For over 30 years, we are
Independent. Experienced. Proven.
In a world of automated noise, judgment is the ultimate premium.
For 30 years, Fortune 1000 leaders have called on Directions on Microsoft for the decisions that define their tenure. When the cost of being wrong is measured in nine figures, “vendor-neutral” isn’t enough. You need independent conviction.
We provide the strategic intelligence required when vendor guidance is misleading and automated insights are dangerously shallow. We don’t have sales targets. We don’t have partner pressures. We have judgment.
High-Stakes Decisions Require Eyes-Wide-Open Strategy
Microsoft moves fast, often leaving its customers to find the “landmines” in the roadmap. We ensure your ROI isn’t eroded by technologies that aren’t ready for the enterprise or products Microsoft is already quietly abandoning.
We serve as the human red team for CIOs and Procurement leaders when:
- Technology Targeting: Distinguishing between Microsoft’s marketing “vision” and actual, deployable product maturity.
- Audit Defensibility: Identifying structural licensing risks before they become unplanned capital expenditures.
- Contractual Leverage: Engineering terms that protect your budget for years, not just the next quarter.
- Strategic Vetting: Pressure-testing your “big bets” against the reality of Microsoft’s internal shifts and policy changes.
The Human Difference: Context Over Code
LLMs and chatbots can summarize a licensing guide, but they cannot navigate a negotiation. They can’t tell you “why” a policy changed or “how” that change will be used against you at the renewal table.
Our experts average 25+ years of senior leadership. We are former Fortune 500 CIOs, Microsoft product engineers, and veterans of the Microsoft Business Desk—the highest authority on deal structure. We don’t approximate expertise; we live it.
Ground Truth as a Competitive Asset
At the Fortune 1000 level, “information” is a commodity. Insight is the advantage.
- Practitioner-Led Analysis: Stripping away the vendor narrative to find the financial reality.
- Early Signal Intelligence: Identifying pricing and roadmap shifts months before they hit your desk.
- Defensible Strategy: Providing the evidence-based logic required for Board-level approval.
When the Answer Has to Be Right
Organizations don’t come to us to confirm a consensus. They come to us to find the flaws in it before the contract is signed.
When the stakes are high, trust isn’t found in an algorithm. It’s found in the independence and experience of people who have seen every cycle of the system.
Directions on Microsoft. Real-world expertise and judgment no chatbot can simulate.
Founders
Former Microsoft Executives
Microsoft Insider Experience in Technology
Microsoft Insider Experience in Licensing, Negotiation and Account Management
Respected Independent Voices
