AI Leadership Workshop for HR & Learning Executives

Join fellow HR and Learning & Development leaders for a hands-on, half-day workshop designed to help organizations move beyond AI awareness and experimentation toward building lasting AI capability across the workforce. Generative AI is not another digital transformation initiative. It is changing how knowledge work gets done, how decisions are made, and how employees interact with the processes, policies, and institutional knowledge that define an organization. While many companies have invested in AI awareness sessions, tool training, and experimentation, far fewer have built the operating foundation required to make AI useful, trustworthy, and scalable across the organization. That creates an important opportunity for HR and L&D leaders. As AI becomes embedded in everyday work, HR and L&D have the potential to play a much larger role than simply delivering AI training. They can help build the organizational capability that allows people to use AI effectively, identify where AI can create meaningful value, and ensure AI has the context it needs to perform accurately. During this interactive workshop, The Kendall Project will introduce participants to the Kendall Framework, a structured approach for moving organizations from AI awareness to AI capability. Participants will work through real challenges from their own organizations while exploring: • Why AI workforce programs often plateau after initial training and experimentation • What makes AI transformation different from traditional change management • How HR and L&D can become strategic enablers of enterprise AI performance • How to identify and prioritize high-value AI opportunities across HR and the broader workforce • Why organizational context, including roles, policies, processes, workflows, and institutional knowledge, is critical to AI performance • How to build AI capability inside the organization rather than creating long-term dependency on outside vendors or individual AI experts • What leadership alignment is required to move from experimentation to execution Participants will also apply a problem-first approach to identify potential AI opportunities across areas such as talent acquisition, onboarding, learning design, performance management, workforce planning, and other knowledge-intensive workflows. A major focus of the workshop will be the Context Gap: the gap between what AI knows generically and what it needs to know about your organization to perform effectively. Participants will explore how the knowledge employees use every day can be captured, structured, governed, and made usable by AI. This is not a lecture or a traditional AI training session. Every session is designed to be interactive. Participants will work through exercises, discuss what is actually happening inside their organizations, compare experiences with other HR and L&D leaders, and begin building an actionable path forward. Participants will leave with: • A clearer understanding of what leadership alignment around AI actually requires • A pathway for building evergreen AI skills across the workforce • A practical understanding of the Context Gap and the role HR and L&D can play in closing it • A structured method for identifying and prioritizing AI opportunities • A practical leadership framework for moving from AI awareness to execution • An immediate next-steps plan they can take back to their organization Who should attend: • Chief Human Resources Officers and Chief People Officers • VPs and Directors of Learning & Development • Heads of Talent Development and Organizational Effectiveness • HR transformation leaders responsible for workforce AI readiness • Senior HR business partners advising leadership on AI strategy The workshop is designed for leaders who recognize that the next stage of enterprise AI will require more than giving employees access to new tools. Organizations need to build the skills, context, processes, and ownership required to make AI a durable organizational capability. Date: Wednesday, October 7, 2026 Time: 10:00 AM – 3:00 PM ET Location: Cambridge Innovation Center, 245 Main Street, Cambridge, MA Format: In-person, facilitated workshop Lunch: Included Attendance is intentionally limited to 50 participants to keep the workshop highly interactive and give attendees the opportunity to work through real organizational challenges alongside fellow HR and L&D leaders. Fewer awareness sessions. More AI capability your organization can actually use.