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Get in-depth access to unbiased analyses, roadmaps, product reports, decision kits, reference guides and more to make informed Microsoft enterprise decisions.

A sample of the over 14,000 items in our growing library of expert content

Updated: April 14, 2025   Analyst Report
What Is Advanced Data Residency? by Wes Miller
Updated: April 27, 2025   Analyst Report
Copilot Agents: How to Avoid Surprising Licensing Costs by Rob Sanfilippo
Updated: May 13, 2025   Blog
Microsoft to provide security updates for M365 apps on Windows 10 for three more years  by Mary Jo Foley Available To All
Updated: May 1, 2025   Podcast
Microsoft: A Look Back from Inside  by Mary Jo Foley Available To All

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Licensing Training

This intensive, 18+ hour “boot camp” is the most complete and up-to-date training on Microsoft licensing available. You get the knowledge and understanding to intelligently evaluate your Microsoft licensing options and keep your organization compliant without overbuying. You also learn a disciplined process and proven negotiation strategies for optimizing your next Enterprise Agreement (EA).

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Full-Cycle Advisory & Negotiation Support

Advisory Services
Contract & EA Negotiation

Get expert guidance in every stage of your Contract and Enterprise Agreement negotiations, from initial preparation to securing the best terms. Our experts leverage proven tactics to ensure you get favorable pricing, flexibility, and alignment with your organization’s goals.

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Stay prepared and compliant with our audit defense and license verification services. We’ll help you identify and address any compliance gaps, minimizing risk and positioning your organization for a successful audit outcome.

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Strategy Services
Our Top Microsoft

Experts & Analysts

Fortune 500 CIOs, former Microsoft executives and product engineers, negotiators, and leading industry journalists – our team has the deepest expertise and experience in the industry.

Jeff Parker Jeff Parker

Jeff Parker oversees Directions on Microsoft’s publishing and training businesses. He also advises clients on… more

Dean Bedwell Dean Bedwell

Dean Bedwell works with organizations to optimize their Microsoft licensing agreements. He also trains organizations… more

Rob Horwitz Rob Horwitz

Rob Horwitz analyzes and writes about Microsoft licensing programs and product licensing rules. He also… more

Mary Jo Foley Mary Jo Foley

Mary Jo Foley is the Editor in Chief at Directions on Microsoft. Before joining Directions,… more

Andrew Snodgrass Andrew Snodgrass

Andrew analyzes and writes about Microsoft’s data management, business intelligence, and machine learning solutions, as… more

Jim Gaynor Jim Gaynor

Jim leads the Directions on Microsoft editorial team and has been writing about technology since… more

Greg DeMichillie

Greg brings with him over two decades of engineering, product and GTM experience. He has… more

Wes Miller Wes Miller

Wes Miller analyzes and writes about Microsoft’s security, identity management, and systems management technologies. Before… more

Barry Briggs Barry Briggs

Before joining Directions on Microsoft in 2020, Barry worked at Microsoft for 12 years in… more

Michael Cherry Michael Cherry

Michael analyzed and wrote about Microsoft’s operating systems, including the Windows client OS, as well… more

Rob Helm Rob Helm

As managing vice president, Rob Helm covers Microsoft collaboration and content management. His 25-plus years… more

Rob Sanfilippo Rob Sanfilippo

Before joining Directions on Microsoft, Rob worked at Microsoft for 14 years where he designed… more

David Berry

David specializes in SharePoint and Microsoft 365. He spent 25 years as a solution architect… more