A CSM team told me this week they were worried about coming across as annoying.
Every time they asked a customer for data access, or a response on something agreed, it felt like nagging. They were that person constantly emailing, "just following up!" They wanted to know how to ask for these things without being a pest.
Here's the answer: holding a customer accountable to their own success isn't pestering. But it only stops feeling like pestering once success has actually been defined. And I mean very well-defined: strategic, sizable, measurable, time-bound. Without that, every ask really is just noise. With that, the ask has a reason to exist that both sides recognize.
Think about a general contractor. When they call asking you to pick the tile by Friday, they're not being pushy. They're protecting the move-in date you both agreed to. And honestly, most of us have been on the other side of a project that dragged on for months with no one holding anyone to anything. So when a contractor actually does chase you for a decision, tied to a real date, it's a pleasant surprise. You don't resent it. You appreciate that someone is looking out for your interests.
A physical therapist after surgery is a clean version of this. There's a defined outcome: full range of motion by week eight. And the PT checks whether you did your home exercises. If you skipped them, they'll tell you plainly that missing sessions now means less mobility later, maybe permanently. That's not a scolding. It's the truth about the agreed outcome. Nobody accuses their PT of pestering them.
Notice what these have in common. Neither relationship runs on vague goodwill or "let's stay in touch." Each starts with an agreed, specific, meaningful outcome: a move-in date, a range-of-motion milestone.
The accountability exists because the outcome exists.
This is where most CS teams get stuck. They want the accountability posture of a contractor or a PT, but they never did the work of agreeing on a strategic, sizeable, measurable outcome with the customer up front. So every ask feels invented, because in a sense it is. There's nothing underneath it except the CSM feeling the pressure of adoption and usage.
Fix the front end, and the back end takes care of itself. Define success early (real success, not "increase adoption" or "improve engagement") and suddenly asking for data access or a decision isn't you pestering them. It's you doing your job.
So if your team feels like they're bothering customers, don't coach them on tone. Go back and check whether success was ever actually defined. That's usually where the discomfort is coming from.