Three Days in Chicago: A Look Back at Support Driven Expo 2026

There was a lot to talk about at Support Driven Expo Chicago.

AI came up in sessions, conversations, and probably more hallway chats than anyone could count. But what stood out wasn't just how much people were talking about AI. It was what they were trying to figure out.

The question wasn't really “Should we be using AI?” anymore. It was more like, “How do we actually make this work?”

Much of that came down to some pretty familiar things: good documentation, reliable information, clear processes, and making sure teams can find the information they need. If your help center is full of outdated articles, conflicting instructions, or information spread across different places, adding another tool won't solve the underlying problem. As support teams use AI more, keeping their knowledge accurate and up to date becomes even more important.

The work is changing, but the basics still matter

There was also a lot of discussion about what happens to support teams as AI takes on more of the simpler work.

People talked about spending less time answering repetitive questions and more time on complicated problems, broken workflows, investigations, and the conversations that still need human judgment.

One attendee put it simply: whether support is handled by people, AI, or both, the basics haven't changed. Good knowledge management, breaking down information silos, and thoughtful planning still lead to better-informed, happier customers.

And then there were the conversations that had nothing to do with a slide deck.

People met for the first time, caught up with old connections, continued conversations from sessions over coffee, and talked about what was actually happening on their teams.

Those moments were a big part of the Expo too.

One attendee left with a list of ideas they were actually going to work through with their team. Others talked about leaving with new questions, new connections, and a better sense of what other support organizations are figuring out right now.

Maybe that's the best way to describe Expo Chicago. Nobody left with everything figured out, and that wasn't really the point. People left with a few things to try, a few problems to think about differently, and the reminder that they're not the only ones working through the challenges support teams are facing.

That's the part you don't always get from watching a session online. The hallway conversations, quick introductions, and time spent over coffee can sometimes be just as useful as the session you came to see. You might realize that someone else is dealing with the exact same problem, or leave with an idea you hadn't considered before.

You have to be in the room for those.

And that's why we're already looking forward to the next one.

If you couldn't make it this time, there's always another conversation ahead. Join our events newsletter to be the first to hear about upcoming Support Driven events.