How Family Businesses Can Win With AI

Reclaim Your Judgment

AI is getting so smooth that it can feel like “help” even when it’s quietly replacing your instincts. After a Vistage [https://www.linkedin.com/company/vistage] workshop with executives and business owners, we walk through a simple idea that keeps showing up in real organizations: reclaim your judgment before you scale anything with AI. We talk about what we’re watching leaders do day to day with ChatGPT and other frontier models, how a few quick prompts can send you down a totally different path, and why that’s dangerous when you’re making high-stakes calls. Your experience, your failures, your wins, and your client context are not “nice to have” extras. They’re the asset. That human wisdom is what keeps AI from turning into generic advice that makes every company sound the same. A standout story brings it to life: a business owner who nearly always wins proposals loads her work into an AI model for “a quick opinion” and almost edits away the very choices that make her proposals effective. We unpack why AI can be super confident with super limited context, and how leaders can set the tone so teams use generative AI responsibly without losing craft, voice, or customer understanding. If you care about AI leadership, executive decision making, and building an AI strategy that actually creates a competitive advantage, this is a practical mindset reset. Subscribe for more, share this with a leader who needs it, and leave a review with your answer: where do you draw the line between AI help and AI control? Enjoying the show? Subscribe, share this with a leader in your organization, and leave a review with the biggest AI question your team is wrestling with. I'm Craig Francisco [https://www.linkedin.com/in/craigfrancisco/], CEO of AI23. [https://www.linkedin.com/company/ai23] I help privately held and family businesses turn their hard-earned domain intelligence into an advantage AI can't hand your competitor down the street. If your team is wrestling with where to start, the best place to begin is a conversation: www.craigfrancisco.com  [http://www.craigfrancisco.com ]

Own The AI Roadmap

AI has a weird way of failing: not with a loud crash, but with quiet drift. You start with a promising idea, then weeks go by as everyone keeps “making it better” without a clear finish line, a real workflow target, or a definition of success. We’re talking about the pattern we’re seeing across companies that actually get results from AI and what the best leaders do differently from day one. We share a hands-on story from a small business with 20 years of history, loads of data, steady inbound demand, and processes that must be documented with care. The breakthrough isn’t a magic prompt or a trendy tool. It’s the owner stepping up like a program manager: guiding development, testing what’s built, and giving consistent feedback so the system matches the messy reality of how work gets done. We also explain why the classic “I want this tool, tell me when it’s ready” approach almost guarantees disappointment with AI implementation. We dig into why custom AI tools are more achievable now, how to think about frontier models versus closed or proprietary models, and how to keep your voice at the center so you’re steering the ship. If you’re serious about AI strategy, AI transformation, and practical business automation, this is a mindset shift worth stealing. Subscribe, share this with a teammate, and leave a review with the workflow you most want AI to improve. Enjoying the show? Subscribe, share this with a leader in your organization, and leave a review with the biggest AI question your team is wrestling with. I'm Craig Francisco [https://www.linkedin.com/in/craigfrancisco/], CEO of AI23. [https://www.linkedin.com/company/ai23] I help privately held and family businesses turn their hard-earned domain intelligence into an advantage AI can't hand your competitor down the street. If your team is wrestling with where to start, the best place to begin is a conversation: www.craigfrancisco.com

How Family Businesses Can Win With AI

Everyone can get AI now, so “we’re using AI” isn’t a strategy anymore. After a talk with HR leaders at the University of Toledo Family Business Center [https://www.linkedin.com/company/university-of-toledo-fbc/posts/?feedView=all], we’re stuck on a bigger question: what actually makes a family business or privately owned company win when the same tools are available to your competitor down the street? We dig into the human reality behind AI adoption inside organizations. The CEO or president feels the urgency to drive strategy. The people doing the work feel the risk, and sometimes real fear, about what changes mean for their jobs. Then HR leaders, CHROs, and talent directors sit right in the middle, trying to translate vision into action while keeping trust intact. That tension isn’t a side note, it’s the work. The heart of the conversation is knowledge versus information. Information is abundant. Knowledge is judgment, especially when the manual runs out and a decision still has to be made. That judgment lives in your domain intelligence: the hard-earned context in your people’s heads, the patterns your teams learned over decades, and the “moat” that helped your business survive tough cycles. We end with a grounded way to approach AI: go back to what made you successful, get clear on what makes you unique, then start small, earn early wins, and let the results compound. Enjoying the show? Subscribe, share this with a leader in your organization, and leave a review with the biggest AI question your team is wrestling with. I'm Craig Francisco [https://www.linkedin.com/in/craigfrancisco/], CEO of AI23. [https://www.linkedin.com/company/ai23] I help privately held and family businesses turn their hard-earned domain intelligence into an advantage AI can't hand your competitor down the street. If your team is wrestling with where to start, the best place to begin is a conversation: www.craigfrancisco.com

Why AI Adoption Will Shift From Tech To People

AI is getting cooler by the week, but I think the next big shift has nothing to do with the newest model or the slickest demo. After spending time at a packed AI event in downtown Cleveland where 500 people chose between four different workshops, I walked away with a clear takeaway about what leaders want today and what they’ll desperately need tomorrow. Right now, most attention goes to the technology. People gravitate toward sessions with “Gen AI” energy because it’s thrilling, tangible, and it feels like a shortcut to transformation. Meanwhile, human centered conversations about how teams actually partner with AI tend to get less love, even when the content is practical and grounded. I get it. The tech is impressive. But the moment companies try to scale beyond experimentation, the real friction shows up fast. My prediction: within the next 12 months, that preference flips. Organizations are going to feel overwhelmed by AI implementation and start “starving for support” on the human side. How do you get teams to understand the tools, trust them, and use them well? How do you structure the organization for adoption, governance, and real value? That is the work that determines whether AI becomes a competitive advantage or an expensive curiosity. If you’re navigating AI strategy, change management, or scaling AI across your business, this short episode is built to challenge your assumptions and sharpen your focus. Subscribe, share it with a leader who’s wrestling with AI adoption, and leave a review with your take: are we heading toward a human first AI era?

Why The AI Boom Forced A Five Month Reset

AI is moving so fast that even seasoned leaders are admitting something they rarely say out loud: this is hard to get your arms around. I’m recording from my car for this quick return, and I want to be candid about why the show went quiet for five months. The acceleration in AI tools, products, and company claims wasn’t just “a lot to track” it was genuinely unsettling, and I needed time to process what it means for real businesses making real bets. What I keep hearing from CEOs and operators is the same double fear: nobody wants to get left behind, but nobody wants to make the wrong move forward. Add the nonstop stream of “new AI workflows” for accounting firms, customer service centers, and every other function, and you get confusion instead of clarity. So we talk about the mindset shift that matters most right now: getting comfortable saying, “I don’t know,” and using that honesty to ask better questions, test smarter, and lead teams through uncertainty. Going forward, I’m committing to practical information over theory. You’ll hear real stories from conversations with companies that are implementing AI, debating AI adoption, and learning where it truly helps and where it doesn’t. Episodes may be short, and they’ll come more frequently only when they bring you clear value. If you want grounded AI leadership insights without the hype, subscribe, share this with a colleague, and leave a quick review. What’s the one AI decision you’re wrestling with right now?