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
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...
Video
Updated: January 9, 2026 · by Barry Briggs
Looking Ahead to 2026: Microsoft’s (and Your) Challenges
With AI, Microsoft is making the biggest bet in its history — a move many are comparing to the Industrial...
Blog
Updated: December 2, 2025 · by Barry Briggs
CIO Talk: Microsoft Gets IQ
Let the semantic-layer wars begin! Barry Briggs provides an overview of the 3 "IQs" Microsoft introduced at Ignite, why they're...
Blog
Updated: October 15, 2025 · by Barry Briggs
CIO Talk: The Enterprise Semantic Layer: The Missing Link for AI (and Microsoft)?
Enterprise data models, semantic layers, ontologies...where is Microsoft in this area -- possibly key to the success of AI in...
Blog
October 2, 2025 · by Barry Briggs
CIO Talk: Compliance in the World of AI: Are You Ready?
Does AI change absolutely everything in compliance?
Webinar
September 24, 2025 · by Barry Briggs
Microsoft Compliance Update 2025
In the new AI-centric world, it’s easy to overlook how this new technology can open organizations up to regulatory and...
Video
Updated: September 10, 2025 · by Multiple Authors
Directions Podcast. Season 4. Episode 15. Enterprise Copilot Adoption: Lessons from the Field.
PwC Principal James Farhat joins Directions analyst Barry Briggs and Mary Jo Foley to discuss early real-world wins and challenges...
Blog
August 15, 2025 · by Barry Briggs
CIO Talk: What Open-Source Models Mean to Enterprises
What do open-source language models mean to enterprise applications and IT? Directions analyst and former Microsoft IT CTO has some...
Blog
July 30, 2025 · by Barry Briggs
CIO Talk: AI in Five Years – Which Way Will It Go?
Where will enterprise computing and AI be in five years? Directions analyst Barry Briggs envisions a couple of very different...
Blog
Updated: July 18, 2025 · by Barry Briggs
CIO Talk: Vibe Coding and What It Means To You
Do AI assistants really accelerate development? Can they replace your developers? Directions' analyst Barry Briggs has thoughts.