UnTangled with Ben Childers: Be Curious and Experiment with AI

Last week’s UnTangled with Ben Childers, CEO and co-founder of Stratovation Partners, left me thinking about something really simple:  We don’t actually have to have all the answers before we start experimenting with AI.

That was one of the key takeaways from the in-person Cool/Scary AI Sh!t Meetups that Ben and his team have started convening. Folks are gathering in different cities across the US to talk about what they are learning, trying, and building. And it is exciting times!

He said that folks are diving in and finding new and interesting ways to use AI. And it isn’t about having the perfect plan in place before trying things out. In fact, if we wait until we think we have the perfect plan, the moment will have already passed. AI is moving too quickly for the old “freeze, rearrange, refreeze” style of adoption.

Instead, he suggests we pick some small, low-risk corners of our work and just start trying things.

• Hate your project management tool but have to use it? Maybe you try vibe coding a lightweight workaround that makes your life easier while still feeding the system.
• Dread writing up meeting notes? Let AI do the first messy draft, and you just clean it up.
• Wasting hours on scheduling? Offload it.

This is where leadership matters. Leaders don’t need to create a 50-page AI policy before their staff can even touch the tools. What they do need to do is set clear guardrails: here’s where it’s safe to experiment, and here’s where it isn’t. Protect the sensitive data, protect your donors, protect your community — but don’t block innovation in the everyday spaces where staff could save time and frustration.

Rethinking Risk

That’s also where rethinking risk comes in. Not every AI experiment carries the same weight. Building a personal to-do list that syncs with your main system? Pretty low risk. Uploading all your donor PII into a random chatbot? Hard pass. Risk isn’t binary, it’s a spectrum — and leaders should help their teams understand where the lines are.

AI Literacy Matters

And here’s another truth: AI literacy still matters. Even if your team isn’t coding or building prototypes, they need a basic understanding of what AI can and can’t do. They need training, practice, and the chance to play. Leaders should invest in making that learning accessible. The organizations that succeed will be the ones where staff feel confident — not just compliant. And your teams are already using it, whether you give them guidelines or not. So provide opportunities for learning and basic guardrails to ensure a baseline of safe behavior, and then let folks play.

Humans Will Always Be the Center of Your Work

The reality is this: AI will never replace the human side of nonprofit work — the caring, the listening, the relationship-building. But it can lighten the load of the systems that sit around that work. Marketing. Scheduling. Note-taking. Admin. The boring-but-necessary stuff that eats into your mission.

And if you’re willing to think outside the box, AI can even start to support pieces of service delivery itself.

• Scheduling food deliveries at a pantry.
• Analyzing housing and map data to optimize donation drop-offs.
• Speeding up patient intake.
• Tracking supply inventory automatically.

None of that replaces your mission. It just clears the path so your people can focus on the work only humans can do.

So my takeaway from last week’s episode? Lean in with a curiosity mindset. Put some loose guardrails in place, help your team build literacy, and then give them the freedom to test, play, and discover.

Watch the full episode here:

I would love to learn how your team is experimenting with AI to help streamline parts of your work, so if you have a great story to share, drop me a note!

Ready to get started learning more about AI? Let’s talk!