How Our Failed AI Study Led to the Work Our Region Actually Needs
How Turning Disappointment into Creative Energy Revealed What Leaders Actually Need
When we hit "send" on the email canceling our Buncombe County focus shop, the emotions were mixed. Relief that we wouldn't compromise our standards with the sharp weight of a question: What are we doing about it?
After a year of comprehensive research for our "Promises & Risks" AI study, we faced a difficult reality. Despite partnerships with regional institutions, extensive outreach, and clear value propositions, we couldn't generate the participation needed to gather enough meaningful data. Rather than deliver a subpar experience that wouldn't honor people's time, we made the hard call to cancel.
But - What are we doing about it?
It was a question we knew we'd be answering - to our collaborators, to business leaders, and to ourselves. How do we honor the people who invested in this vision with us?
The answer would emerge from an unexpected place—and clarify our understanding of what regional leaders actually need to navigate AI disruption.
[This article is Part 2 of our AI readiness series. Read Part 1: "When Human Readiness for AI Reveals Regional Risk" to understand the comprehensive study that led to these insights.]
When Setbacks Become Breakthroughs
June 5th, 2025 - Sitting together in the very conference room we reserved for our cancelled focus shop, we got down to work. We were booked to deliver a workshop at a popular monthly leadership gathering in the following weeks. That workshop was called: "Crossing the AI Chasm: Courageous Leadership in the AI Era."
We channeled our disappointment into creative energy. For the next two hours, we dove into what was keeping leaders out of AI conversations. We designed frameworks to help us navigate mindsets that block progress. We crafted an interactive experience that would test our theories with real business leaders.
The very questions we were wrestling with—the barriers to engagement, the courage required to navigate uncertainty, the challenge of creating meaningful dialogue around transformation—weren't just research problems. They were the leadership challenges our region's executives face every day.
By the end of the session, we had our workshop. More importantly, we had new, practical tools for instilling the courage required to lead through unprecedented change.
Testing Our Hypothesis: 50 Leaders Engage
Three weeks later, 50 leaders gathered for our "Crossing the AI Chasm" workshop. Assembled was a diverse mix of entrepreneurs, for-profit executives, and technical practitioners.
The energy in the room at times buzzed with enthusiastic conversation during table discussions, and, conversely, fell silent when we presented potential models of AI's impact on white collar jobs.
During our study, we'd identified a crucial insight: crossing the AI chasm may be less about acquiring the greatest technical sophistication. It's about fostering an organizational mindset of learning to work with AI rather than using it as another tool and navigating the humans through change.
This distinction matters more than most leaders realize. AI represents something different than past digital transformations like ERP and remote work. Organizations must develop new ways of thinking, collaborating, and making decisions alongside AI.
Through our interactive workshop, we introduced leaders to three distinct mindsets:
Pioneers tend to move fast and unlock AI's potential, focusing on competitive advantage and business results. They push teams to experiment and advocate for AI investment.
Guardians prioritize protecting what matters most about humanity, emphasizing human oversight and employee impact. They focus on preserving human skills, values, and decision-making authority.
Navigators seek to find the balanced path forward together by bringing all voices to the table. They facilitate discussions between enthusiasts and skeptics while balancing innovation with human-centered concerns.
(Inspired by Michael Rosenberg's "A Human-Friendly Future in the Age of AI")
Participants immediately recognized themselves and their teams in these patterns. More importantly, they left with practical frameworks for inspiring their teams to evolve with AI rather than resist it, concrete strategies for building organizational alignment around AI adoption, and the courage to facilitate productive conversations across perspectives—exactly what today's accelerating pace of change demands from leaders.
Alan in action an AI in Production
At the very end of “Crossing the AI Chasm” workshop, Alan was asked to emcee the AI in Production conference in Asheville just a few weeks later. Here is a short story from his intro at that event.
“...Now, I knew it was about bringing together brilliant AI practitioners, but I asked myself, what do I actually bring to this conversation?
You see, these days, I'm not writing code anymore. I'm no longer a product manager. Nowadays, I advise business leaders on how to navigate their people through transformation and disruption.
And here's what I realized. You all are not gathered because you have AI figured out. You're here because you're smart people trying to navigate something that's moving faster than any of us can keep up with.
I started to reflect on a conversation I recently had with a client. So her name is Sandra, and she runs a service desk for a L&D SaaS company. And she was frustrated because her team wasn't using the enterprise ChatGPT that was recently rolled out.
And I said, "Well, what approach are you taking with your team, Sandra?"
And you guys, I tell you, she responded by sharing the most compelling business case.
She told her team about how this was an awesome learning opportunity to stay current on how to use Generative AI, how to teach it, how they'd get time back to focus on more exciting work, and how ultimately they would be shaping their future instead of having it shaped for them.
I said, "Wow, Sandra, that's excellent. And how are they reacting?"
[Cross arms, frown, look down]
And then Sandra tells me, "Every time they try to use it - disappointment. They say it gives crappy results. It sucks.'"
I said, "Well, Sandra, what's really behind all this arm-crossing?"
"Fear," she said. "They're afraid it's going to take their jobs."
And that was it. Fear. And I explained to her that fear has this way of creating a narrative in our heads - one that blocks us from joining the conversation, and from bringing what we can uniquely contribute to AI adoption.
So Sandra realized the grand promises in her business case weren't speaking to the uncertainty her people felt. So she and I discussed ways for her to more directly address and support them in moving past their fear and into curiosity.
And that's what AI in Production is about - rising above the fear narratives, marketing hype, and scripted product demos to focus on what actually works in the real world. And just like I was able to contribute to Sandra’s AI adoption, each of you have something unique to bring to this conference.”
The Strategic Reality: Why Mid-Market Companies Face the Greatest Risk
The workshop observations supported something else from our research - an emerging pattern that mid-market companies are the most vulnerable. While small companies can pivot quickly and large enterprises have dedicated innovation resources, mid-market companies face a unique squeeze.
These organizations—typically 250-1,000 employees—are large enough that security risks and investment decisions have major implications for their people and communities. They have sufficient complexity that human readiness becomes a challenging change management issue. Yet they often lack the dedicated resources that enterprises use to navigate technological transformation.
This creates a particularly dangerous dynamic: companies that are too big to move fast, too small to absorb risk, and too complex to change swiftly. Without courageous leadership around AI partnership, these organizations risk being left behind by more agile competitors or better-resourced enterprises.
From Experiment to Offering: Meeting the Actual Need
The success of our "Crossing the AI Chasm" workshop confirmed what our cancelled study had actually revealed: regional leaders don't need more information about AI capabilities. They need practical frameworks for developing the courage and strategic clarity required to lead their people through unprecedented change.
Fear travels fast in uncertain times, but what we witnessed that evening was how quickly concrete support and collaborative problem-solving can outpace it. Leaders left energized rather than overwhelmed, equipped with concrete tools rather than abstract concepts.
We indeed pivoted from pursuing comprehensive regional data collection. But what are we doing about it? We developed two programs specifically designed to address the readiness gaps business leaders are facing:
"Crossing the AI Chasm" Workshop provides an accessible entry point for leadership teams ready to explore what AI partnership really means. This four-hour experience focuses on the courageous leadership required to navigate transformation, addressing both strategic and human elements of AI adoption. Participants identify their natural approach to AI decisions, practice facilitating conversations across different mindsets, and develop concrete strategies for building organizational alignment around AI adoption.
Strategic Gen AI Integration offers a comprehensive 90-day pilot program where we work directly with executive teams to build understanding, develop practical experience, and create plans for leading by example through what is genuinely challenging from a human perspective. Through structured coaching and hands-on application, executives typically achieve 50-80% efficiency gains on specific tasks while developing the strategic insight needed for broader organizational implementation.
The Innovation That Matters
Our cancelled study led us to work that mattered more.
By staying committed to our mission while remaining adaptive about our methods, we discovered where Liberated Leaders can best serve regional AI readiness - not through technology capabilities or competitive benchmarking, but by helping leaders develop the courage and strategic clarity required to navigate uncertainty while keeping people at the center of transformation.
The businesses that thrive through AI disruption won't be those with the most sophisticated technology—they'll be those with the most prepared humans.
Leaders who can facilitate conversations across different perspectives. Teams that view change as opportunity rather than threat. Organizations that see AI partnership as enhancement rather than replacement.
Interested in a sample of “Crossing the AI Chasm?” Download our AI Leadership Mindset Assessment and discover where you and your team naturally fall on the leadership spectrum.
Then reach out—let's talk about how we help you move your organization from AI uncertainty to curiosity to competitive advantage.
About the Author
Tina Dao is founder and principal of Liberated Leaders, she partners with business owners and decision-makers to ease the burden of company leadership and embrace the discipline needed to create long-term value. With COO and fractional COO experience, Tina has a wealth of knowledge in technology, operations, strategy, and leadership development. She is a trusted advisor to multiple CEOs, helping them navigate challenges, optimize their businesses, and achieve sustainable growth. Find out more about Tina on our About page.
About the Author
As a Success Architect at Liberated Leaders, Alan leverages 20 years of experience in technology leadership and consulting to help businesses optimize their technology strategies, gain an edge, and scale their operations. He is a twice certified executive and leadership coach who firmly believes that true business transformation can only occur with mindful investment in people and technology. Find out more about Alan on our About page.
Note: This article was 85% human generated and 15% machine (AI) generated.