Before joining Directions on Microsoft in 2020, Barry worked at Microsoft for 12 years in a variety of roles, including as Chief Technology Officer for Microsoft’s own IT organization for 5 years. Prior to Microsoft, Barry spent several years as CTO for several successful startups, and before that, 11 years at Lotus Development, where he was the lead developer for Lotus 1-2-3, the best-selling application of its time, and a Lotus Fellow.
Barry holds a B.A. and an M.A. from the University of Massachusetts at Amherst.
Latest Content by Barry Briggs
Video
Updated: September 28, 2026 · by Barry Briggs
AI Doom or Golden Age? Three Smart Guys: Season 1. Episode 6
Are we doomed, or on the cusp of an AI-powered golden age? Can Claude's Constitution, Microsoft's Humanist AI Code of...
Blog
September 24, 2026 · by Barry Briggs
Thoughts on Microsoft’s Humanist AI Code of Conduct
Microsoft's Humanist AI Code of Conduct is yet another in a series of efforts to establish guardrails on AI. Will...
Video
Updated: September 10, 2026 · by Multiple Authors
How and Why We Built an AI Assistant. Season 5. Episode 14.
Directions on Microsoft built its own AI Assistant to help with Microsoft technology and licensing queries. Analysts Barry Briggs and...
Video
Updated: June 11, 2026 · by Barry Briggs
Too Big To Flail. Three Smart Guys: Season 1. Episode 5
Unlock the Future of AI: How Microsoft, Google, and Apple Are Shaping the Next Intelligent Client Are you ready to...
Video
Updated: April 16, 2026 · by Barry Briggs
Can AI Save Collaboration Software? Three Smart Guys: Season 1. Episode 4
After decades of incremental change, collaboration software is at an inflection point, and AI could have a big influence on...
Blog
Updated: April 6, 2026 · by Barry Briggs
Is Microsoft Lost in the Frontier?
In which Barry makes the somewhat radical proposal that we are in an extraordinary new period of innovation -- and...
Video
Updated: March 23, 2026 · by Barry Briggs
Three Smart Guys: Is Office dead? Season 1. Episode 3.
In this episode, Barry Briggs, George Gilbert, and Peter O’Kelly unpack how Office, Copilot, and AI are reshaping everyday work...
Video
Updated: March 3, 2026 · by Barry Briggs
Three Smart Guys: It’s All About the Data. Season 1. Episode 2.
Directions' Barry Briggs and industry analysts George Gilbert and Peter O'Kelly discuss how AI’s dependence on data is reshaping Microsoft’s...
Video
Updated: January 30, 2026 · by Barry Briggs
Three Smart Guys: Microsoft’s 2026 Challenges. Season 1. Episode 1.
In this inaugural episode of the TSG podcast, Directions' Barry Briggs, along with industry analysts George Gilbert and Peter O'Kelly,...
Blog
January 29, 2026 · by Barry Briggs
Will Microsoft’s AI Strategy Pay Off?
AI products and services are front and center, yet again, for Microsoft in 2026. What could go right -- and...