The Deeper Questions digitalNow 2025 Is Really Asking

I'm sitting here on Day 3 of digitalNow 2025 in Chicago. Over the past few days, we've seen incredible sessions on implementation, infrastructure, and culture. Earlier this week, we analyzed the schedule and shared two major insights about where associations are with AI: moving beyond pilots and culture beating tools every time.

But beneath those practical insights, the conference agenda has been revealing deeper, more existential questions. Here are two more insights that go beyond tactics to ask: what is the future role of associations in an AI-driven world?

Insight #3: The Trust Crisis Is Real

One question has come up repeatedly across sessions this week: are associations still relevant when members can get instant answers from ChatGPT? When they can find expert content on YouTube? When influencers in their profession are building communities that compete directly with associations for attention and loyalty?

The information landscape has fundamentally changed. Associations used to be aggregators and gatekeepers when information was scarce. Now information is abundant, often free, and instantly accessible. The value proposition associations relied on for decades no longer works the same way.

Marcus Sheridan Set the Stage on Day 1

Marcus Sheridan's opening keynote tackled this head-on with "Becoming the Undisputed Voice of Trust in Your Space." Not a voice. THE voice.

His talk focused on trust in an era where attention is scarce, patience is thin, and trust is everything. The hard question he posed: how do associations evolve to match the expectations of today's radically informed, self-educating, impatient audience?

Why This Matters

Your members can:

• Google anything
• Ask ChatGPT anything
• Find influencers on YouTube teaching them about their profession

So why would they come to you?

Multiple sessions this week picked up this thread. "What Your Members Wish You Knew: Rethinking Tech to Build Trust, Spark Belonging, and Drive Growth" from Forj and AANA. Bryan Kelly's longevity economy session explicitly about creating experiences grounded in clarity, trust, and respect. And beneath every implementation session was the underlying tension: will this make us more valuable to members, or can AI do this cheaper and faster?

What Makes This a Crisis

This isn't about having slightly less engagement. It's about the fundamental value proposition of associations being questioned.

Information used to be scarce. Now information is abundant and the question becomes: what's your unique value?

Associations risk becoming episodic, where members only interact when they need CEUs or to renew membership, not as ongoing daily relevant organizations. AI is commoditizing not just information, but knowledge itself. The ability to solve problems, develop strategies, apply information to real situations.

And then there are the influencers. In every profession, people are building their own audiences and communities, in direct competition with associations for member attention and loyalty.

What This Means for Your Association

You can't compete on information access anymore. You can't compete on convenience - AI is faster. You can't compete on cost - free is hard to beat.

You CAN compete on:

• Trust
• Community
• Credibility
• Curation
• Application
• Connection

Marcus Sheridan's question matters: how do you become THE trusted voice, not just a voice among many?

Insight #4: The Wild Cards Tell a Story

Not every session at digitalNow this week fit neatly into categories like "implementation best practices" or "building AI infrastructure." Some of the most interesting programming ventured into unexpected territory: dolphin communication research, mindfulness practice, the parallels between human brains and artificial intelligence.

These sessions revealed something important about how association leaders are thinking about AI. Beyond the tactical questions about which tools to use and how to deploy them, there's recognition that AI transformation touches deeper questions about intelligence, consciousness, and what makes us human.

The wild card sessions mattered because they showed curiosity and depth. They signaled that this work isn't just about efficiency gains and cost savings.

Dr. Denise Herzing - Using AI to Study Dolphin Communication

On Day 2, Dr. Denise Herzing presented on using machine learning to find language patterns and complexity in dolphin sounds. She discussed custom programs like UHURA, Video/Sound AI interfaces, and DolphinGemma (a collaboration with Georgia Tech and Google DeepMind). She was recently selected to the TIME AI 100.

What this session says: AI isn't just about operational efficiency or member services. It's about expanding what's possible in research and understanding. AI can help us understand intelligence itself, not just automate tasks.

Dr. Param Dedhia & Thomas Altman - The Brain and AI

Also on Day 2, this keynote explored the surprising parallels between human brains and artificial intelligence and the critical gaps that separate them. The session examined how neuroplasticity, bias, and attention shape both biological and artificial systems.

What made this keynote compelling was watching how technology mirrors science. The same patterns that govern how our brains learn, adapt, and make decisions show up in AI systems. But understanding those parallels also helps us see what's fundamentally different, like the ways human cognition remains distinct from even the most advanced AI.

The session was about understanding ourselves through the lens of AI. What makes human thinking unique? Where do our cognitive strengths and weaknesses overlap with AI's? How can we use that knowledge to work better with these systems?

Dr. Param Dedhia - Mindfulness and AI

Day 2 included a quick 15-minute interactive activity on the power of taking a pause in a world moving at breakneck speed. How mindfulness can sharpen focus, boost performance, and turn AI from a passive tool into a powerful partner.

The human element isn't just about change management. It's about how we show up, how we think, how we pay attention. In a conference full of "move faster with AI," here was a session saying "slow down and be present."

What These Wild Cards Reveal

AI transformation isn't just about ROI and productivity gains. There's recognition that this is deeply human work.

It's about curiosity: dolphin communication research. It's about consciousness: mindfulness practice. It's about understanding intelligence itself: brain and AI parallels.

The technology is just the tool. The real work is understanding ourselves and how we engage with intelligence, artificial or otherwise.

What This Means for Your Association

Don't lose sight of the bigger picture while implementing AI. The work you're doing with AI touches on fundamental questions about knowledge, learning, community, and human connection.

Your AI strategy should make space for curiosity, not just efficiency. The associations that thrive won't just be the ones with the best chatbots. They'll be the ones that understand what makes human expertise, judgment, and connection valuable in an AI world.

What These Insights Tell Us Together

Earlier this week, we covered the tactical insights: moving beyond pilots and building AI culture. But these two deeper insights complete the picture.

Insight #3 asks: what's your unique value when AI can do what you used to do?

Insight #4 suggests: your value is in the deeply human work. Curiosity, consciousness, connection, trust, understanding.

Members won't come to you just for information. AI has that. They'll come for what AI can't provide: trusted human judgment, curated expertise, meaningful community, deep understanding. The wild card sessions showed what that looks like. Exploring big questions. Slowing down to be present. Understanding intelligence itself. This is the work AI can't replicate.

Wrapping Up

Sitting here on Day 3 of digitalNow 2025, wrapping up an incredible few days in Chicago. We've seen sessions on predictive modeling, AI deployments, content foundations, and innovation cultures.

But the conference has been asking deeper questions the whole time. Can associations remain relevant when AI provides instant answers? What makes human expertise, judgment, and community valuable in an AI world?

Based on the sessions, the speakers, and the conversations happening here, association leaders are grappling with both questions.

The tactical work matters. But the existential work might matter more. Trust. Meaning. Human connection. The associations that figure out both will be the ones that thrive.

It's been a great few days! And these are the questions we're taking home.