The Best Feedback Comes From The Toughest Rooms

I recently had one of the most energizing conversations in a while with someone long skeptical of AI in insurance. Their skepticism wasn't hostile, but rather stemmed from deep experience and an honest recognition of the gap between the promise of AI tools and their practical application. They've tested everything—offshore staffing, operating model shifts, emerging technologies—all with mixed results. This level of realism, especially from someone in the trenches of claims operations, is exactly the kind of perspective I value most.

It reminded me of Peter Drucker’s famous line: “The most important thing in communication is hearing what isn’t said.” True progress often comes not from the easy rooms where everyone nods along, but from the tough ones where people challenge, probe, and reveal blind spots.

‍

From Debate to Dialogue

What began as a frank back-and-forth slowly evolved into something much more constructive. We openly discussed the challenges of working with both tech-driven and human-powered vendors, and how difficult it can be to find solutions that truly work in the real world. It wasn't a debate, but two people comparing notes, questioning assumptions, and striving to understand each other's viewpoints. Through this process, something shifted.

Building With, Not For‍

This experience aligns closely with the design thinking philosophy popularized by IDEO’s David Kelley: build solutions with people, not for them.I shared my approach to product development: not by pushing a finished solution, but by building iteratively, guided by expert input and real feedback loops. When you build with people, not for them, you foster trust. This is where transparency comes in: being honest about what a tool can and cannot do, and explaining the reasoning behind decisions. This kind of openness transforms skeptics into collaborators.

Turning Skeptics into Partners
‍
By the end of our conversation, what started as a cautious exchange concluded with alignment and shared optimism. We didn't solve everything, but we found a way to move forward together. To me, that's the core of driving AI adoption in this industry. It's not about flashy demos or bold claims; it's about trust, honesty, and demonstrating that people's lived experiences can shape something better.

As Steve Jobs once said, “You’ve got to start with the customer experience and work backwards to the technology.” And in my experience, the toughest rooms — the ones with the hardest questions — are where the best ideas ultimately take shape.