554: Microsoft’s Dean Carignan on Using AI to Boost Joy, Focus, and Productivity at Work

The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving

What if the key to innovation isn’t a process, but a mindset that travels across boundaries, disciplines, and decades?

From international development to McKinsey to leading AI strategy at Microsoft, Dean Carignan has built his career at the intersection of systems, people, and impact. Now, as co-author of The Insider’s Guide to Innovation at Microsoft, he’s helping organizations rethink how real innovation happens, not just in startups or labs, but in legacy institutions and global companies.

In this episode, Dean shares lessons from two decades at Microsoft, where he’s worked across Xbox, Office, cognitive services, and AI research. He also reflects on why innovation is ultimately about people, not products, and how leaders can create space for meaningful change, even inside complex organizations.

We explore:

• How Dean moved from solving global problems at the World Bank to driving change inside one of the world’s largest tech companies

• The power of being a “boundary crosser” and why innovation happens in the in-between

• Why mission often outperforms money as a motivator, especially in hiring for impact

• The overlooked value of storytelling in innovation (and how case studies bring ideas to life)

• How AI is transforming not only productivity, but the very nature of scientific discovery

• Why learning to build with agents may be the most valuable skill of the next decade

Dean also shares practical examples of how he uses AI today, from research to writing to daily decision-making, and why “thinking about thinking” is the leadership advantage most people overlook.

Whether you're guiding a team through change, building a new product, or trying to stay ahead of the AI curve, this conversation offers a grounded, human-centered approach to innovation in a time of exponential possibility.

Dean Carignan’s career spans international economic development, startup ventures, and strategic roles in technology. He is an alumnus of Georgetown University and INSEAD, he was a charter member of McKinsey & Company's advanced technology practice.

During his 20 years at Microsoft, he has guided new businesses, including the early internet division, Xbox, and multiple Al efforts through the critical growth phases to their first billion dollars in revenue.

Most recently, Dean has focused on leading AI innovations within Microsoft Research and the Office of the Chief Scientist. His intrapreneurial spirit, deep institutional knowledge, and expansive internal network made the behind-the-scenes perspective of The Insider's Guide to Innovation at Microsoft

Get Dean’s book here: https://www.innovationatmicrosoft.com/

The Insider's Guide to Innovation at Microsoft

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