This September, I had the opportunity to connect with three incredible Microsoft communities across the Midwest. From leadership development in Minnesota to AI-powered innovation in Chicago, each stop offered a unique perspective on how our customers and community leaders are embracing Microsoft 365, Power Platform, and Copilot. Here's a recap of the journey:
Stop 1: M365 Twin Cities – Brooklyn Park, MN (Sept 19)
The trip began at M365 Twin Cities, a free, community-led event hosted at Hennepin Technical College. This event continues a legacy that began with SharePoint Saturday Twin Cities, running twice a year for over a decade. It’s one of the longest-running Microsoft community events in the U.S., thanks to the dedication of organizers like Wes Preston, Sarah Haase, and Tamara Bredemus, along with a strong network of Microsoft MVPs and volunteers.
Highlights:
- ~400 attendees from across the region, over 700 registered
- 29 sessions across 8 tracks, led by 32 speakers
- Strong community energy, with support from 7 sponsors and giveaways (including LEGO sets!)
- The welcoming speaker dinner—featuring a standout Midwest walleye dish—was a highlight, setting the tone for a day full of energy, learning, and community building
- A warm, welcoming atmosphere fueled by donuts, pizza, and shared purpose
I presented a session titled “Cultivating Trust and Leadership Excellence: Strategies for Respect and Empathy in the Workplace.” The session sparked meaningful conversations about emotional intelligence as a leadership cornerstone.
We explored how respect, empathy, and kindness help build trust within teams, and I shared practical strategies for:
- Deepening domain knowledge
- Empowering autonomy
- Encouraging authentic communication
- Modeling compassionate leadership
Gold Standard for Community Engagement by Donald Donais
It was fantastic to connect with Donald Donais, Director - Cloud Solution Architect in Minneapolis, who has been a true champion of the Twin Cities tech community for well over a decade. As an FTE sponsor and advocate, Don has consistently given his time, energy, and expertise to support local user groups and community events—something every region wishes they had from the Microsoft Field. His dedication has helped make the Twin Cities a vibrant hub for learning and collaboration. Huge thanks to Don for setting the gold standard for community engagement!
Check out this video on what it means to be a community supporter working in the Microsoft field. https://aka.ms/CommunityDaysTwinCitiesDonaldDonais
AND - I couldn’t be more impressed and proud of Harsha Sridharan and Yi Liu for their outstanding session at Community Days M365 Twin Cities!
Their talk, “Engineering People Skills: Building for Humans in the Flow of Work,” was a terrific blend of technical depth with human-centered design. They shared how Microsoft 365 is evolving to help individuals and teams surface, manage, and grow their skills—right where work happens.
From showcasing how skills appear across tools like Outlook, People Companion, Viva, and Copilot, to explaining how AI can infer and highlight strengths without extra effort, they gave us a behind-the-scenes look at building People Skills in M365.
Harsha and Yi didn’t just deliver a session—they sparked confidence and curiosity about the future of skills in the flow of work. Brava! 👏
Stop 2: Chicago Power Platform User Group – Sept 24 (Microsoft Chicago, Aon Center)
At the CMPPUG meetup, I delivered “The Next Phase: Research, Creation & Smarter Decisions in the Age of Copilot.”
- Demonstrated how I used Microsoft Copilot, Researcher, and Create to build the very presentation I was delivering.
- Introduced three AI-centric leadership frameworks:
- 10% Rule for continuous improvement
- 10× Thinking for breakthrough innovation
- 10-10-10 Rule for responsible decision-making
- Engaged in a lively Q&A moderated by Craig Jahnke, lead for the Chicago Innovation Hub, and Microsoft MVP Ralph Rivas.
- and a thank you to Bryan Wofford who went to McCormick to do our tech check for our AI Tour while I was at AON Center.
Highlights:
- 69 attendees in a hybrid format
- Strong interest in Copilot, AI strategy, and responsible adoption
- A huge thank you to Craig and Ralph for their leadership and continued commitment to growing the Microsoft 365 and Power Platform community in Chicago
- Met with David Horstein, the new Director, of the Chicago Innovation Hub in the Aon Center Microsoft Office to talk about Community Days events, user groups and promoting more stories via our MCAG Community News Desk.
Stop 3: Microsoft AI Tour – Chicago (Sept 25)
At Microsoft AI Tour Chicago, Bryan Wofford and I delivered our workshop twice at McCormick Place, both focused on empowering organizations and community leaders to embrace Microsoft AI.
Copilot Ready: Strategy, Data, and Security - Session Code: WRK523-US
Co-delivered with Bryan Wofford, who created the deck and demo and the lab. This hands-on workshop focused on preparing organizations for Copilot deployment. We had close to 200 people total for the sessions. We covered:
- Data readiness and tenant hygiene
- Agent security and governance
- Scaling with built-in Microsoft tools
Participants brought their own laptops and actively engaged in real-time exercises to assess and improve their Copilot readiness.
I also shared a lightning talk - Empowering Community Builders: Join MGCI & CommunityDays
Session Code: LTG171-US
This lightning talk introduced the Microsoft Global Community Initiative (MGCI) and CommunityDays.org, showcasing how these platforms are transforming grassroots tech engagement. We explored:
- How to list and find events
- Opportunities for new and experienced speakers
- Free training and regional leadership connections
Highlights:
- Strong interest and engagement in both sessions
- Keynotes from Judson Althoff, Karen del Vescovo, Bryan Goode, and Jenny Lay-Flurrie
- A packed day of learning, strategy, and connection with customers, partners, and Microsoft engineers
- Was thrilled to see colleague, Anne Krupke, Sr. Product Marketing Manager was on stage to demo with Judson Althoff.
Friday afternoon I went to TedxChicago themed “The Future is Human” to see Nisaini Rexach, Lead, Community Engagement @ Microsoft | Copilot Champ give an amazing session on community building along with 8 other wonderful local speakers. Thank you Craig Jahnke for the intro!
Final Reflections
This trip was a powerful reminder of the strength and momentum within our Microsoft community. From grassroots leadership development in Minnesota to AI transformation in Chicago, I saw firsthand how our tools—and our people—are helping organizations lead with empathy, innovate with confidence, and build for the future.
Our CommunityDays events are always looking for speakers and they are a great way to hone your speaking skills, get feedback directly from customers, partners and our Microsoft MVPs. And connect into The Best Community in Tech. Find events to submit for calls for content and speakers at: Community Days | Homepage #CommunityLuv
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