo-advisors
Wealth investors might shy away from AI-driven investment strategies
Organizational employees might fear automation replacing human roles
Yet every industry will be affected by AI in direct ways within the next 5-10 years. So why not overcome that resistance and learn how to implement AI in your business?
When faced with change, we typically respond in one of three ways: freeze, flight, or fight. We can freeze like a rabbit in the forest and try to ignore AI’s inevitable adoption. We can run away from it. Or we can fight—not against AI, but alongside it, wrestling with its potential until we master it.
If 45% of business owners are already using AI and your competitors are among them, the question becomes: why wouldn’t you use it now, especially if you had a secure way to do so in a closed system?
The Human Element: Why a Hybrid Approach to AI Coaching Matters
While AI platforms like Claude can help draft emails or prepare for difficult conversations, they lack the human dimension that addresses the emotional challenges we face. What if you could combine AI with human coaching to improve your ability to handle difficult and sensitive conversations?
Imagine practicing a difficult conversation with an AI avatar programmed to respond like the actual person you’ll be speaking with. As you rehearse multiple times, your confidence grows. Then, when you discuss your progress with a human coach who can address your internal struggles and provide personalized feedback, you’re getting the best of both worlds.
This hybrid coaching approach is three-dimensional rather than flat. The AI component provides consistent practice opportunities and immediate feedback, while the human coach adds depth, emotional intelligence, and personalized guidance that helps the learning stick.
Communication capability makes a tremendous difference in business success. Strong communication skills in leaders allows them to put out “people fires,” handle employee conflicts, reduce turnover, and free up business owners to focus on leadership and maintain work-life balance.
Effective management hinges on the ability to have productive conversations around delegation, feedback, accountability, hiring, termination, and performance improvement. Developing these skills traditionally required significant time investment from the manager and trainee. Now, with AI-assisted practice, managers can rapidly develop these crucial skills through repeated role-plays and targeted feedback.
Another study showed that this approach improved management capability by 24%. For small business owners struggling with operational challenges, this represents a fast, cost-effective way to make significant improvements.
Getting Started with AI
For those excited about AI and already using various platforms, the key is to just begin. Experiment and dabble. Pick any platform—ChatGPT, Perplexity, Claude, Poe—and start using it. The paid options ($20/month) generally provide better results.
If you have digital content—books, research, business documents—you can upload them to create a personalized AI that speaks your language. And by selecting privacy options that prevent sharing your content with large language models, you’ve created a confidential AI system for your organization that nobody else can access.
Many businesses are already using these tools for business protocols, operational processes, manufacturing, and marketing analyses. The question isn’t whether to adopt AI, but why wait any longer?
The future of professional development isn’t just AI or just human coaching—it’s both working together to accelerate your growth and success.
This blog post was adapted from a conversation with Doug Gray and Israel Hillegeist on practical AI applications for small businesses.
Interested in learning more about AI Coaching for Communication? Join the next edition of the Next Gen Leadership Series. https://www.nextgenpeergroups.com/the-next-gen-leadership-series
We wrote this conversation based on a short video recording… edited by AI tools that summarized us. Then edited by our marketing manager, Erin, who is a real person. We imagine that any leader, in any sector, can learn how to use AI in their business immediately. Reply or comment or connect?…. see www.JITCoach.com or schedule a demo
Artificial intelligence dominates headlines with promises of revolutionary change, so it’s easy to feel overwhelmed by the noise. But beneath the hype and buzzwords lies tremendous value that can be applied immediately—particularly for family business leaders, Next Gens and smaller organizations.
Cutting Through the AI Noise
There’s a lot of “hoo-ha” around artificial intelligence today. Open any business publication—Harvard Business Review, McKinsey reports, VentureBeat, or Forbes—and you’ll find endless articles about AI’s utility, examples, and trends. Terms like “predictive analytics” get tossed around without clear definitions. Can we truly predict the next word in a sentence or the next market opportunity? There are tools like Lex Machina and Bloomberg Law that can forecast divorce or succession risk. But should they do so? The ethical clarity isn’t always there.
What we call “artificial human intelligence” are essentially algorithms—compilations designed to anticipate the next word. You’ve experienced this already: when you type “How do I…” into a Google browser, it fills in the likely next words, based on your search history. This predictive capability has evolved from simple sentence search completion to sophisticated tools like Microsoft’s Copilot that can generate content, edit documents, and create personalized interactions. AI learns from itself, which is why the default browser for Google has recently been replaced by Gemini.
The Rise of Customized AI
One of the most powerful developments is the ability to create customized AI systems. I’ve built what some call a “closed chat GPT”—an AI trained on my books, dissertation, research papers, blog posts, and website content. I call it “Gray Matters” and share it with my clients. When asked, “How would Doug respond to this situation?” it provides evidence-based answers drawn from that data set. Crucially, you can configure these closed systems to maintain confidentiality, which prevents your data from being shared with large language models.
Small business leaders can leverage this same technology. If you need to maintain client confidentiality for legal reasons but want to provide unique value to those clients, a closed AI system offers a perfect solution. This fact explains why there are so many chatbots on company websites—they’re cost-efficient and can provide consistent service 24/7. Do you need to invest in Schwab or Fidelity or Vanguard? Then you need to interact with bots before humans.
Digital Trust and Consumer Adaptation
Remember when Amazon first introduced Prime? Many doubted that package would succeed. Now one-click purchasing and “people like you bought” suggestions have become standard AI tools. These weren’t implemented randomly—they were based on extensive data analysis showing that buyers of one product were likely to purchase related items.
This example reflects a broader trend: we have developed increased digital trust in AI tools. Think about how you interact with Siri or Alexa—as if there’s another person in the room. These AI assistants weren’t part of our lives a decade ago, yet now they’ve become integral to our daily routines. Our expectations around AI are also shifting—we expect it to be personalized, always available, and worthy of our digital trust.
Accelerating Leadership Development
For the past year, I’ve focused on how AI can accelerate leadership development. The implications are profound for any individual or team committed to professional development. We can now provide 24/7 utility to confidential resources and interactive learning opportunities using AI avatars based on customized role-plays and scenarios.
Imagine clicking on ChatGPT repeatedly to gain insight into difficult topics: How do I deal with anxiety? How do I sleep better? How do I have a difficult conversation with a family member who’s resistant to dialogue? Now, these are skills that can be developed through deliberate practice.
Years ago, when I asked Google, “Can you be my executive coach?” it said “Not at this time.” Today, any AI platform—whether it’s ChatGPT, Claude, Grok, Poe, or another—will happily take on that role.
Our Hybrid Coaching Solution
AI can re-design executive coaching, leadership consulting, and transform your career. Imagine using hybrid coaching that combines AI practice with human expertise. Let me give you some examples.
A client named George wanted to develop better communication skills but didn’t want to ask his manager for help. Using our AI platform, George practiced difficult conversations repeatedly in a confidential environment. Then, when we meet for our 1:1 executive coaching session, George can share his screen and show me his AI interactions. I can provide feedback not just on the content of his responses but on his approach to learning.
This hybrid model works across professions. Imagine you’re a lawyer with clients who need to discuss succession planning, or a family wealth advisor helping clients prepare for difficult conversations with the next generation. These discussions require skills that many people haven’t developed. Behavioral feedback can provide better analysis and coaching suggestions than humans. When we practice new skills with AI, my clients can find the right words and approaches before having those crucial real-world conversations.
B2C and B2B Applications
I’ve developed two models for implementing hybrid consulting:
B2C (Business to Consumer): Individuals can access a platform to practice scenarios like dealing with anxiety, burnout, difficult family members, or deeper questions about purpose and faith. For about $100 monthly ($1,200 annually), users get unlimited access to AI-assisted practice scenarios. That investment often delivers more lasting value than a couple of traditional coaching sessions at the same investment level. See www.JITCoach.com or ask for a demo.
B2B (Business to Business): Teams and organizations can implement AI-assisted consulting to accelerate skill development. The data is compelling—sales teams using these approaches have shown a 24% increase in sales performance and 97% improvements in training retention. Compared to traditional online training programs that often show minimal results, this AI-assisted consulting represents a breakthrough. See www.Action-Learning.com or ask for a demo.
The Bottom Line
Artificial intelligence has been evolving since 1995. Now we have reached a point where it’s more consumer-friendly and accessible than ever. Just as you talk to Siri or use ChatGPT, you can now use AI-assisted consulting tools to accelerate your skill development, improve communication, and achieve outcomes faster, more effectively, and more affordably.
We will interact with AI-driven cars and live in an AI-enhanced world. Why wouldn’t we apply these same technologies to leadership development and executive coaching?
Want to learn more about implementing AI in your leadership development? Contact Doug at doug@action-learning.com or visit action-learning.com to schedule a demo.
Many people ask me this question. So you are not alone. In fact, self-leadership is an ancient subject turned into a multi-billion dollar industry. It is MUCH harder to lead my self than it is to lead others. And it requires daily deliberate practice for me to lead my self.
My purpose in life is to teach others how to be better leaders. I know what works. Hopefully the following two steps will be useful to you.
There are two ways to lead your self:
1. self awareness
2. self care
Self awareness requires core skills such as openness, self appraisal, clarity, self esteem. There is a massive amount of research in psychology and organizational development on the subject of self awareness. There are countless religions and faiths and daily practices on the subject of self awareness. Amid these conflicting and spurious theories there is a need for clarity. We use assessments to provide data. There are over 15,000 validated assessments. We can provide assessments for any individual behavior or competency imaginable. Evidence-based consulting is mandatory in any profession, from law to healthcare to psychology.
A key coaching question is “What assessments do I need to increase my self awareness?’
Self care requires core skills such as expression, sustainability, resourcefulness, action. Consider the fact that humans now have more digital information available than EVER in the history of mankind. We now KNOW what we should do. However, we do not always DO what we should do. Imagine a grandmotherly person. She towers over you with an apron and shakes a wooden spoon… as she tells you what you should do. That image of a wise, older person may help you.
A key coaching question is “How can I take care of myself today?”
One more point. There is a myth that leadership is a personal act. By definition, the word “leadership” means influence at two levels: on my self and others. The goal of self leadership is not to attain some mystical state in isolation on a mountain. Humans are defined by relationships. No one develops as a leader when living in isolation. And too many people spend hours alone, writing in journals, or focusing on their weaknesses. When Maslow described self actualization it was not thought to be a resting place. The goal is to improve the quality of relationships with others. Leadership is both a personal act and a team act. We adopt evidence-based research in positive psychology because it works. We want YOU to flourish.
The goal of self leadership is to have a greater relationships with my self and others.
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