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

Michael Gervais (0:00)

In this fast-evolving business landscape, how do leaders turn setbacks into opportunities for growth? Welcome back or welcome to the Finding Mastery podcast, where we dive into the minds of the world's greatest thinkers and doers. I'm your host, Dr. Michael Gervais, by trade and training, a high-performance psychologist. And today, I'm really excited to welcome Deb Cupp, who embodies the best of leadership. I do not say that lightly. Deb is the president of Microsoft Americas. It's a huge job now. And 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. You're going to hear that. She's amazing to be around. She brings the best out of her teams. She brings the best out of me. She's earned her resilience. It is no wonder why her teams perform in a world class way. If you are 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. A quick note, if you find value in these conversations, I would love for you to take a moment to leave us a rating and a review on Apple Podcasts, Spotify or wherever you're listening. Your feedback helps us reach more people to grow this incredible community. So let's jump right into this week's episode with the inspiring Deb Cupp.

Deb, this is so much fun to sit with you.

Deb Cupp (1:43)

I'm so excited to be here. I've been excited about this for weeks.

Michael Gervais (1:48)

Have you?

Deb Cupp (1:48)

Yes.

Michael Gervais (1:49)

That's really good.

Deb Cupp (1:49)

I love spending time with you.

Michael Gervais (1:50)

Ditto.

You have so much to offer, obviously, inside of the big job you have at Microsoft. But the way that you contour your life and the vibrance that you have when you walk into a room, that's something I want to open up to better understand. What is that psychology that's sitting right underneath that? So we'll do that as we go. Let's just start at the top. How are you right now?

Deb Cupp (2:15)

I'm great. I'm great.

Michael Gervais (2:18)

Yeah.

Deb Cupp (2:18)

It means I'm getting energy from what I'm doing. It means that I'm surrounded by people I enjoy. I'm actually just coming off of a couple of days with customers, and that gives me such joy and energy. I'm fascinated by what they do and how they do it. So I feel like when I'm learning, when I'm spending time with people I love, when I'm getting energy from the work that I'm doing, I feel great.

Michael Gervais (2:40)

Energy from the work I do feels like something that I think most people would say, Oh, I want that.

Deb Cupp (2:46)

Yeah.

Michael Gervais (2:46)

Is it about the fit or is it about your psychology, whatever you are going to do, that you would carry that model with you?

Deb Cupp (2:55)

I think fit is important so that you're in a place doing a thing that you believe you can give to.

Michael Gervais (3:03)

Okay.

Deb Cupp (3:03)

So for me, it has to be something where I feel like I'm contributing and that I'm learning. So I think fit is important, but I also think it's what you bring. So it's weird. I'm one of those people that says like, how have I been so lucky that I've had so many jobs that I love? And it can't just be the job, right? So there's something about sort of how I think about it.

Michael Gervais (3:23)

Yeah, I feel like you would, anywhere you go, you would naturally bring something to that environment that allows you to feel the way that you do and kind of shape your thoughts and your words in a way that brings the energy that I know you.

Deb Cupp (3:39)

Yes.

Michael Gervais (3:39)

Yeah, so there's like an interaction, but you're saying that there's something I'm doing that I feel like I want to contribute in a certain way.

Deb Cupp (3:46)

Yes.

Michael Gervais (3:46)

And the environment, I'm always looking for environments that are kind of bouncing that back.

Deb Cupp (3:50)

Yes. So and I can tell when there's an environment that's not necessarily bouncing that back in the way that I want. And when that happens, I find the need to move to a different environment. So if I feel like the environment isn't giving me the space to be me, then I'm not interested in being in that environment.