The Future of Leadership: Scaling Teams with Empathy & Purpose | Deb Cupp, President of Microsoft Americas

Finding Mastery with Dr. Michael Gervais

In this fast-evolving business landscape, how do leaders turn setbacks into opportunities for growth?

Today, I’m thrilled to share this conversation with Deb Cupp—the President of Microsoft Americas. Deb embodies the best of leadership – and I don’t say that lightly.

I’ve had an up-close view of how she works – she comes alive at the intersection of staying customer-centric while being able to scale teams within highly complex business landscapes.

Deb is fun, amazing to be around, brings the best out of her teams, and brings the best out of me as well. She’s earned her resilience… it’s no wonder why her teams perform in a world class way.

If you're curious about building a career that's both purpose-driven and high-performing—or how to lead with resilience and empathy—this conversation is packed with actionable insights and wisdom.

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