Finding Mastery with Dr. Michael Gervais

What Microsoft’s Culture Shift Can Teach You in 2026 | Kathleen Hogan

31 snips

Dec 10, 2025

In this engaging conversation, Kathleen Hogan, Chief Strategy and Transformation Officer at Microsoft, discusses her transformative role in reshaping Microsoft's culture. She emphasizes the importance of empathy, curiosity, and purpose in leadership, drawing on her personal experiences, including overcoming cancer. Kathleen shares insights on fostering psychological safety in teams and the positive role of AI in enhancing human potential. Ultimately, she highlights that effective leadership is rooted in care, not just knowledge.

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ANECDOTE

Healing Confirmation From Her Son

Kathleen Hogan recounted shaving her head during chemo and asking her four-year-old son if he liked her with or without hair.
Her son replied, "mommy, I love you just the way you are," which healed her and clarified her core worth.

ANECDOTE

Choosing Presence Over Perfection

Kathleen described planning a trip to Ireland with her 81-year-old grandfather who then had a stroke and said, "I'm never going to see Ireland."
She chose to go home, prioritizing presence over perfect grades and avoided long-term regret.

INSIGHT

From Know-It-All To Learn-It-All

Microsoft shifted its culture from "know-it-all" to "learn-it-all" to value how work gets done as much as the outcome.
Grounding the company in growth mindset freed people from performative certainty and encouraged curiosity.

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What if the future of work isn’t about technology at all — but about unlocking more humanity in each other?

On today’s episode, we sit down with Kathleen Hogan, Chief Strategy and Transformation Officer at Microsoft, and one of the key architects behind the company’s cultural reinvention. Kathleen helped lead Microsoft’s shift from a “know-it-all” to a “learn-it-all” culture — embedding empathy, curiosity, and growth mindset across a global workforce of more than 220,000 people.

In this conversation, Kathleen and Dr. Michael Gervais explore what it really means to lead with humanity. She shares the moments that shaped her leadership — from facing cancer twice, to redefining success through purpose and connection — and the inner work required to help others unlock their potential.

In this conversation, we explore:

How Kathleen helped Microsoft reimagine its culture from the inside out
Why purpose and empathy are the foundation of effective leadership
How to build psychological safety and courage in high-performing teams
What it means to lead with curiosity instead of certainty
The role AI can play in empowering — not replacing — human potential

At its heart, this episode is a reminder that leadership isn’t about knowing more — it’s about caring more.

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