Deb Cupp, President and Chief Revenue Officer for Microsoft’s Enterprise Business, joins the ManpowerGroup’s Work Intelligence Lab Podcast to discuss why AI adoption varies among employees and clients—and what organizations can do to close the gap. 

Deb explains that education, understanding, and ongoing skilling are key to reducing fear and uncertainty around AI, helping people recognize the opportunities it creates. She argues that successful AI transformation is not just about the technology itself, but about effective change management, with people at the center and practitioners closest to business challenges helping shape the solutions. 

She also highlights the importance of combining strong leadership direction with bottom-up momentum, guided by clear ROI and KPIs to ensure organizations focus on meaningful outcomes rather than chasing “shiny objects.” 

Drawing on real-world examples, Deb shares how Microsoft sales teams use Copilot to prepare for customer conversations and proposals—driving a 9% improvement in outcomes. In healthcare, AI-powered transcription and paperwork automation are reducing administrative fatigue and improving the experience for clinicians by 30–40%. 

Chapters: 

00:00 AI Adoption & Fear of the Unknown 

02:48 Unexpected Learnings & Change Management 

05:17 From Productivity to Outcomes 

07:21 Building Trust in AI Adoption