Microsoft Expert Desk

Decision support whenever you need it

Making the wrong decision about Microsoft technologies or licensing can be costly. With an overwhelming number of options and policies, it’s natural to have questions. Unfortunately, searching online often leads to frustration, and relying on Microsoft or its resellers may not align with your best interests.

Your Trusted Source for Microsoft Answers

Our Expert Desk service gives you direct, phone-based access to an entire team of Directions on Microsoft analysts, including:

  • Former Microsoft product engineers.
  • Former Fortune 500 CIOs (and even a former Microsoft CTO).
  • Former Microsoft Business Desk executives—the highest level of Microsoft licensing expertise.

Extend Your Team with Unmatched Expertise
Each Directions expert specializes in a specific area of Microsoft technology or licensing, acting as an extension of your team. They provide the impartial, authoritative advice you need to make confident, strategic decisions – insights you’d love to have in-house but can’t always find or afford.

Trustworthy, Unbiased Guidance
Use the Expert Desk to get clear, impartial answers to your most urgent Microsoft questions. Whether it’s understanding licensing options, comparing products, or planning deployments, you can count on Directions to provide insights tailored to your needs—not influenced by Microsoft’s sales objectives.

Recent Expert Desk Topics

Our team tackles tough questions and challenges every day, including these and more:

  • Cross-tenant domain sharing
  • Microsoft endpoint security services
  • Microsoft 365 for Government
  • Usage rights for fonts in Word
  • Licensing SQL Server for developers
  • Azure Hybrid Benefit
  • Microsoft Unified Support
  • Microsoft 365 E3 versus E5

Built to Deliver Unprecedented Value

35 to 2,000,000 Users Support for organizations of any size
Microsoft-Focused Singularly committed to helping you successfully navigate the Microsoft landscape
Serving Clients
Since 1992 Decades of experience to support your decision-making
50x Average Expected ROI Knowledge we've proven can give you the negotiating edge

The Best Team Anywhere

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

Licensing & Negotiation Experts

Dean Bedwell
Dean Bedwell

Licensing Expert & Negotiator

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

Larry Fletcher
Larry Fletcher

Negotiation & Audit

Larry is a former Senior Licensing Executive at Microsoft with over 15 years experience negotiating complex deals within both the…more

Steven Kelley
Steven Kelley

Negotiation & Audit

Steve Kelley works with organizations to optimize their Microsoft licensing agreements and protect them from future licensing liabilities. Before joining Directions…more

Kevin Glunt
Kevin Glunt

Negotiation & Audit

Before joining Directions on Microsoft, Kevin spent eleven years at Microsoft in financial management, including five years as the senior…more

Scott Campos
Scott Campos

Negotiation & Audit

Prior to joining Directions on Microsoft, Scott was a Microsoft licensing consultant at IDC and Software Licensing Advisors. Before that,…more

Joshua Osborne
Joshua Osborne

Negotiation & Audit

Joshua Osborne helps organizations to optimize their Microsoft licensing negotiation outcomes. He also works with companies to self-audit their Microsoft…more

Technology Experts & Strategists

Barry Briggs
Barry Briggs

Analyst

Before joining Directions on Microsoft in 2020, Barry worked at Microsoft for 12 years in a variety of roles, including…more

Greg DeMichillie
Greg DeMichillie

Analyst

Greg brings with him over two decades of engineering, product and GTM experience. He has held leadership positions at premier…more

Mary Jo Foley
Mary Jo Foley

Analyst

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

Andrew Snodgrass
Andrew Snodgrass

Analyst

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

Rob Sanfilippo
Rob Sanfilippo

Analyst

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

Wes Miller
Wes Miller

Analyst

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

Jim Gaynor
Jim Gaynor

Analyst

Jim leads the Directions on Microsoft editorial team and has been writing about technology since the early 1990s. Most recently…more

David Berry
David Berry

Analyst

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

Rob Horwitz
Rob Horwitz

Analyst

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

Rob Helm
Rob Helm

Analyst

As managing vice president, Rob Helm covers Microsoft collaboration and content management. His 25-plus years of experience analyzing Microsoft’s technology…more

Michael Cherry
Michael Cherry

Analyst

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