Sidecar Blog

The Most Exciting Thing I’ve Learned About AI This Year

Written by Sheri Jacobs | Jun 2, 2025 2:00:26 PM

A few months ago, I facilitated a strategy session for an association trying to reach younger members. They’d been trying different tactics for years, but nothing seemed to move the needle in a meaningful way.

This time, we did something different.

Instead of starting with what had worked in the past, we gave the challenge to a cross-functional team, including an early-career staff member and frontline staff, and let them experiment with an AI tool to generate new ideas.

One staffer asked the AI: “If our goal was to capture the attention of a 27-year-old who’s never heard of us, what kind of message would stop them mid-scroll on TikTok or Instagram?”

The results? Creative ideas we could customize in a campaign:

  • The, “Wait, That’s Me” Hook – Ever feel like you’re too smart to feel this stuck in your career?
  • The “I Didn’t Know That” Hook – Only 4% of people do this one thing – and they’re the ones who get promoted, funded, and followed.
  • The “I Call BS” Hook (Disruption + Truth) - Networking doesn’t build your career. This does. And no one’s talking about it.
  • The “WTF Just Happened” Hook – This idea was dismissed!

Being more creative in our prompts led to a richer discussion around how to capture the attention of a hard-to-reach audience. This led to an A/B test across three platforms, using a tone and format the organization had never tried before.

And it worked.

AI didn’t just give them content – it helped them define the real boundaries of where they could play and be creative.

I’m not sure if it is the most exciting thing I learned about AI this year, but watching a team become more creative because they defined the boundaries and then used a tool to spark their imagination – that ranks at the top of the list. AI creates just enough distance from our assumptions to unlock new ideas.

And in a field like ours - where tradition runs deep and change can feel risky - that kind of nudge is priceless.

Too often in associations, innovation stalls not because of a lack of ideas, but because of the invisible boundaries we place around them. We default to what’s familiar. We rely on the same voices in the room. We let bureaucracy or fear of failure box us in.

But AI, when used intentionally, breaks that pattern.

When a tool gives every person at the table the power to generate, test, and refine bold ideas, it doesn’t just democratize creativity - it accelerates it.

AI is making us more human. Because when we’re freed from the repetitive, we can spend more time listening, learning, and leading.

Here’s what that looks like:

1. Let AI redraw the lines, not erase them.

Constraints are not the enemy of innovation - they’re the fuel. Great ideas rarely come from unlimited options. They come from specific challenges, clear boundaries, and the courage to explore within them. AI gives you a new playground to explore, but you still have to set the rules. Want better member engagement? Ask AI: What if we removed 80% of what we currently do - what would we keep?

2. Use AI to amplify unheard voices.

I’ve seen early careerists spark board-level conversations because AI made their ideas visible and viable. Frontline staff can now test assumptions and model ideas that once required consultants, budget, or permission. When everyone has a seat at the innovation table, the ideas get better - and so does the culture.

3. Make more attempts, not perfect plans.

AI lowers the cost of trying. It lets you run through 20 versions of an idea in the time it used to take to outline one. That’s the real opportunity: more shots on goal. If you wait for perfect, you’ll miss what’s possible. And in this moment of generational shift, digital disruption, and evolving member expectations, standing still is the riskiest move of all.

What excites me most about AI is that it enables us to ask better questions.

  • It doesn’t care how many years we’ve been doing something a certain way.
  • It doesn’t worry about whether the board will push back.
  • It doesn’t carry our fear of failure or our fatigue from past missteps.

It simply suggests. It nudges. It opens the door.

And as leaders, it’s our job to walk through it.

AI isn’t going to replace the strategic thinking, empathy, and judgment that make associations special. But it will challenge us to lead differently. To listen differently. To take more chances. And to expand the boundaries - mental, structural, and cultural - that may be holding us back.

So, what’s the most exciting thing I’ve learned about AI this year?

That it doesn’t just help us do more. It helps us take more shots.

And in a sector defined by purpose, people, and progress, that’s the kind of shift we’ve been waiting for.

Sheri Jacobs is a global keynote speaker, author, and CEO of Avenue M Group. When she’s not helping organizations innovate and lead through uncertainty, she’s photographing wildlife on all seven continents.

You can reach Sheri at jacobs@avenuemgroup.com or visit her website at www.avenuemgroup.com or www.sherijacobs.com

LinkedIn: https://www.linkedin.com/in/sherijacobs/