10 December 2026 | 15:30 GMT 10:30 EST
Your Microsoft renewal may be months away, but decisions about what you ultimately pay are being made now.
Microsoft agreements are increasingly complex, spanning Microsoft 365, Azure, Copilot and AI, changing commercial models and evolving business requirements. The biggest risk isn’t simply paying too much. It’s entering your next negotiation without the data, time or commercial leverage to challenge what’s on the table.
In this practical webinar, Gareth Redshaw will reveal five warning signs that your next Microsoft renewal could be at risk, and explain what you can do about them before your negotiating options narrow
Where Microsoft Negotiations Are Won and Lost
What you’ll learn:
- The 5 signals that your Microsoft renewal is at risk, from poor demand visibility to leaving preparation too late.
- Where organizations lose negotiating leverage, and why building your position around entitlements, consumption, and business needs needs to start early.
- The Azure commitment traps to watch for, balancing discounts and commitments against changing cloud consumption.
- How Copilot and AI are changing Microsoft negotiations, and why modeling demand matters before committing at scale.
- How independent market intelligence strengthens your position, helps you benchmark offers, and challenges assumptions.
- What good looks like in practice, through a real-world enterprise Microsoft negotiation.
Why attend?
For many enterprises, a Microsoft renewal is one of the largest commercial events in the IT calendar. But negotiating leverage isn’t created when Microsoft’s proposal arrives. It’s built earlier, by understanding what you own, what you’re actually using, what the business will need next and where you have room to negotiate.
If your EA, MCA or major Azure commitment is approaching, this webinar will help you identify where your organization may be exposed and what you can do while you still have options.
Designed for CIOs and IT leaders, Procurement and Strategic Sourcing, SAM and ITAM, FinOps and Cloud teams, Microsoft licensing and vendor management teams, and Finance leaders responsible for technology spend.
Presenter Presenter
Gareth Redshaw
Executive Director – Optimization & Company Strategy
Gareth leads Livingstone’s Business Strategy and Optimization Practice, bringing more than 20 years’ experience in IT commercial negotiations with some of the world’s most recognizable organizations. He specializes in complex major vendor agreements across Microsoft, Oracle, IBM, and SAP, and has delivered average savings of 38% across major renewals.
A strong advocate for moving beyond traditional SAM compliance towards measurable commercial impact, Gareth combines commercial negotiation expertise with a deep understanding of technology strategy and licensing. As an independent advisor, he helps organizations challenge vendor positions, negotiate from strength, and achieve better commercial outcomes.