Win Buy-In for Your AI Upskilling Plan
Tue, Aug 18, 2026
5:00 PM UTC (45 minutes)
Virtual (Zoom)
Free to join
Tue, Aug 18, 2026
5:00 PM UTC (45 minutes)
Virtual (Zoom)
Free to join
What you'll learn
Map three stakeholder perspectives
Use Claude to examine your plan through the business sponsor, manager, and employee perspectives.
Surface hidden assumptions
Identify the evidence, constraints, and unknowns that could change your recommendation.
Keep the judgment human
Turn AI output into validation questions while retaining ownership of the final decision.
Why this topic matters
AI upskilling plans often reflect L&D's view of the problem while missing what sponsors, managers, and employees need. In this live lesson, Andrew Barry will use Claude and a Stakeholder Pressure Test Canvas to expand one proposal across three perspectives, surface hidden assumptions, and identify the human conversations needed before making a recommendation.
You'll learn from
Andrew Barry
Founder, Curious Lion | Former Head of L&D
Andrew Barry is founder and CEO of Curious Lion, where he helps companies build strategic thinking and influence through live cohort programs. Before that, he led Executive Education at KPMG and was Head of Learning at Lobster Ink (acquired by EcoLab). He will demonstrate the AI-assisted perspective-expansion workflow his team uses to keep judgment human.
Previously at
