Before You Add AI, Ask a Better Question

Aug 30, 2026  /  Bill Ryan

Every time I see AI fall flat, it’s because we tried to layer it on top of old habits instead of questioning them.

USDLA Pinwheel Logo

I’ve been watching, and helping, a lot of organizations as they race to implement AI and I am getting more concerned about how slowly we’re nurturing the human skills, the business behaviors, that make those implementations actually work. The more I watch teams adopt new tools, the more convinced I am that curiosity isn’t just a “nice to have.” It’s the skill that determines whether AI becomes a force multiplier or just another layer of process sitting on top of existing processes, aka “old habits”.

This week I was having a conversation with a team that was exploring implementing an AI platform. I’m friends with the CTO and as they talked about the various tools, ways to train the staff, ideas on pilot projects and teams to try these new AI workflows I leaned over and to see if I could ask a question, a simple, curious question: “What problem are you really trying to solve here?”

That question opened the door. Suddenly people were talking about friction points, outdated steps, and opportunities to streamline. They weren’t trying to force the new tool into the old processes; I heard words like “what if” and “why do we do it that way”. That’s when the energy shifted. Curiosity created momentum and engaged people with each other to explore outside of the “lines”.

What this looks like in a real workday

Here are a few small, immediate actions that help bring more curiosity in front of your AI tools and they take minutes, not hours:

  1. Ask one “problem-first” question before you open the tool. Something like: “What’s the real bottleneck here?” or “What outcome do we want to improve?”
  2. Invite one colleague into the conversation. Curiosity grows when it’s shared. Ask: “Want to try this with me?”
  3. Run a tiny experiment. Not a pilot. Not a project. A 10-minute test.
    “What happens if we remove this step?”
    “What if we let the AI draft the first 20% instead of the last 20%?”
  4. Name one workflow that feels heavier than it should. Then ask: “If we were starting from scratch, would we design it this way?”

These micro-moves broaden and build capability not just for individuals, but for the whole team. When people feel invited, and supported, to explore, experiment, and question, they stop treating AI as a threat or a mandate. They start treating it as a partner.

Your turn

I’d love to hear how curiosity is showing up in your work. Where have you seen a question unlock a better workflow, a better idea, or a better outcome?

If you’re working through how to bring more human-centered skills into your AI adoption efforts, I can help whether it’s defining the business behaviors we use to perform successfully, refining workflows, or building team capability in the flow of work. Let’s make some time to talk.

profile

Bill Ryan

Bridging Distance, Building Excellence – As founder and CEO of Ryan Consulting, I transform how organizations thrive in remote and virtual environments.

For over 25 years, I’ve been fascinated by one question: How do we create extraordinary connection and performance when teams aren’t in the same room? This question has guided my career helping organizations harness the full potential of their distributed workforce.

My approach is refreshingly practical. I align what I call the 3P’s—Purpose, People, and Process—creating frameworks where remote teams don’t just function, they flourish. In today’s landscape of rapid change, this alignment isn’t just helpful—it’s your competitive edge.

Working together, we’ll craft solutions precisely calibrated to your organization’s unique challenges. Whether through customized workshops on performance support, process refinement, mobile solutions, or organizational effectiveness, I bring proven strategies that deliver measurable results.

My greatest satisfaction comes from watching leaders, teams, and individuals discover they can collaborate more effectively across distance than they ever thought possible. In a world of constant change, that’s not just good business—it’s transformational.

Ready to reimagine what your remote workforce can achieve? Let’s connect.