From Spectators to Participants: The Surprising Speed of Association AI Adoption

Looking back at the Sidecar Sync podcast journey from Episode 1 (October 2023) to Episode 100 (September 2025), what has surprised the Sidecar team most?

Not that associations would adopt AI. Sidecar and the greater Blue Cypress family of companies have been talking about AI in the association space for years. The inevitability of AI transformation was never in question.

The shock would be the speed. The scale. The shift from consumers to creators.

When we launched the podcast in October 2023, associations were still figuring out whether to allow ChatGPT in the workplace. By Episode 100, association professionals are building their own AI solutions, deploying AI agents, and creating new member products. In less than two years, the entire relationship between associations and technology transformed—not gradually, not cautiously, but with a velocity that surprised even those of us who've dedicated our careers to driving this change.

In Episode 100, our Chairman and podcast host Amith Nagarajan reflected on how the percentage of associations actually implementing AI far exceeded what anyone would have predicted two years ago. That's not something you hear often from someone who's been evangelizing AI for a decade.

Let's look back at how we got here.

The Evidence Was Building From the Start

Even before we launched the podcast, the signals were there. Spring 2023 should have been our first clue—Sidecar ran a webinar with "Generative AI" in the title and 1,700 people showed up. For context, that was an order of magnitude larger than a typical webinar for us at that time. The follow-up AI bootcamps were immediately oversubscribed. We couldn't create seats fast enough.

The hunger was real. Associations weren't just curious—they were desperate to understand what this meant for them.

By digitalNow 2023 in Denver, the rooms were packed with association professionals trying to wrap their heads around AI. The sessions focused on understanding what AI was and what it could mean for associations. People were taking notes, asking questions, staying after sessions to talk more.

Then something shifted.

By digitalNow 2024 in DC, just one year later, the entire energy had changed. Associations weren't asking what AI could do—they were showing what they'd built. The Wednesday showcase featured actual implementations. Breakout sessions were led by association executives demonstrating production systems they'd created.

In our AI Mastermind group, the evolution was even more dramatic. Early sessions were about possibilities and concerns. Now participants were presenting their own projects—not concepts, not pilots, but working systems serving real members.

>> Related: If you want to see what associations are actually building right now, join us at digitalNow 2025, November 2-5 in Chicago, where you can move from watching to doing!

What Changed Everything

Several forces converged to create this shift in adoption.

ChatGPT made AI tangible practically overnight. Before November 2022, AI was algorithms and theory. After ChatGPT, it became a tool you could use before breakfast. Associations didn't need to understand neural networks—they just needed to type questions and get answers.

The economics flipped completely as AI implementation went from requiring millions in capital investment to costing less than your monthly coffee budget. Enterprise AI became subscription AI, and the financial barrier essentially disappeared.

Meanwhile, member expectations shifted faster than strategic planning cycles could accommodate. Members who spent their evenings chatting with ChatGPT showed up expecting their associations to offer similar experiences, and board conversations evolved from "Should we explore AI?" to "Why don't we have this yet?"

Perhaps most importantly, the pandemic had already shattered the myth that associations couldn't change quickly. Organizations that pivoted to virtual events in weeks had proven their adaptability, so when AI arrived, the muscle memory for rapid transformation was still fresh.

The Reality on the Ground

Let's talk about what associations are actually building right now. Not planning. Not piloting. Building and deploying.

Member knowledge bases with AI assistants. Associations are loading decades of content, research, and expertise into AI systems that can answer member questions instantly, accurately, and conversationally. 

Intelligent member matching for networking. AI systems that analyze member profiles, interests, and goals to facilitate meaningful connections. 

New AI-powered revenue products. Associations are creating AI tools as member benefits—personalized learning paths, AI research assistants, automated compliance checkers. 

Automated personalization at scale. Email campaigns that adapt to individual member interests. Conference agendas that customize based on attendee goals. Content recommendations that actually match what members need.

Early 2024, being "AI curious" marked you as innovative. Now, in late 2025, not having AI implementation is becoming conspicuous. What people ask has shifted from "Are you exploring AI?" to "What are you doing with AI?"

The Acceleration Nobody Predicted

Traditional technology adoption in associations follows predictable patterns: awareness, investigation, committee formation, vendor evaluation, budget allocation, pilot program, gradual rollout—maybe a 2-3 year timeline at minimum.

Current AI adoption looks different. Someone attends a webinar, tries ChatGPT that afternoon, builds a prototype within a week, gets budget approval within a month, and launches to members within six months.

Associations are building custom solutions instead of waiting for vendors to create them. When a tool costs $20 per month and can be built in an afternoon, the risk calculation changes. The cost of trying is now less than the cost of a single committee meeting to discuss whether to try.

The sector is proving that given the right tools and compelling reasons, associations can move as fast as any industry. The careful, deliberate culture hasn't disappeared—it's operating at a different clock speed when circumstances demand it.

Coming soon in Ascend 3rd Edition, we'll be sharing real case studies from associations leading this transformation. Actual stories of implementation, complete with challenges faced and lessons learned.

The Next 100 Episodes

We predict that by Episode 200 of the Sidecar Sync podcast, associations will have deployed thousands of AI agents. Real-time AI avatars will become standard for member service, offering video calls with AI representatives who know your entire content library, can answer complex questions, and provide personalized guidance 24/7 to every member.

World models will enable associations to run complex simulations, answering questions like "What if we changed our certification requirements?" or "How would this affect member retention?" AI will simulate thousands of scenarios before you make a single real change.

The compound advantage of early adoption becomes more pronounced every day. Associations that started experimenting in 2023 now have two years of AI experience—they've made mistakes, learned lessons, and refined approaches. That experience can't be purchased or rushed. Every month matters now, and the association that waits until 2026 to begin won't just be three years behind—they'll be generations behind in AI capability.

The Choice Point

AI will transform your association's operations and member services—that's settled. What matters now is whether you're watching others build the future or building alongside them.

Some associations are still in the audience, taking notes, forming committees, and discussing possibilities. Others have moved from their seats to the stage, tools in hand, creating the next generation of member value.

The surprise of the past 100 episodes isn't that associations could adopt AI, but that when given accessible tools and clear value propositions, they adopted faster than anyone—including us—expected. Episode 1 us would be stunned! Episode 100 us is taking notes on what associations are building next. Episode 200 us? We'll probably be surprised again by how far associations have pushed beyond what we thought possible.

The transformation from spectator to participant is accelerating. By Episode 200, your association will be on one side of that divide or the other. Welcome to the participant era. The view from the stage is much better than from the seats.