From Curiosity to Core Strategy: Looking Back on Two Years of AI in Business
Release Date: 09/29/2025
AI Knowhow
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What happens when adaptation isn't a phase, but a permanent state of existence? Knownwell CMO Courtney Baker, CEO David DeWolf, and Chief Product and Technology Officer Mohan Rao conclude our change management miniseries by arguing that resilience now beats optimization. The group explores why governance should actually accelerate speed rather than slow it down, and why modern leadership requires the vulnerability to learn in public versus continually exhorting your team to become "AI-first." Plus, Pete Buer shares part two of his interview with innovation expert and author Scott...
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Most leaders have mandated AI pilots, but few can claim it’s fundamentally changed their operations. Why is the gap between experiment and transformation so persistent? Courtney Baker, David DeWolf, and Mohan Rao discuss how to escape the "forever pilot" trap in part three of our change management series. They explore why tools start the change but rituals sustain it, and how to shift AI from a special project to the way business gets done. Pete Buer also joins to break down on why AI-enabled teams outperform lone power users—and the new management skills required to lead them. Then, Pete...
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Is your team actually afraid of artificial intelligence, or are they terrified of being devalued? Courtney Baker, David DeWolf, and Mohan Rao return for Part 2 of our change management miniseries, arguing that resistance isn't obstruction—it's a vital information signal. The panel explores why psychological safety must precede AI literacy and how leaders can acknowledge the "grief" of outdated workflows to build genuine trust. Then, Pete Buer continues his conversation with digital transformation expert Tom Davenport to diagnose "Pilotis"—the industry-wide failure to scale beyond...
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Can you ride a bike with reverse steering? It sounds simple, but it requires unlearning years of muscle memory. That is exactly what AI demands of modern business leaders: the ability to unlearn established rules to keep from crashing. Knownwell CMO Courtney Baker, CEO David DeWolf, and Chief Product and Technology Officer Mohan Rao kick off a new four-part miniseries dedicated to the hardest part of AI adoption: change management. David and Mohan argue that the biggest friction point isn't technology, but the mindset shift from a deterministic world to a probabilistic one where judgment is...
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89% of jobs will be impacted by AI next year. So what does that mean for services firms in 2026? Pete Buer is joined by Chris Barbin and Michelle Swan of Tercera to break down insights from The New Services Playbook—and why “Services as Software” is reshaping everything from pricing models to delivery. They explore why AI isn’t an extinction-level event, how firms are taking share with smaller teams and faster delivery, and what it takes to stay trusted in a world where clients demand outcomes, not hours. Plus: Pete digs into fresh data on workforce shifts and why internal alignment...
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Only 5% of companies are getting real value from AI—so what are they doing differently? Courtney, David, and Mohan unpack the "AI value gap," spotlighting what it actually takes to move from spinning up pilots to driving measurable outcomes, while Pete Buer checks in on Michael Burry’s billion-dollar bet against the AI boom. P ete also sits down with Coframe CEO Josh Payne, who reveals how compounding intelligence and self-improving systems are quietly reshaping customer experiences—and what most companies miss when trying to replicate that success. Learn how to escape the hype, go deep...
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Is it time to redefine the consulting playbook with AI as your new operating partner? From to the shifting role of human consultants, the team looks at how embedded intelligence is reshaping strategy execution and value creation in professional services. This week, Pete Buer breaks down why Cognizant’s enterprise-scale rollout of Claude AI to each of its 350,00 team members AND co-selling it is more than just a tech headline. It's a blueprint for AI as a transformational tool for how services are delivered. Pete and Courtney also dig into what Digg founder and VC investor Kevin...
info_outlineWe’re celebrating 100 episodes of AI Knowhow and asking: what have the last two years of AI actually taught us?
Courtney, David, and Mohan rewind the tape to trace how far AI and executive thinking have come since episode 1 of the show all the way back in September 2023. What began as a curiosity is now a boardroom priority. But while the tech has sprinted ahead, the biggest barriers aren’t technical: they’re cultural, organizational, and deeply human.
The team shares what’s surprised them (Wendy’s drive-thru, anyone?), what still hasn’t landed (where’s the breakout AI-native device?), and what leaders need to carry into the next two years.
And Pete Buer joins to reflect on some of his favorite conversations and the people shaping the future with care, not just code.
It’s a candid, insightful, and sometimes humorous look back, and a launchpad for what’s next.
00:00 Introduction and Milestone Celebration
01:33 Reflecting on Two Years of AI
02:12 Lessons Learned and Future Outlook
06:26 AI in Everyday Life
08:46 Unmet Expectations and Surprises
16:13 Reflections on 100 Episodes
21:09 Looking Ahead to the Next 100 Episodes
Make sure to check out www.knownwell.com.
Watch this episode on YouTube: https://youtu.be/awG-DWpnGEc