Day 2 of digitalNow 2025 just wrapped in Chicago. Over the past two days, we've seen incredible sessions from association practitioners, AI experts, and thought leaders. Sessions on AI agents and collective intelligence. Keynotes about trust and the longevity economy. Panels on building innovation cultures. Workshops on predictive modeling and content foundations.
With so many sessions across three days, we wanted to step back and look at what the conference agenda itself reveals about where associations are with AI. So we fed the entire schedule to AI and asked: what are the dominant themes and insights?
Two major findings emerged: First, associations have moved beyond pilots. The dominant question is no longer "should we try AI?" but "how do we make it work at scale?" Second, culture beats tools every time. The sessions focused on building innovation environments outnumber the purely technical ones.
Here's what each insight reveals about where associations really are with AI right now.
The shift in questions tells you everything. We're no longer asking "should we try AI?" The new question driving sessions at digitalNow: "how do we actually make AI work at scale?"
The evidence shows up clearly in the schedule. We counted eight implementation studies - practitioners from associations sharing what they actually did over the past 18 months. Not theoretical frameworks. Real deployment stories with real outcomes.
ICBA is rebuilding five websites using member behavior data and continuous feedback loops. They're applying proven e-commerce testing methods (conversion funnel analysis, user journey mapping, A/B testing) to help members discover content more easily.
The Northern Virginia Association of Realtors re-architected their web and mobile content to become "AI-ready." Their team focused on taxonomy, metadata, and ingestion pipelines so large language models can understand the nuance of their resources. They built AI-powered site search that speaks the member's language and a "Latest for You" feed that personalizes news and events. Their insight: lean budgets and small staffs can still deliver features with release cycles measured in weeks, not years.
The American Academy of Pediatrics moved beyond AI hype to build something with actual member value. They took an "agent-first" mindset, solving specific business problems rather than adopting technology for its own sake. Their session covers how they identified meaningful use cases, built solutions that enhance member engagement, and defined metrics to measure success.
AGU's Thad Lurie is presenting 18 months of actual AI deployments. Not the applications themselves, but the specific business outcomes and impacts each generated. The session is designed for association executives with only passing knowledge of AI, focusing on business results over technical solutions.
John Huisman's session title says it directly: "From Pilots to Performance." After all the proof-of-concepts, what separates organizations achieving tangible outcomes from those still searching for their first win?
The answer showing up across digitalNow sessions: you can't just slap ChatGPT on your website and call it transformation. You need proper foundations.
Ian Andrews from Groq is covering inference technologies, energy-efficient AI architectures, and emerging regulatory frameworks. This is infrastructure-level thinking. The NVAR and Accella session digs into content foundations - the essential structuring decisions you need to make now, the minimal technical stack required, and repeatable processes for spinning up AI pilots that actually work.
The technical depth required to move beyond pilots is real. Success comes from understanding what's happening under the hood, not just which tools to buy.
If you're still in the "let's try ChatGPT and see what happens" phase, you're behind where the field is moving. The focus needs to shift to foundations and frameworks. Implementation requires proper data architecture, content structure, and clear understanding of how AI systems actually process your information.
The associations presenting at digitalNow spent 18 months figuring this out. They're sharing what worked, what didn't, and what their members gained. The work ahead isn't about experimentation anymore. It's about building systems that deliver measurable value.
Here's what surprised us in the schedule analysis: "culture" appeared four times as an explicit theme, but it's woven through nearly every session. And Conor Grennan's keynote with his son Finn states it directly - culture, not tools, determines AI success.
Multiple sessions at digitalNow are dedicated entirely to building the right environment for AI adoption. Not how to use the technology. How to create organizations where the technology can actually take root.
The "Beyond the Bot" panel brings together leaders from AANA, AACSB, and MDRT to share how they created environments where innovation thrives. They're discussing Shark Tank-style contests, structured evaluation frameworks, and what they call "safe to try" environments. Each organization empowered staff to experiment, validate ideas, and tie AI initiatives directly to strategy and member value.
The Morton Arboretum created an "AI Explorers" program - judgment-free, collaborative spaces for staff to learn and experiment with tools like ChatGPT, Claude, and Midjourney. Their insight: demystifying AI allows non-technical people to see themselves as valuable contributors to technology strategy. When you anchor conversations in mission, values, and strategic vision while emphasizing practical application, you bridge the gap between enthusiasts and skeptics.
These aren't feel-good initiatives. They're practical frameworks for getting organizations to actually use AI rather than talk about it.
Conor and Finn Grennan's father-son keynote brought two generational perspectives to AI adoption. Their central message matters for every association: how do we create a generation that doesn't just know how to use AI, but knows how to think with it?
Bryan Kelly's session on the longevity economy adds another dimension. One in three Americans will soon be over 50. We're entering what experts call the "Super Age." Associations need to serve both older professionals and the generation entering the workforce. That's a massive spectrum for AI adoption - from people who remember life before email to people who've never known a world without smartphones.
Building AI culture means building critical thinkers across all age groups and technical backgrounds. The challenge isn't just training people on tools. It's creating environments where different perspectives on technology can coexist and strengthen each other.
What if Sam Altman or Dario Amodei walked into your association tomorrow with plans for a complete AI overhaul? Would they succeed?
The answer probably depends less on their technical expertise and more on whether your organization has the culture to support what they'd want to build. If you don't have environments that support innovation, experimentation, and "safe to try" spaces, even the world's leading AI experts would struggle to transform your association.
Technology alone can't overcome cultural resistance. And building innovative culture isn't a finish line you cross. It's an ongoing practice showing up in weekly meetings, Slack channels where people share experiments, and leadership responses when AI initiatives don't work out as planned.
AI transformation is more change management than technology implementation. The technical part (choosing tools, building systems, deploying applications) is actually the easier part. The hard part is getting your organization to think differently about work, experimentation, and failure.
Start with small wins:
These small cultural practices matter more than which AI platform you choose.
Focus on psychological safety before technical training. Create environments where curiosity matters more than coding skills. Build bridges between enthusiasts pushing for change and skeptics raising valid concerns about quality, accuracy, and member experience.
We are in a phase of "AI adolescence." We're past the wonder and experimentation of AI childhood - the phase where associations were just playing with ChatGPT to see what it could do. But we haven't reached maturity yet. That would look like seamless AI integration, proven ROI across organizations, and full cultural adoption.
We're stuck in the awkward middle. We know what we want to do. We've run pilots that show promise. But actually getting there - building the infrastructure, changing the culture, scaling what works - that's where most associations are struggling right now.
And that's exactly what makes these two insights powerful together:
Technical foundations plus cultural readiness equals actual transformation. Miss either piece and you stay stuck in pilot purgatory.
digitalNow 2025's schedule is a snapshot of where associations are with AI right now. And the story it tells is clear: we're in the building phase, not the wondering phase.
The work ahead requires both technical depth and cultural change. Infrastructure and innovation environments. Proper foundations and psychological safety. The hard technical work of taxonomy and metadata alongside the human work of creating spaces where people feel safe to experiment.
Based on what's happening in Chicago this week, association leaders are ready for both. The sessions are packed with practitioners sharing real implementation stories. The conversations are focused on what it actually takes to make AI work at scale. And the themes emerging from the schedule - beyond pilots, culture over tools - point to an industry moving through adolescence and toward maturity.