by Doug Gray | Apr 3, 2025 | Uncategorized
March 11, 2025
Adapted from a conversation with Doug Gray, PhD and Israel (Jon) Hillegeist on cutting through AI noise and finding real solutions
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.
[You can learn more about this hybrid program here.]
Real-World Applications
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
Doug Gray, PhD AuthorFamily Wealth Advisor | Business Change Management | Organizational Leadership | Assess Next Gen | Succession Planning | Executive Coaching
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
by Doug Gray | Apr 2, 2025 | Uncategorized
Let’s get real…
By Doug Gray, PhD
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.
by Doug Gray | Apr 1, 2025 | Uncategorized
Summary: In a time of rapid AI acceleration, family business leaders must balance innovation with intergenerational trust. Here are six key risks—from data privacy to ethical forecasting—and practical AI applications already transforming client engagement. Drawing on examples from the AFHE Spring Conference last week, and my client case studies. AI must support, not replace, human relationships. For family advisors, innovation is no longer optional—it’s expected.
Artificial intelligence (AI) dominates many conversations. For some people, AI is a catalyst for innovation. For others, AI is a threat cloaked in code.
The Technology Adoption Curve model describes how tools such as AI have been adopted by Innovators (2.5%), Early Adopters (13.5%), Early Majority (34%), and Late Majority (34%). That model begs my question: How can we measure our rate of AI adoption in Family Business?
Many younger people are more digitally trusting than elders and owners. Some multi-family offices, RIAs, and consulting firms are designed to serve Millennial and Gen Z inheritors. Advisors know that family business leaders must not only preserve capital—they must also preserve trust across generations.
At the recent Attorneys for Family-Held Enterprises (AFHE) Spring Conference, I asked advisors to rate their own AI usage and fears on a scale from 1 to 10. The responses painted a familiar picture of curiosity mixed with concern. One advisor quipped, “I’ve used ChatGPT to write emails, but I still don’t trust it with anything sensitive.” I shared how to create a customized GPT that protects sensitive client information and does not share data with large language models (LLMs). Another enthusiastic advisor described AI adoption as “table stakes” for maintaining relationships with Next-Gen clients, who expect personalized planning, 24/7 access, and digital transparency. He is worried about retaining AUM from younger owners.
That tension—between confidentiality and innovation—describes the risks, challenges and need for change. Here are some practical applications based on my AI consulting solutions that readers can implement.
Six Risks for Family Business Leaders
- Data Privacy & Security: All leaders must access and protect sensitive financial and family data. Data breaches aren’t just costly—they’re unacceptable. Every trusted advisor in every business sector knows that our fiduciary demands require closed access, digital firewalls, and the most robust multi-factor authentication security protocols. I have heard stories of repeated multi-million-dollar attacks. Countless Family Offices and business leaders are targets for cybercriminals because they have access to wealth. We also know that inconsistent human behavior is a poor substitute for those AI-driven criminals.
- Over-Reliance: Replacing human emotional intelligence with algorithms may feel good because of the dopamine surge, but it erodes relational trust. I’ve heard clients say, “I interact more with my GPT than with people!” Psychologists and clinicians have studied the impact of digital addiction for decades now. We know that over-reliance on digital resources is a factor in anxiety, depression, sleep problems, obesity, neck and eye strain and memory loss. In short, AI is not a substitute for positive human interactions.
- Ethical Predictive Use: There are tools like Lex Machina and Bloomberg Law that can forecast divorce or succession risk. But should they? AI-driven actuaries and healthcare data sets can now predict lifespan and health risks. But should they? There is no universal acceptance of the ethical boundaries that can be recommended to protect individual rights. There is no acceptance that any government, tech company, or international community has defined ethical uses of AI. The implications for insurance companies, health care providers, philanthropy and estate planning are rarely discussed. We need to develop ethical boundaries for AI use.
- Regulatory Uncertainty: As AI applications accelerate, the tools always get faster, cheaper and more accurate. Some regulatory agencies, including the SEC and FINRA, have developed guidelines. But the bottom line is that AI applications are designed to learn from themselves, to improve efficiency in microseconds. By their design “black-box AI tools” are secret. They lack transparency and defy regulatory compliance. We need to develop regulatory AI guidelines that resist bias and protect individual confidentiality.
- Resistance to Change: In response to countless threats, humans have always adapted to evolve slowly. We always protect our assets. Some are inclined to say, “Yes, of course I embrace change. You go first.” Many solo advisors admit lacking the bandwidth to vet new AI tools or automate workflows. One of my clients said, “I know I need AI scanning tools like Optical Character Recognition (OCR) someday- but certainly not during tax season!” Thankfully, anyone can now use AI to design business templates for any possible change.
- Talent Gaps: We all make mistakes when we “don’t know what we don’t know.” Did you know that there are some key competencies that are uniquely human and will never be replaced by AI? Those competencies include resilience, humility, empathy, curiosity and learning agility. When we identify how to assess and develop those competencies, then we redefine career and talent gaps. Without doubt, AI is here to stay. How we use AI will redesign all family business consulting.
Consider the following examples.
Using AI to Re-Design Family Business Consulting.
- Adopt AI-tools that scaffold learning, like micro-coaching sessions, or simulations. One example is my AI-assisted communication coaching platform that provides confidential analysis and feedback using customized role plays. Imagine selecting a role play like “sibling conflict” or “succession planning.” Then select an avatar based on the interactions you anticipate or skills you need to develop (e.g., blunt, skeptical, friendly, etc). Then record your interactive learning. Study the confidential analysis, feedback, and transcript. Practice again and again. We know that deliberate mastery accelerates skill development. When I did a demo with an audience last week, they said, “This is incredible technology, and gets at communication– the heart of all conflict problems.” Those individual, recorded sessions are GPDR and SOC2 compliant, and have been embraced by Korn Ferry, Spencer Stuart and Google. Any presentation, interview or recoded content can be uploaded for analysis and feedback. Imagine improving your communication skills with immediate feedback before meeting with a demanding sales manager. One tech company found a 24% increase in sales when they used this platform. Another large company trained 15,000 people in weeks, with a 97% training completion rate and high engagement scores. See www.JITCoach.com or ask for a demo.
- Use AI to record meetings summaries, create action plans and task lists. With permission from all participants, many host platforms (e.g., Zoom and Microsoft Teams) can provide summaries for any number of participants. I have hosted webinars where AI Summaries (e.g., Otter and Fireflies) outnumber the number of human participants. The value for busy professionals is access to the webinar content when they may be double-or-triple-booked. The value to me as the webinar host is high quality, consistent distribution of my key points within minutes to those who want that summary.
- Use AI summaries as a personal development tool. Self-coaching with “mirror, mirror on the wall” is not useful. However, recording a private session on your zoom screen is an opportunity for assessment and development. That recording can be stored on a password-protected thumb drive for security. If uploaded into a private YouTube link, you can then click a button and see your transcript. Any GPT can then edit your text and suggest changes. If you want to be more assertive, the AI will provide a revised text. If you want to be more emotionally vulnerable, AI will provide another revised text. We have more access to behavioral feedback than ever before in human history.
- 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.
- Use multiple AI tools to develop expertise. If I ask Chat GPT “How can I accelerate succession planning for a family business?” It will provide pages of information. If I’m confused, I can always ask “Tell me more…” and it will do so. But the quality of my prompt determines the quality of the response. So, if I copy that first response and paste it into Grok I can then ask, “Analyze this document and suggest improvements.” Then I can take the second response and paste it into Gemini to ask, “What am I missing?” and now I have responses from three data sources. Like asking three colleague or three interns for their perspectives, the value of that final result is 3x better. Consultants have always sought opinions from multiple sources. When you add AI to your research the quality may be surprisingly good.
Case in Point: A Next-Gen Shift
Consider a second-generation family CEO in Nashville, TN, who introduced AI-generated financial dashboards to quarterly family meetings. The elder cousins were initially skeptical. They embraced the dashboards—not because of the tech, but because the founder emphasized how these tools would reduce conflict and increase transparency.
The result? Fewer side meetings, more collaborative planning, and, surprisingly, more laughter around the kitchen table and the board room table.
Takeaways for Family Business Leaders
- Start small: Try AI-generated summaries (e.g., from Zoom or Microsoft Teams, with client permission). Edit them and share discretely. Select an AI tool (e.g., Chat GPT, Claude, Gemini, Grok) for searches. Save it in your task bar so that you use it frequently. Edit results from one AI tool to another, then select the tool that best serves your needs.
- Engage your team: Create internal cross-functional task forces with IT, compliance, and client experience leaders. Focus on solving client problems, rather than cool new solutions.
- Educate clients: Share how AI supports (not replaces) your professional counsel. Solicit feedback on topics or services required by your clients. Automate those services and continue soliciting market feedback.
- Ask the trust question: “How does this AI tool deepen our trusting relationship?” Clients stop engaging advisors when they perceive limited value. AI tools can add significant value when used with care.
Final Word: Innovation is Now an Expectation
As fiduciaries, educators, and ethical leaders, family business advisors must balance technical advancement with emotional insight. Clients trust advisors who care—more than those who depend on AI.
Doug Gray, PhD is the CEO of Action Learning Associates, author of The Success Playbook for Next Gen Family Business Leaders (2024) and creator of JITCoach.com. He specializes in leadership development, AI coaching, and succession planning in family-owned enterprises.
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