What do you get when you combine a conversation about AI with a guided wine tasting? Surprisingly, it’s a great way to unpack one of today’s biggest business challenges: how to lead through AI transformation.
Recently, ExecOnline and Udemy hosted a virtual roundtable for senior HR, L&D, and business leaders to talk about exactly that. It wasn’t just a discussion about tools or trends. The event also included a wine tasting led by master sommelier Jennifer Foucher, which ended up being the perfect metaphor for the night’s theme: the best pairings are thoughtful, balanced, and intentional. The same goes for AI and leadership.Here are seen strategies to help you foster a workplace where your best employees choose to stay, grow alongside you, and contribute to the company’s success.
The Real Challenge with AI: It’s People, Not Just Tech
ExecOnline CEO and Co-Founder Stephen Bailey opened the session with a point that resonated with our attendees: AI is moving fast, and the pressure to adapt is real. But the hardest part isn’t technical. It’s human. Leaders must ensure their teams have more than just access to tools. They need the right mindset and the confidence to use them.
Udemy’s Chief Marketing Officer, Genefa Murphy, added important context. According to McKinsey & Company, AI could contribute up to $4.4 trillion in global value. That’s massive. But here’s the gap: according to Udemy’s GenAI Transformation: Perspectives on Leadership Survey Report, 86% of employees say they know they need AI training, yet only 14% have actually received it. The issue isn’t a lack of interest. It’s a lack of meaningful support.
And a blanket approach won’t cut it. What truly helps is learning that’s directly connected to the work people do every day. It needs to be role-specific, relevant, and practical.
From Awareness to Adoption: Understanding the Three Waves of AI Transformation
Genefa also laid out a helpful framework for how companies typically move through AI adoption. There are three main stages:
● Wave 1: Automation – Using AI to handle repetitive, routine tasks and boost efficiency.
● Wave 2: Augmentation – AI starts to support decision-making and enhance more complex workflows across teams.
● Wave 3: Agentic AI – AI begins to act more independently and begins to reshape how work actually gets done.
Most companies today are still in transition between Waves 1 and 2, seeing value mainly through time savings and productivity gains. However, the real transformation begins in that third wave. Getting there isn’t just about upgrading your tech stack. It requires a shift in how teams work, how leaders lead, and how companies build capability.
Why AI Transformation Starts with Humans
Throughout the conversation, leadership coach Jason Regier focused the conversation on one key idea: AI is a technical topic, but transformation is a human process.
Leaders in the group shared what they’re seeing on the ground. Several recurring themes emerged:
● Employees are afraid AI will replace them.
● There’s confusion around how AI is actually supposed to be used.
● Some leaders don’t feel confident experimenting with it.
● People are using AI but not talking about it openly.
● There’s resistance to change, especially when it involves vulnerability.
The most forward-thinking companies are tackling those issues head-on. Some are building internal “AI sandboxes” where teams can safely test and learn. Others are encouraging leaders to talk transparently about how they’re using AI themselves. That kind of openness helps normalize AI across the organization.
And then there’s the skills conversation. Everyone agreed we need to stop referring to the human element as “soft skills” and start recognizing them as “power skills”. Skills like critical thinking, emotional intelligence, adaptability, creativity, ethical decision-making, and relationship-building. These are the things AI can’t replicate, and they’re the skills that will matter more than ever in an AI-enabled workplace.
As one participant put it, “AI isn’t going to take your job. But someone who knows how to use AI better might.”
A Leadership Framework Built for the AI Era
To help organizations think through how to lead this shift, ExecOnline’s Chief Operating Officer, Matt Castaldo, introduced their Leadership Development Framework. It focuses on four dimensions where leaders need to grow:
● Strategic Leadership – Delivering innovation and long-term value
● Operational Leadership – Driving efficiency and execution
● People Leadership – Inspiring and supporting teams
● Self Leadership – Staying grounded, resilient, and adaptablePeople Leadership – Inspiring and supporting teams
To navigate the AI era effectively, leaders must apply their skills and capabilities fluidly across these dimensions. This allows them to align teams behind a strategy, plan proactively, and facilitate cross-functional collaboration to drive transformation at speed.
Wine Meets Wisdom
It might have seemed like a fun add-on at first, but Jennifer Foucher’s guided tasting turned out to be a pretty brilliant metaphor. As she walked everyone through a Sauvignon Blanc and shared unique pairing tips, it became clear that the same principles apply to leadership. It’s all about context, balance, and being open to trying something new. You don’t have to be perfect. You just have to be intentional.
Many attendees shared that the biggest blockers aren’t tech limitations. They’re cultural.
What Comes Next
AI is already changing how work gets done. The question isn’t whether your company will use it. It’s how ready your leaders are to guide that change. The easy part is adopting new tools. The harder part is helping people think and work in new ways.
That’s where ExecOnline and Udemy come in. Both platforms are built to deliver real-time, role-based learning that equips leaders with the skills they actually need. It’s expert-driven, data-informed, and aligned with the challenges today’s businesses face.
AI is here. The future is happening now. And the way forward starts with people who know how to lead through it.
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Executive Summary at a Glance
Here’s a visual snapshot of the key themes and leadership insights shared during the ExecOnline and Udemy roundtable:
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Further Reading and Resources
● Types of AI: Understanding Artificial Intelligence – Udemy
● The GenAI Transformation: Perspectives on Leadership – Udemy Survey Report
● The Cybernetic Teammate – Harvard Digital Data Design Institute
● Superagency in the Workplace – McKinsey & Company
● ExecOnline Website
● Udemy Business Website