by Doug Gray | 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
by Doug Gray | Dec 13, 2024 | change, Financial Professionals, Leadership, Managers, organizational leadership, positive psychology, strengths, Success, talent
The Future of Family Offices: Why Multidisciplinary Teams Are Essential
The goal of every family office is the same- to serve the financial and capital needs of current and future generations. However, the process is changing.
We will always require attorneys and wealth advisors to “stay in their swim lanes” and practice compliance. That will never change. Those silos are necessary, but NOT sufficient. Today, cross functional teams of interdisciplinary advisors are collaborating and providing external expertise.
Recently I was asked to create video recordings for a multi-family office (MFO) with over $1B in assets under management. They wanted me to share succession planning advice with their 80+ clients. Last week I talked with my new friend, Charmaine Tang, CEO of Orca Americas, about the need for people and technology to model innovation for family offices. Also last week I invited Brannon Fisher, a MFO partner, to share advice with our Next Gen Peer Group leaders when we met in Denver. Minutes ago I spoke with Bradley Franc, CEO of Succession Strategies, who said, “We don’t do what you do. We should partner.”
Notice the pattern?
We all have such meetings, because we all serve the current and future needs of our clients.
I can only imagine that such collaboration will accelerate. There is a growing trend toward building multidisciplinary teams within large family offices. Those internal teams may include specialists from various fields together to collaborate and provide comprehensive advice. Naturally, each advisor brings unique legal, financial, or relational expertise. Every smaller Family Office needs to do the same. They need to develop external teams of expert advisors. The power of multidisciplinary collaboration lies in our ability to address the full complexity of family dynamics and wealth management.
Wealth advisors, thankfully, are focused on maximizing assets for long-term gain. Attorneys and insurance advisors focus on protecting assets and minimizing risk, thankfully! Both roles are critical and are NOT sufficient for Next Gen leaders who expect more transparency, digital access, and opportunities to learn.
Family Offices, like any social organization, need to evolve. Every aspect of the family’s wealth or legacy deserves expert advice.
Navigating Intergenerational Conversations
Consider a typical family office meeting: the Elder Generation is planning for retirement and succession, while the Next Generation is learning about investments and long-term financial planning. In the middle, a team of advisors—legal, economic, and often behavioral psychologists (like me) —helps facilitate the conversation.
These discussions may be delicate. The Elder Generation needs to learn to bite their tongues. They need to encourage the Next Generation to ask questions about access to funds, investment strategies, and their personal goals.
For younger family members, these meetings present an opportunity to learn about critical topics like compounding interest, wealth distribution, and long-term planning. I’ve been facilitating a series of family meetings with three Elders, five Next Gens, and three wealth advisors from Northern Trust. By the end of the last session, the Elders were beaming with satisfaction. A multidisciplinary team ensures that these meetings are not just about financial details but about fostering open, constructive dialogue across generations. Advisors from different fields can help ensure that the right questions are being asked and that all voices are heard.
The Expanding Role of the Family Office
Family offices have historically focused on wealth management—handling investment portfolios, estate planning, and tax strategies. But the role of the family office is evolving faster than ever. Many family offices are expanding toward a more comprehensive model that addresses both financial and Family Capital.
The Family Capital Model includes five key areas:
- Health and well-being
- Family governance and decision-making
- Succession planning and education for the next generation
- Family dynamics and interpersonal relationships
- Risk management, both financial and relational
This expansion reflects a broader understanding that to preserve a family’s legacy, the focus must be on the whole family, not just its financial assets. How do Family Office leaders support that broad need? With timing and expertise.
The Importance of Multidisciplinary Collaboration
Timing matters. Bringing in the right expertise at the right time is critical for any family office. A well-rounded team of advisors can ensure that a family’s needs—whether related to wealth, legal matters, or family dynamics—are met efficiently and effectively. When a Family Office relies solely on financial experts, it risks overlooking other vital family legacy elements. A multidisciplinary team mitigates this risk by ensuring that all aspects of the family’s life and legacy are considered in decision-making processes. Quarterly meetings work well. An annual cadence of ownership meetings is a minimal requirement.
Expertise matters. Advisors from different disciplines often approach problems from unique perspectives. After years of formal schooling, credentialing, and serving similar clients, those perspectives are reinforced and they bias every advisor. Thankfully! Think of any trigger event, like the sale of an asset or death of an Elder. Financial advisors are adept at identifying the right moments—like liquidity or birthdays or significant life milestones—to reassess strategies. Legal and insurance advisors ensure that these strategies are sound from an asset protection or risk management perspective. Family psychologists or governance consultants may facilitate conversations around succession planning, interpersonal relationships, and decision-making structures. Nothing is more crucial.
Today, more than ever, families face complex challenges beyond financial management. We all require a team that can holistically serve our needs for expertise in health, wealth, and relationships.
Embracing the Complexity
Let’s assume that Family Offices will play an increasingly important role in managing wealth and the complex needs of families. The sheer scale of assets expected to be transferred between generations in the next decade—estimated to be over $80 trillion USD – makes succession planning and Next Generation leadership development essential priorities for Family Offices. That’s why our team partners with Family Offices. People need our 360 assessment process to confirm who has leadership capacity and what behaviors to develop. People need our Peer Groups to improve communication, reduce conflict, and reduce anxiety about succession.
Let’s also assume that technology will also play a more significant role. Advanced tools, from AI-driven assessments to virtual platforms for family collaboration, are already being used to enhance family governance and communication. Can you imagine a hologram with your 100-year old Elder or Founder in a discussion? Can you imagine 5 generations of family in a meeting, rather than 2-3 generations, as a result of enhanced lifespans? Those technologies will never replace the need for human expertise. Curiosity and humility can never be replaced by AI, and those are two competencies worth developing in most family systems.
Preparing for the Future
To navigate this evolving landscape, Family Office leaders must ensure that their teams can handle both financial and family capital needs. Multidisciplinary teams are not just a trend—they are becoming necessary for Family Offices looking to sustain their success across generations. External advisors provide scaled solutions and reduce costs.
For advisors who serve Family Offices, now is the time to evaluate whether your advisory team is comprehensive enough to address the full range of family needs. Are you prepared to guide your clients through complex psychological and social transitions?
If not, consider expanding your advisory network to include experts who can help you address the evolving challenges facing family offices today. We can help.
Schedule your 1:1 session here.
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