Rich Kaplan and I had an incredible conversation about what it really means to bring truth to power. From his years as a Microsoft executive to his current role as a mentor and advocate, Rich has always been someone who leads with honesty, clarity, and heart—and that’s exactly why he’s one of my favorite humans.

We talked about the importance of speaking up, the expectations that come with leadership, and the very real challenges that exist inside corporate culture. Rich shared how AI is reshaping not just the workplace but also how we live and learn. We discussed adaptability, continuous growth, and the need to stay curious—especially as we face things like ageism and rapid technological change.

We also explored the intersection of AI and healthcare, the role of mentorship in shaping careers, and how feedback and self-awareness are non-negotiables for effective leadership.

Rich and I are similar in that we both say it like it is. You’ll hear him repeat one of his core beliefs throughout our conversation: “Bring truth to power.” It’s who he is, and it’s why I’ve been intentional about managing our relationship and making sure we connect every month. Every time we talk, I walk away with something new—whether it’s wisdom, perspective, or one of his hilarious behind-the-scenes stories from Microsoft back in the day.

As a bonus, Rich even shared memories of working with nearly every major Microsoft leader—from their quirks and strengths to the moments that defined the company’s culture.

This conversation is full of leadership lessons, personal growth, and reminders of what it looks like to lead with courage and candor.

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