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The Human + AI Equation: Practical Applications for Families and Small Businesses

by | Apr 3, 2025 | Business, Consulting, family, Family Wealth, Featured, Leadership, Managers, money, organizational leadership, 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

AI Adoption in Family Business: Balancing Trust and Tech

by | Apr 1, 2025 | Consulting, Leadership, 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

  1. 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. 
  2. 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.
  3. 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.
  4. 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. 
  5. 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.
  6. 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.

  1. 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

  1. 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.
  2. 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.
  3. 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.
  4. 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.

What is the core of every physician-patient relationship?

by | Jun 14, 2015 | change, Coaching, healthcare, Leadership, Managers, physicians

The core of physician-patient relationships is trust.

But what do you know about your physician’s values regarding end of life decisions, or women’s reproductive choice?  What do you know about the treatment and care suggested by your physician, who may be eligible for a $5,000 referral fee or $2,500 volume price incentive?

Leana Wen, MD, is a Rhodes Scholar and author of “When Doctors Don’t Listen.”  Her TED talk, called “What your doctor won’t disclose,” has been viewed by over 1.3 million people.

Her story includes role models from her childhood in China, to a campaign called “Who’s my doctor?” designed to encourage doctors to share their values and be more transparent with their patients.

She states, “we need to change the paradigm of medicine from sickness and fear to openness and healing.“

blog from Seth Godin on Unemployment, Entrepreneurship, and the future of business

by | Mar 27, 2013 | book review, change, Coaching, Employment, money, Resources, strengths

My brother sent me this blog article today, from Seth Godin, best-selling author and marketing guru… it provoked me.  What do you think?

Toward zero unemployment

A dozen generations ago, there was no unemployment, largely because there were no real jobs to speak of. Before the industrial revolution, the thought that you’d leave your home and go to an office or a factory was, of course, bizarre.

What happens now that the industrial age is ending? As the final days of the industrial age roll around, we are seeing the core assets of the economy replaced by something new. Actually, it’s something old, something handmade, but this time, on a huge scale.

The industrial age was about scarcity. Everything that built our culture, improved our productivity, and defined our lives involved the chasing of scarce items.

On the other hand, the connection economy, our economy, the economy of the foreseeable future, embraces abundance. No, we don’t have an endless supply of the resources we used to trade and covet. No, we certainly don’t have a surplus of time, either. But we do have an abundance of choice, an abundance of connection, and an abundance of access to knowledge.

We know more people, have access to more resources, and can leverage our skills more quickly and at a higher level than ever before.

This abundance leads to two races. The race to the bottom is the Internet-fueled challenge to lower prices, find cheaper labor, and deliver more for less.

The other race is the race to the top: the opportunity to be the one they can’t live without, to be the linchpin we would miss if he didn’t show up. The race to the top focuses on delivering more for more. It embraces the weird passions of those with the resources to make choices, and it rewards originality, remarkability, and art.

The connection economy continues to gain traction because connections scale, information begets more information, and influence accrues to those who create this abundance. As connections scale, these connections paradoxically make it easier for others to connect as well, because anyone with talent or passion can leverage the networks created by connection to increase her impact. The connection economy doesn’t create jobs where we get picked and then get paid; the connection economy builds opportunities for us to connect, and then demands that we pick ourselves.

Just as the phone network becomes more valuable when more phones are connected (scarcity is the enemy of value in a network), the connection economy becomes more valuable as we scale it.

Friends bring us more friends. A reputation brings us a chance to build a better reputation. Access to information encourages us to seek ever more information. The connections in our life multiply and increase in value. Our stuff, on the other hand,  becomes less valuable over time.

… [this riff is inspired by my new book…]

Successful organizations have realized that they are no longer in the business of coining slogans, running catchy ads, and optimizing their supply chains to cut costs.

And freelancers and soloists have discovered that doing a good job for a fair price is no longer sufficient to guarantee success. Good work is easier to find than ever before.

What matters now:

  • Trust
  • Permission
  • Remarkability
  • Leadership
  • Stories that spread
  • Humanity: connection, compassion, and humility

All six of these are the result of successful work by humans who refuse to follow industrial-age  rules. These assets aren’t generated by external strategies and MBAs and positioning memos. These are the results of internal struggle, of brave decisions without a map and the willingness to allow others to live with dignity.

They are about standing out, not fitting in, about inventing, not duplicating.

TRUST AND PERMISSION: In a marketplace that’s open to just about anyone, the only people we hear are the people we choose to hear. Media is cheap, sure, but attention is filtered, and it’s virtually impossible to be heard unless the consumer gives us the ability to be heard. The more valuable someone’s attention is, the harder it is to earn.

And who gets heard?

Why would someone listen to the prankster or the shyster or the huckster? No, we choose to listen to those we trust. We do business with and donate to those who have earned our attention. We seek out people who tell us stories that resonate, we listen to those stories, and we engage with those people or businesses that delight or reassure or surprise in a positive way.

And all of those behaviors are the acts of people, not machines. We embrace the humanity in those around us, particularly as the rest of the world appears to become less human and more cold. Who will you miss? That is who you are listening to .

REMARKABILITY: The same bias toward humanity and connection exists in the way we choose which ideas we’ll share with our friends and colleagues. No one talks about the boring, the predictable, or the safe. We don’t risk interactions in order to spread the word about something obvious or trite.

The remarkable is almost always new and untested, fresh and risky.

LEADERSHIP: Management is almost diametrically opposed to leadership. Management is about generating yesterday’s results, but a little faster or a little more cheaply. We know how to manage the world—we relentlessly seek to cut costs and to limit variation, while we exalt obedience.

Leadership, though, is a whole other game. Leadership puts the leader on the line. No manual, no rule book, no überleader to point the finger at when things go wrong. If you ask someone for the rule  book on how to lead, you’re secretly wishing to be a manager.

Leaders are vulnerable, not controlling, and they are racing to the top, taking us to a new place, not to the place of cheap, fast, compliant safety.

STORIES THAT SPREAD: The next asset that makes the new economy work is the story that spreads. Before the revolution, in a world of limited choice, shelf space mattered a great deal. You could buy your way onto the store shelf, or you could be the only one on the ballot, or you could use a connection to get your résumé in front of the hiring guy. In a world of abundant choice, though, none of these tactics is effective. The chooser has too many alternatives, there’s too much clutter, and the scarce resources are attention and trust, not shelf space. This situation is tough for many, because attention and trust must be earned, not acquired.

More difficult still is the magic of the story that resonates. After trust is earned and your work is seen, only a fraction of it is magical enough to be worth spreading. Again, this magic is the work of the human artist, not the corporate machine. We’re no longer interested in average stuff for average people.

HUMANITY: We don’t worship industrial the way we used to. We seek out human originality and caring instead. When price and availability are no longer sufficient advantages (because everything is available and the price is no longer news), then what we are drawn to is the vulnerability and transparency that bring us together, that turn the “other” into one of us.

For a long time to come the masses will still clamor for cheap and obvious and reliable. But the people you seek to lead, the people who are helping to define the next thing and the interesting frontier, these people want your humanity, not your discounts.

All of these assets, rolled into one, provide the foundation for the change maker of the future. And that individual (or the team that person leads) has no choice but to build these assets with novelty, with a fresh approach to an old problem, with a human touch that is worth talking about.

I can’t wait until we return to zero percent unemployment, to a time when people with something to contribute (everyone)  pick themselves instead of waiting for a bureaucrat’s permission to do important work.