Relationship-oriented Customer Success folks tend to hold a lot internally. They process before they speak, they're careful about what they surface and when, and they've usually already thought through all of the angles of a problem before they bring it to you. This quality makes them exceptional in the room with a customer, and conversely it can lead to underestimating them in a team setting.
It’s easy to feel connected to the person who fills every 1:1 with observations and opinions. There's always something to respond to and plenty of nice, accessible threads to pull. But volume in a 1:1 isn't the same thing as signal, and you’re working with a partial picture if your read on how the team is doing primarily comes from your most vocal people.
Getting a real read on your team is less about extracting information and more about creating the conditions where people who don't naturally broadcast feel like it's worth the effort and risk. Figuring out what those conditions look like for each person on your team is some of the most important work you'll do as a CS leader, whether that's asking a more specific question instead of an open one, or just demonstrating that the last thing they told you actually went somewhere. If you don’t already read Lara Hogan, one of my longtime favorite writers and coaches on leadership in technical environments, check out the really great resources for giving and getting more in your 1:1s she’s made available for free on her site.
Leaders with the most complete picture of their teams have usually figured out that the people least likely to volunteer information are just as important to hear from as the ones who always have something to say.
Book a consultation for CS Leader Lab for help connecting with the more reticent folks on your team.