Michael Cherry

Michael analyzed and wrote about Microsoft's operating systems, including the Windows client OS, as well as compliance and governance.

Michael was an analyst at Directions on Microsoft from 2000 to 2025. Prior to Directions, Michael worked at Microsoft for more than 10 years where he held a variety of technical and marketing positions, including program manager for Windows Embedded and Windows 2000 IntelliMirror. Michael also worked as a technical evangelist for Microsoft’s Developer Relations Group, advising independent software vendors with enterprise resource planning and accounting products on how to exploit Microsoft’s platforms for their products. Before that, he was a senior architectural engineer for Microsoft, assisting Microsoft’s large corporate customers in understanding Microsoft’s strategy and product directions. Prior to joining Microsoft, Michael designed and supported wide- and local area networks for a variety of companies and industries. Michael received a B.Sc. from Pace University, an M.B.A. from Regis University, and a J.D. and Masters of Laws from the Seattle University School of Law.