310: Bringing Cohesion To Chaos; with Colin Flanigan

Send us Fan Mail

Chaos in customer support rarely starts as chaos. It starts as “organic” growth, a few heroic workarounds, a helpful engineer jumping into Zendesk, or a fast acquisition that bolts on a new product and a new team without a shared operating system. Then the outcomes get unpredictable: escalations drag, customers hear different answers, and everyone feels busy while nothing feels steady. We dig into how to bring cohesion back without killing the good parts that made the team successful in the first place.

Colin Flanigan joins me to unpack what he does in technical support leadership across B2B SaaS, including the messy reality of joining after rapid change. We talk about the first weeks on the job as a blend of journalist and analyst: running a genuine listening tour, collecting complaints as signals, building a friction map, and then validating the story with real support metrics. From there, we explore how to use proven frameworks (not rigid prescriptions), where bespoke work matters most (especially voice of the customer programs), and why many “technical” problems are actually broken communication systems across teams.

We also go deep on the human side of change management: how to earn trust even when people do not fully agree, how to recruit champions from the people who care most about specific pain points, and why early wins in the first 60 to 90 days matter. We finish with practical leadership tactics like disagree-and-commit, time-boxed experiments, not optimizing for edge cases, and setting clear boundaries between support, engineering, and product so goodwill does not turn into resentment.

If you want sharper support operations, stronger cross-functional alignment, and more predictable customer experience outcomes, listen now. Subscribe, share this with a support leader who is cleaning up chaos, and leave a review with the one boundary you wish your org would clarify.

Support the show