Summary
After spending nine months helping a large multinational corporation renew their Enterprise Agreement, I did something I should do more often: I sat down and documented everything we learned.
Once I’d finished writing, I realised these lessons shouldn’t just sit in a drawer. I can’t name the corporation for confidentiality reasons. But if you’ve got a Microsoft renewal coming up and tens of thousands of employees across multiple countries, this might be worth your time.
Getting Started Right
What we did in the first few weeks carried through the entire negotiation. We established clear roles, identified who was responsible for what, and agreed on deliverables before the first conversation with Microsoft. That foundation made the actual negotiation far easier.
Once we had the governance framework and key contact points in place, we held a kickoff meeting with all internal stakeholders. We walked through scope, approach, objectives, and what we’d need from each team. The meeting went well. People left knowing what was expected of them, and that positive energy carried through into the negotiation phase.
Early alignment on roles, governance and messaging sets the tone for the entire EA negotiation.
After the kickoff, the core team worked with executive leadership to develop key messages for Microsoft. What did we want them to understand about our position? What were our priorities? Getting alignment on messaging before the first Microsoft conversation meant everyone was telling the same story.
Working with Legal
Legal involvement is essential, but it needs to be focused. The Microsoft Enterprise Agreement is a complex document, and asking lawyers to review the entire thing is a recipe for delays and frustration.
We identified specific areas that needed legal scrutiny: divestiture provisions, sanctions compliance, data protection terms. That precision got us faster and more useful guidance. Lawyers appreciate knowing exactly what you want from them.
The Value of External Expertise
I’m biased here, obviously. But bringing in external consultants was integral to the negotiation process.
Part of it was having pre-existing relationships with pivotal stakeholders. Trust was already established, which made things easier. But beyond that, external consultants bring pattern recognition. We’ve seen dozens of these negotiations. We know where the strategic challenges usually emerge and how to navigate towards successful outcomes.
🖐 For complex EA renewals, structured external guidance can support your internal negotiation team. Learn more: Microsoft Enterprise Agreement Negotiation.
Where We Could Have Done Better
Strategy Flexibility
Our negotiation strategy was thorough. Perhaps too thorough. We’d planned everything in detail, but the plan was rigid. When challenges evolved, we didn’t have contingency scenarios ready.
In hindsight, building in contingency scenarios from the start would have helped. Agile methodologies aren’t just for software development. They work for negotiations too. The depth of planning did give stakeholders confidence, but next time I’d balance that with more “what if” scenarios.
Timing of Key Discussions
We introduced some important Microsoft 365 discussions too late in the process. By that point, changing course on major components required senior management approval, which added complexity and risk.
Timing matters more than you’d think. If something is going to need executive sign-off, surface it early. Don’t wait until the strategy is already in motion.
Internal Collaboration
Stronger internal relationships would have made things easier. When you’re trying to advance strategic aims and build stakeholder consensus simultaneously, having solid connections across the organisation makes a difference. We managed, but better integration of expert insights across teams would have accelerated progress.
Executive Engagement
There was a gap in executive-level involvement. Leadership was supportive but not always actively engaged in key moments. For future negotiations, defining a clearer and more active role for executives before negotiations begin would strengthen the support structure.
What Worked Well
Informal Conversations
Not everything happens in formal meetings. Some of the conversations that propelled negotiations forward were informal ones: corridor discussions, quick calls to clarify positions. These interactions built transparency and allowed both sides to adapt without the formality of scheduled negotiations. They’re worth actively fostering.
Build a Playbook
We created a negotiation playbook that clarified roles and responsibilities, especially for team members who weren’t involved day-to-day. Communication protocols, vendor interaction strategies, explicit escalation processes. Having everything documented meant less confusion and faster decisions when issues arose.
If you don’t have one, build one. It’s one of the most useful things you can do before a major negotiation.
What Held Us Back
Reporting Overhead
The core team spent far too much time on reporting. Updates to internal systems, cross-company communications, status reports for various stakeholders. All necessary in principle, but the volume diverted attention from the negotiation itself, increased stress, and ate into time that should have gone elsewhere.
For future engagements, stripping reporting requirements back to the bare minimum would free up capacity for the work that counts.
Skills Gaps
At director level, there was a noticeable gap in negotiation skills. Not everyone involved had experience with high-stakes vendor negotiations. A training programme tailored to the organisation’s culture and procedures would benefit all negotiation participants. Generic negotiation training wouldn’t cut it; the approach needs to fit how the organisation actually works.
Final Thoughts
Nine months is a long time to spend on a single contract renewal. But the lessons from the experience will pay dividends for years.
Build flexibility into your planning from the start. Surface critical issues early, not halfway through. Work on internal collaboration and get executives actively involved, not just supportive. Strip reporting back to what’s actually needed. And invest in negotiation skills for the people who’ll be in the room. Do all that, and the next renewal should run more smoothly, with better stakeholder engagement and a stronger outcome.