Strategy
Assessment

Validate direction and avoid costly mistakes

Face Decision Uncertainty with Confidence

Navigating Microsoft’s complicated array of technologies and licensing options can be overwhelming. With countless versions and overlapping capabilities, targeting the wrong technologies or versions – or licensing incorrectly – can result in cost overruns and compounded problems.

Our Microsoft Strategy Assessment reduces this risk by validating your long-term Microsoft technology decisions through a customized, expert-led workshop. Designed to align your technology choices with your business needs, this service ensures you invest in solutions that truly add value—not just those Microsoft wants you to buy.
During the workshop, our Microsoft technology and licensing experts:

  1. Work with your team to understand your future technology needs.
  2. Analyze your existing deployments and planned purchases.
  3. Validate your choices or recommend better alternatives based on our deep, up-to-date knowledge of Microsoft’s ecosystem and strategy.

We provide a comprehensive report documenting the rationale for each technology selection and licensing recommendation. This ensures you’re fully prepared for your next Enterprise Agreement (EA) renewal and in control of the negotiation process.

Covering the Full Microsoft Spectrum

  • Desktop
  • Collaboration
  • Management
  • Databases
  • Security
  • Regulatory compliance
  • Infrastructure
  • Development and test
  • And others as required

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.

Microsoft Technology Strategists

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

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