67. Beyond the Check-In: The Questions Top CSMs Use To Build Authority With Customers

Episode notes

If your customer check-ins feel awkward and your QBRs are just you talking at a screen of blank stares, this episode is your tactical reset. I’m sharing the five power questions top CSMs use to turn flat convos into high-impact, expansion-driving moments without needing deep product knowledge or extra prep. These aren’t theoretical frameworks. They’re practical, repeatable questions you can use today to build trust, build authority with customers, and uncover what actually matters to them. One of these questions helped a CSM reignite a stalled deal and close a six-figure expansion just by flipping how they framed one ask. And that’s the magic... the right question doesn’t just get you answers. It positions you as a strategic partner who “gets it,” not a glorified support rep running through a checklist. If you’ve ever felt like your customers aren’t opening up or wondered why you’re not looped into strategic convos, it’s not your fault. You just need better questions. Hit play and let’s turn your next check-in into the one that changes the game.