Love Your Curmudgeon: Embracing Your Least Likely Partner In Transformation

Dan Schommer and I recorded this session on January 21, 2025, as part of Dawn Stevens' Let's Talk Tech Docs webinar series.

Every content team has a curmudgeon. They're usually the most tenured person in the room, the one who asks the hard questions nobody else will ask, and the one most likely to be dismissed as obstructionist when a new initiative comes through. That dismissal is a mistake. The curmudgeon's resistance is almost always rooted in institutional knowledge — they've watched similar initiatives fail, they understand the real cost of the disruption, and they're protecting the team in the only way they know how.

In this session, Dan and I work through who the curmudgeon is, what actually motivates their skepticism, and the specific strategies that move them from obstacle to ally. This isn't about managing difficult people. It's about recognizing that the person most likely to derail your project is also the person most likely to save it — if you bring them in early and take their concerns seriously.

If your team is navigating a tool migration, a structured authoring rollout, or any significant shift in how content gets produced, the friction you're experiencing from resistant colleagues is a signal, not just a problem to work around.

Watch the recording on demand.

When a content change initiative runs into resistance, the instinct is usually to push harder or work around the people who aren't on board. In my experience, that approach costs more time than it saves — and it leaves the institutional knowledge on the sideline precisely when you need it most. If you're trying to figure out how to build a change strategy that accounts for the real dynamics on your team, I'm glad to talk through what that looks like.

Book a free discovery call today.

This webinar was part of Let's Talk Tech Docs, hosted by Dawn Stevens of Comtech Services, co-sponsored by Intuitive Stack, CIDM, Heretto, and The Content Wrangler. Co-presenter: Dan Schommer.

The written companion goes deeper on the curmudgeon profile and engagement strategies than the webinar format allows.

The ConVEx 2025 session covers the other side of this dynamic — four scenarios where agents of change and their teams talk past each other.