The Microsoft 365 Community Conference is always one of the most valuable events of the year for Microsoft IT professionals. It brings together the people responsible for keeping Microsoft 365, Copilot, Exchange, Teams, SharePoint, and even Entra ID running securely and efficiently, as well as the vendors, experts, and practitioners who help them navigate constant change.
This year in Orlando, the ENow team had the opportunity to connect with customers, partners, and the broader Microsoft community through three standout moments: conversations at our booth, another unforgettable scheduledMaintenance party, and a packed conference session led by our CEO, Jay Gundotra.
One of the best parts of the M365 Conference is the opportunity to have real conversations with the administrators and IT leaders who manage Microsoft environments every day.
This year, our booth brought a little extra energy to the expo hall with an F1 racing theme. Attendees could step into our racing simulator and test their skills on the track for a chance to win 2 top prizes. It was a fun way to bring some friendly competition to the conference floor. Our top two spots battled it out for the top spot with only 375 MILLISECONDS between them.
We also handed out Formula 1 (F1)- race-car-shaped stress relievers and a collection of industry-themed stickers that quickly became popular takeaways throughout the event.
Beyond the racing action, the booth was a hub for meaningful discussions with Microsoft 365 administrators, identity teams, and security leaders facing a familiar set of challenges:
These conversations reinforced a common reality: organizations are under increasing pressure to move quickly with AI initiatives, but many are still working through foundational governance and operational readiness.
That gap between executive urgency and operational readiness became a central theme throughout the week.
ENow CEO, Jay Gundotra, took the stage alongside Microsoft MVPs Daniel Glenn and Sander Berkouwer, with special guest Sean Hurley, for a timely and practical session on Governance and Copilot readiness.
Their message was clear: Copilot does not create governance problems; it exposes the ones that already exist.
Microsoft Copilot only surfaces content that users already have permission to access. That means longstanding issues like oversharing, stale permissions, weak content/site ownership, and unmanaged enterprise applications become far more visible once AI enters the picture.
The session focused on two critical areas in need of governance:
As Jay framed it, Copilot is where information governance debt and application governance debt become visible at the same time.
One audience poll during the session asked attendees to rate their governance maturity on a scale of one to five. Not a single attendee rated their organization at five. Most identified themselves at a two, a result that closely aligns with Gartner's Digital Employee Experience maturity findings.
That honesty reflects what many organizations are experiencing today. The challenge is not whether to adopt AI, but how to do so responsibly and at scale.
The session offered a pragmatic roadmap for organizations preparing for broader Copilot deployment:
The takeaway was simple: you do not need perfect governance before deploying Copilot. But you do need enough visibility and control to scale it with confidence.
Or, as the session concluded: if you fix only one thing, fix ownership. It often improves Microsoft 365 governance, application governance, and Copilot readiness simultaneously.
Of course, the M365 Conference is not just about sessions and expo halls.
We hosted our scheduledMaintenance party, also known as the hottest tech party at select Microsoft IT conferences. This was surely the event to attend! With over 200 attendees, this party brought together Microsoft professionals, MVPs, customers, partners, and friends for an evening of great conversations, networking, dancing, and a chance to unwind after a full day of technical content.
It originally launched in 2014, at the Lync Conference. It now has its own reputation and brand, which is followed by major MVPs, and IT Pros in the Microsoft community.
scheduledMaintenance has become a Community Conference tradition, and for good reason. It captures what makes the Microsoft community unique: a willingness to share knowledge, exchange ideas, and build relationships that extend far beyond any single event.
Some of the best conversations happen outside the conference rooms, often over a drink or bite, when practitioners can compare notes on everything from Entra app governance to Exchange troubleshooting to the realities of Copilot rollout.
This year's conference underscored several important trends for Microsoft organizations:
For ENow, these themes closely align with the challenges we help organizations address every day, from Microsoft 365 governance and license optimization to Entra application governance and operational visibility.
To everyone who stopped by our booth, attended our session, or joined us at scheduledMaintenance, THANK YOU!
The Microsoft community continues to be one of the most engaged, knowledgeable, and collaborative communities in technology. We are grateful to be part of it.
We are already looking forward to continuing these conversations and to seeing everyone again for the next one.