UnsuckM365

05/13/2026

Most SharePoint scars do not start with terrible decisions. They start with reasonable shortcuts that survive too long, pick up dependencies, dodge ownership, and eventually become someone else’s problem. After presenting SharePoint at 25: Lessons from the Scars at M365 Philly, I created a post about the pattern I keep seeing across tenants: ambition, shortcut, debt, exposure, and clarity.

SharePoint scars follow a pattern: ambition, shortcut, debt, exposure, and clarity. AI just made the pattern harder to ignore.

05/08/2026

I just delivered “SharePoint at 25: Lessons from the Scars” at M365 Philly and I think today was a bit of a turning point for me as a speaker. This was the first session I’ve done with no screenshots, tech demos, or “click here, then click there” walkthroughs. Instead, I focused on storytelling, lessons learned, audience interaction, governance scars, AI implications, and the decisions we make in Microsoft 365 that quietly age over time. The room was engaged, the conversations were great, and my unhinged puns landed exactly the way I hoped they would.

Something Karuana Gatimu said at The Microsoft 365 Community Conference has been stuck in my head: “we need to teach critical thinking.” I’ve been feeling that for a while, and that’s the approach I went with today. Features change, admin centers move, buttons get renamed, and demos eventually expire, but helping people understand patterns, consequences, tradeoffs, and better ways to think about the platform lasts a lot longer. I think I finally found my footing with the kind of sessions I want to keep building: less feature tour, more field report from the trenches.

Huge thanks to everyone who attended, participated, laughed at the painfully relatable parts, and shared a few scars of their own.


Copilot Governance AI CommunityRocks
WorkInProgress MVPBuzz

05/05/2026

I made SharePoint talk like Yoda for May the 4th because apparently I cannot be trusted with new AI features. Then I took it one step further and created a SharePoint skill that gives every day of the year its own personality. One skill, 365 voices, and a completely unnecessary amount of chaos. Business critical? Absolutely not. A fun way to understand how SharePoint skills work? Absolutely.

A fun look at SharePoint skills, using a daily voice calendar that changes how AI responds in SharePoint every day of the year.

05/03/2026

If you missed it live, I hosted and moderated a session at the Microsoft 365 Community Conference 2025 with fellow MVPs Vlad Catrinescu, Laura Rogers, Richard Harbridge, Pete Simpkins, and Sean Bugler to talk about where SharePoint is headed and what skills still matter.

A practical recap of my Microsoft 365 Community Conference 2025 livestream with MVPs Vlad Catrinescu, Laura Rogers, Richard Harbridge, Pete Simpkins, and Sean Bugler on the future of SharePoint, AI…

05/03/2026

I joined fellow MVP Laura Rogers on Power Hour at the Microsoft 365 Community Conference 2025 to talk SharePoint modern UI updates, Copilot, agents, metadata, governance, and what it takes to get AI-ready in Microsoft 365. Because, shocking no one, AI still does not magically fix bad collaboration habits.

A practical recap of my Power Hour conversation with SharePoint MVP Laura Rogers at the Microsoft 365 Community Conference 2025, covering SharePoint modern UI updates, Copilot, agents, metadata, go…

04/29/2026

The Microsoft 365 Community Conference was packed with learning, , , , , and community, but the biggest reminder was simple: none of us are figuring this out alone. The tech is moving fast, but the people are still the best part. Grateful for the conversations, hugs, chaos, and support that keep us grounded while everything changes.



https://unsuckm365.com/2026/04/29/the-m365-community-conference-2026-reminded-me-once-again-we-cannot-figure-this-out-alone/

04/29/2026

The Microsoft 365 Community Conference was packed with learning, , , , , and community, but the biggest reminder was simple: none of us are figuring this out alone. The tech is moving fast, but the people are still the best part. Grateful for the conversations, hugs, chaos, and support that keep us grounded while everything changes.

A personal recap of The Microsoft 365 Community Conference 2026 in Orlando, reflecting on SharePoint, Copilot, AI readiness, governance, community, mentorship, and why Microsoft 365 is moving too f…

04/15/2026

A few weeks after my first MVP Summit, I had enough distance to process it.

What stayed with me most was not clarity, but the opposite. Honestly, that was reassuring. Being at Microsoft HQ reminded me that even the people building this stuff are still learning in real time.

There is something special about learning alongside people you once learned from afar.

An honest recap of my first MVP Summit, with reflections on AI, Microsoft HQ, mentorship, burnout, and what it means to belong in the Microsoft 365 community.

03/03/2026

This past Friday, I recorded a special edition of Behind the Tenant with Richard Harbridge at Microsoft Community Day Knoxville about 25 years of SharePoint. From folder debates and workflow experiments to Power Platform and Copilot exposing your content strategy; we cover what kept it alive, what we do not miss, and why AI will not fix bad governance.

In this special edition of Behind the Tenant, recorded at Microsoft Community Day Knoxville, we reflect on 25 years of SharePoint, including governance, folders versus metadata, workflows, Power Pl…

03/02/2026

SharePoint didn’t survive 25 years by chasing hype. It survived by becoming infrastructure, powering Teams, OneDrive, Copilot, compliance, and the entire Microsoft 365 ecosystem. Substance outlasts spectacle. Day 25 of my 25 days of SharePoint series closes the arc with defiance, nostalgia, and a call to celebrate what endured.

After 25 years, SharePoint remains the backbone of Microsoft 365 because it chose integration, governance, and endurance over hype. Substance outlasts spectacle.