Not Too Big, Not Too Small – TechCon is Just Right

In our latest Polaris episode, I sat down with David Wilhelm, President of TechCon 365. Their next conference is coming up later tnis month in Seattle, June 23-27, with Karuana Gatimu landing the keynote, and over 150 sessions from Micosoft and the community.

We covered a lot of ground – from AI adoption challenges to the magic of community-building at tech conferences.

The AI Skills Gap

AI is advancing rapidly, but many organizations are stuck at the starting line. According to a recent IBM global survey, limited AI skills and expertise is the top barrier preventing enterprise AI deployment (33% of large companies report this).

 This is where training and upskilling come in – and why events like TechCon 365 are so important. In fact, David started TechCon (SharePointFest at the time)back in the late 2000s precisely to meet this need. People were “craving targeted training in bite-sized chunks” that they could immediately take back to the office.

That practical focus remains at the heart of TechCon 365. It’s not just about flashy keynotes (though those are fun); it’s about equipping attendees with skills they can apply right away. As David put it: “Smaller scale events let us deliver richer, deeper, practical content that attendees can use immediately.”

The Mid-Sized Conference Advantage

Mid-sized events offer distinct benefits. TechCon 365 is a great example – it’s not a tiny 100-person meetup, but it’s also not a Death Star-sized mega-conference like Ignite. It sits in that sweet spot of a few hundred to a thousand attendees.

Why does that matter? For one, you’re not just a number in the crowd. David highlighted that at a ~800-person event, “attendees feel seen and heard” in ways that are hard to replicate at a 20,000-person show. You have far more access to experts – whether it’s chatting with Microsoft engineers, MVPs, or industry thought leaders. When you have a question, you can actually get face time with the speaker after a session, rather than elbowing through a sea of people.

Perhaps most importantly, events like TechCon 365 can focus on practical, day-to-day content. During my decade at Microsoft, I helped put on plenty of big marketing moments, and they’re fun. But I also know the common feedback: “This is cool… but when can we actually get it?” At TechCon, the emphasis is balanced: you get forward-looking insights and deeper dive sessions that deliver immediate value.

Diversity, Accessibility, and Team Learning

Another theme we discussed is the diversity of attendees you find at TechCon 365. It’s not just about background or demographics (though TechCon does draw a diverse crowd in that regard too); it’s about diversity of roles and budgets. You’ll see developers, IT pros, business analysts, and decision-makers all learning together under one roof. That cross-pollination is valuable – a SharePoint admin can wander into a Power Platform session or an Azure data workshop and come away with new ideas.

Importantly, TechCon’s regional, medium-scale approach makes it more accessible for teams. Not every company can afford to send six people on cross-country flights to a conference. But if an event is within a few hours’ drive (or a short domestic flight), suddenly it’s feasible to bring the whole team. David shared how many organizations send cohorts of 5-6 folks. They’ll gather each morning at breakfast, compare notes on what they learned, and coordinate which sessions to cover that day. It turns a conference into a team learning retreat. Your SharePoint guru hits one track while your BI expert hits another, then you regroup and swap insights. The result: everyone gets more value, and the organization gains a 360° view of what’s happening.

TechCon’s model – rotating through cities like Seattle, Atlanta, Dallas (and beyond) – means more folks can join in. That local/regional reach even extends internationally; last year’s Seattle conference drew attendees from all 50 U.S. states and 14 countries! It’s proof that if you build an event that’s accessible and valuable, people will come (sometimes from the other side of the globe).

Community Building

One of my favorite parts of this episode was when David connected community building to an unexpected source: cooking. He mentioned watching Chef’s Table (a Netflix documentary series profiling world-renowned chefs) and noticing how restaurants can become community hubs.

But the point David made is a great one: Conferences, like restaurants, should create a space “where everybody knows your name.” (If you remember Cheers, that theme song line will resonate.) At TechCon 365, the aim is to foster that Cheers-like welcome. They’re creating a Microsoft Community Lounge where anyone can chat with product team members or MVPs in a relaxed setting. There are even “Ask the Experts” sessions and AMA panels where no question is too basic or too advanced – the goal is to make sure everyone feels included and leaves with their questions answered.

Looking Ahead to TechCon 365 Seattle and Beyond

David gave us a preview of TechCon 365 Seattle – coming up on June 23rd. It’s their flagship conference, and this year it’s bigger than ever: three co-located events under one roof (TechCon 365 for Microsoft 365 topics, PWRCON for Power Platform, and DATACON for Azure Data/SQL).

Synozur is a Platinum Sponsor and will be delivering more than a dozen sessions.

You can save 15% on registration with code SYNOZUR.

Seattle in summer also means great food (as a fellow foodie, David made sure to mention hitting his favorite Pacific Northwest restaurants) and unrivaled access to Microsoft’s backyard. If you’re looking for deep-dive content across Microsoft 365, Power Platform, and Fabric/Azure data, Seattle is the place to be this June.

Beyond that, mark your calendars: TechCon 365 Atlanta is coming in August, and TechCon 365 Dallas in November.  You can also get in touch with David on LinkedIn.

Polaris is available on Apple, Spotify, Amazon, YouTube or wherever you get your favorite podcasts. Thanks.

Show Notes

Sound Bites

• “At a 600-person event, you’re not just a number – attendees feel seen and heard.” — David Wilhelm

• “As Microsoft’s world grows, our community grows with it. We just give them more to explore at each event.” — David Wilhelm

• “Not everyone can fly to Vegas or SF for a mega-conference. Regional events open the door for folks who’d be left out otherwise.” — David Wilhelm

• “A conference isn’t just sessions. Like a great local restaurant, it can become a place where everybody knows your name.” — David Wilhelm

  
  

References

News and Data Points

Gartner (July 27, 2023) – Press release reporting that 52% of organizations say risk factors are a critical consideration when evaluating new AI projects. https://www.gartner.com/en/newsroom/press-releases/2023-07-27-gartner-survey-finds-55-of-organizations-that-have-deployed-ai-take-an-ai-first-strategy-with-new-use-cases

IBM (Jan 10, 2024) – IBM Global AI Adoption Index 2023 research found limited AI skills and expertise is the top barrier to AI adoption (~33% of enterprises cite this). https://newsroom.ibm.com/2024-01-10-Data-Suggests-Growth-in-Enterprise-Adoption-of-AI-is-Due-to-Widespread-Deployment-by-Early-Adopters

SS&C Blue Prism (Mar 28, 2025) – Global survey of business leaders: 35% cite lack of AI skills/expertise as a major barrier to adopting AI (tied for #1 barrier). https://www.blueprism.com/resources/blog/ai-agentic-agents-survey-statistics/

Microsoft Global Community Initiative (MGCI) – Microsoft’s program to support community-led events worldwide (e.g., Community Days). https://adoption.microsoft.com/en-us/microsoft-global-community-initiative/

Social: David Wilhelm | LinkedIn

Pop Culture

Chef’s Table (Netflix series) – Documentary series showcasing world-class chefs; referenced as an analogy for community building. https://en.wikipedia.org/wiki/Chef%27s_Table

Cheers (TV sitcom) – 1980s sitcom set in a bar “where everybody knows your name”; referenced to describe a welcoming community vibe. https://en.wikipedia.org/wiki/Cheers

The Bear (FX/Hulu series) – TV series about a Chicago restaurant, popularized the phrase “Yes, chef.” Referenced humorously in the episode. https://en.wikipedia.org/wiki/The_Bear_(TV_series)

Events

Mastering Your AI Rollout: Success Strategies | June 12, 2025 (TribalHub Online)

Business Strategy Master Class | June 17, 2025 (Teams Online)

TechCon 365 Seattle | June 23-27, 2025  (Seattle Convention Center)

FY26 Forward - Microsoft Partner Success Strategies - July 29 (Teams Webinar)

TechCon 365 Atlanta | August 11-15 (Georgia World Congress Cente)r.

TechCon 365 Dallas - | November 3-7, 2025 (Irving Convention Center)

Microsoft Ignite 2025 – Nov 17-21, 2025 (San Francisco, CA). 

ESPC25 | December 1-4, 2025 (Convention Centre Dublin (CCD) Ireland)

Fabric Community Conference (FabCon) – Microsoft Fabric Community Conference (upcoming event focusing on Microsoft Fabric and data/A.I.). https://fabricconf.com

Production

Polaris is produced with the help of our friends at Riverside.fm. Our theme song, “Alternative Dream” is provided courtesy of Adobe.  Additional music and sound provided by IndieGuy Records. Graphic design by Josh Brantley.

Chapters

00:00 Introduction to David Wilhelm and Tech Conferences

04:12 The Evolution of Tech Conferences

07:32 Transitioning from SharePoint to Microsoft 365

11:51 The Benefits of Mid-Sized Events

15:25 Diversity and Accessibility in Tech Events

18:29 Engagement Opportunities for First-Time Attendees

21:37 Upcoming Events and Future Plans

24:43 Community Building Through Food and Events

26:44 Staying Connected with David Wilhelm

27:40 Conclusion