Friday, January 30, 2026
FRIDAY – AI FOR THE C SUITE
Read time: 7-8 min · Read online
Hi, it’s Chad. Every Friday, I serve as your AI guide to help you navigate a rapidly evolving landscape, discern signals from noise and transform cutting-edge insights into practical leadership wisdom. Here’s what you need to know:
1. Sound Waves: Podcast Highlights
This past Monday I was joined by Amanda Greenwood, founder of Real Teams Coaching and former senior consultant who delivered a $500 million, 5-year government transformation program. We discuss the hidden reason your AI training isn’t translating to results: the gap between teaching tools and managing the human threat response that stops adoption cold, and what Great Ormond Street Hospital leaders learned about making change actually stick. My next solo episode also drops this coming Monday, 2.02.2026. Check either out wherever you get your pod fix.
Apple · Spotify · iHeart · Amazon · YouTube
Subscribe for free today on your listening platform of choice to ensure you never miss a beat. New episodes release every two weeks.
2. Algorithmic Musings: The 10% Trap
A CEO recently told me that their AI strategy was “working great.” When I asked what success looked like, he said they’d cut proposal drafting time in half. I nodded. Then I asked what his competitors were doing with AI. He paused. “I don’t actually know.”
That conversation kept rattling around in my head when new research from VirtuousAI and Chief Executive Group landed. They surveyed 300+ mid-market CEOs about AI adoption, and one number jumped off the page: 78% said their primary AI objective is efficiency and cost reduction. Only 19% are looking at AI as a transformational opportunity.
I’ll be blunt. If you’re in that 78%, you might be building the organizational equivalent of a really fast horse. Meanwhile, the automobile is rolling off the assembly line.
Here’s what I’m calling the 10% trap. You use AI to make your current way of doing business 10% faster or cheaper. That’s real progress. It shows up in quarterly reviews. Nobody argues with it.
But what happens when your competitor doesn’t stop at faster proposals? What happens when they wire that automation into their pricing model, their margin targets, their capacity forecasting? When the system doesn’t just write proposals faster but decides which business is actually worth winning?
Suddenly you’re not competing on speed. You’re competing against a company that has reimagined how decisions get made.
And it’s not just your current competitors you should be watching.
Here in middle market land, I’m witnessing something new: the rapidly evolving ability of individual humans to build their ideas into existence. In previous eras, this required resources. Other humans, access to capital, specialized equipment.
What I’ve seen repeatedly over the past two years are “non-techie” individuals using AI tools to not only solve problems but build the future. A client of mine with zero technical background learned to use AI tools over two months and built a custom business intelligence platform for their sales team. It knits together six different data sources from six different platforms and surfaces cross-selling opportunities that were previously invisible. No IT department. No six-figure software contract. Just persistent curiosity and the willingness to learn.
This should terrify every leader in the 78%. Barriers to entry have dropped. What you’ve built is no longer gated, moated, or otherwise protected in the manner you believe it to be.
The research surfaced another telling pattern. More than half of CEOs want AI to improve data analysis and decision-making. Translation: most leaders are comfortable letting AI inform their decisions. They’re not comfortable letting AI make them. The researchers call this the gap between “AI-as-analyst” and “AI-as-operator.” It’s a trust issue, and it’s understandable. It’s also where ROI goes to die.
The right question isn’t “How can AI help us?” That framing keeps AI in the advisory box. The better question: What is AI accountable for? Which outcomes should AI be responsible for improving?
That’s a fundamentally different conversation. Most leadership teams haven’t had it yet.
I recently sat down with Chris Happ, CEO of VirtuousAI, to dig into this research and what it means for mid-market leaders trying to figure out their next move. That conversation drops on the podcast in April.
In the meantime, here’s my challenge: Look at your current AI initiatives. Are they making your existing model 10% better? Or are they building toward something that changes what your organization is capable of?
If the honest answer is the former, you’re not behind yet. But you’re standing still while the ground moves beneath you.
3. Research Roundup: What the Data Tells Us
VirtuousAI and Chief Executive Group
State of AI Adoption in the Mid-Market: How CEOs Are Approaching and Using AI, Fall 2025
Read the full report
New survey data from 300+ mid-market CEOs just confirmed my anecdotal suspicion: everyone believes in AI, while almost nobody’s actually executing.
The numbers that matter: 98.5% of mid-market CEOs say AI offers value for their business. But only 7% have a company-wide strategy with multiple initiatives running. Over half (52%) are stuck in pilot purgatory. The gap isn’t belief. It’s execution.
What this means for your Monday morning: Your competitors are just as lost as you are. That’s actually good news. The 7% with coordinated strategies are building compounding advantages while everyone else accumulates disconnected experiments. Starting now with an integrated approach beats adding another isolated pilot.
The catch: Three barriers are reinforcing each other. 86% cite lack of AI expertise, 81% struggle with system integration, and 65% have data quality problems. You can’t solve this by buying more tools. You need to unify your data foundation first, then automate.
Action item: Before your next AI investment, audit what you already have. Which tools connect to each other? Which create technical debt? The companies pulling ahead aren’t the ones with the most experiments. They’re the ones who stopped experimenting at the edges and started connecting AI to specific business outcomes.
4. Radar Hits: What’s Worth Your Attention
Is Your Algorithmic Pricing a Lawsuit Waiting to Happen? The RealPages settlement cost apartment landlords $141 million after their AI pricing tool was deemed a “hub-and-spoke conspiracy.” If your pricing engine uses competitors’ confidential data, you could face the same exposure. Before signing with any AI pricing vendor, ask: Can you explain how the algorithm works? Are we required to follow its recommendations? Keep a paper trail.
AI Arbitrators Are Coming for Your Contract Disputes. The American Arbitration Association just launched an AI-powered arbitrator for construction cases, with insurance disputes next. The system still requires human sign-off, but resolution times will compress significantly. If you’re budgeting for dispute costs this year, factor in faster (and potentially cheaper) arbitration paths for routine contract claims.
5. Your Next Move
Not sure if you’re stuck in the 10% trap? Let’s find out. I have a few slots opening up in Q2 for mid-market CEOs who want a clear-eyed assessment of where their AI initiatives actually stand and what it would take to move from efficiency plays to competitive advantage. No pitch deck, no generic framework. Just a focused conversation about your specific situation. Reply to this email if you want to talk.
Until next week,
Stay safe. Stay healthy. Be strong. Lead well.
Chad
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