CEO AI ROUNDTABLE BLOG
AI Isn’t the Answer—It’s the Test:
What CEOs Are Learning From the Frontlines
Strategic insight from Thriveable AI’s private CEO AI Roundtable,
for leaders navigating complexity, not just technology
21 August 2025 | Craig Mansell
Key Insights at a Glance:
- AI isn’t a tech play, it’s a leadership stress test.
- The real challenge? Aligning strategy, culture, and systems.
- Wins come from small, structured bets, not moonshots.
- Our next CEO AI Roundtable is in September. Apply early.
What’s Really Happening Inside Mid-Market Leadership
We recently hosted Thriveable AI’s CEO AI Roundtable, gathering leaders across construction, healthcare, franchising, logistics, and advisory services. Every firm had between 40–260 employees. All are navigating the same challenge: AI feels both inevitable and unclear.
The conversations weren’t about tools. They were about leadership, systems, strategy, and the cultural signals that shape trust.
The message? AI won’t save you. But it will show you where your business is stuck. And if you lead well, it becomes the catalyst for clarity, performance, and transformation.
Five Strategic Signals CEOs Are Sending Now
1. “We know we need to go. We’re just not sure how to move without blowing things up.”
Leaders aren’t resisting AI, they’re resisting missteps. Everyone’s seen scattered pilots, tool fatigue, and transformation initiatives that lost momentum after month three.
Kickstart Strategy Response: Thriveable’s 12–18 month AI Kickstart is designed for this exact scenario. No big bang. Just a structured rhythm to build trust, capability, and momentum.
2. “It felt like therapy.”
That’s what one CEO said about the Roundtable. Because it wasn’t a pitch, it was a reality check. Everyone’s grappling with board pressure, cultural drift, and mounting noise. And everyone felt relieved to know… they weren’t alone.
Kickstart Framing: AI success doesn’t start with tech. It starts with aligned expectations, executive rhythm, and real use case traction.
3. “We got distracted. We found AI tools and then looked for problems.”
Several CEOs confessed to trying the “cool tools” route, only to get distracted by shiny objects and lose strategic alignment.
But when they flipped the approach, results followed:
- Voice agents now convert 90%+ as well as top sales reps—at scale
- AI onboarding flows cut ramp time by 50%
- Weekly “paper cut” automation labs save 100+ admin hours/month
Kickstart Tool: We help teams prioritize the right experiments using our Dot–Dash–Star framework, so you get small wins fast, and scale only what proves its worth.
4. “My job isn’t to control AI, it’s to shape the conditions for others to lead with it.”
This may have been the most powerful idea in the room. These CEOs aren’t trying to master AI, they’re trying to model leadership in motion.
They’re investing in:
- Cross-functional “AI fluency loops”
- Flow engineers and AI working groups
- Cultural signals that reward experimentation, not polish
Leadership Insight: Thriveable AI helps executives redesign their leadership systems, so AI isn’t just introduced, it’s integrated.
5. “It’s not about replacing people, it’s about elevating them.”
Not one CEO saw AI as a tool for job cuts. Instead, they’re using it to free their teams from repetitive drag and refocus them on high-impact work.
Kickstart Philosophy: We begin with augmented intelligence, using AI to elevate human capacity, not erode it. And it’s working.
Why the CEO AI Roundtable Exists
This isn’t a lunch-and-learn. It’s a no-fluff, strategy-first space for CEOs to:
- Benchmark their AI readiness
- Hear how others are unlocking ROI
- Learn the system-level shifts that drive transformation
It’s confidential, curated, and designed for real-time insight, not vendor-led noise.
Join the next C-Suite AI Roundtable – October 2025
Are you a C-Suite leader of a 50-250 person business? Want to lead AI with confidence, not chaos?
Apply now for our next C-Suite AI Roundtable. You’ll leave with strategic clarity, peer insight, and a path forward grounded in real-world traction.
Limited to 10 participants per session for depth and candor.