You asked what was not working, they said “honestly, onboarding is a mess,” and your next line was “got it, and how big is the team?”
Try this on your next call
“Onboarding’s a mess. Say more about that. Where does it actually break down?”
The first answer is rarely the real one. When someone hands you a live problem and you move straight to the next question on your list, they learn this is a checklist and stop volunteering the useful part. One good follow-up on the thing they clearly care about is where the real need finally comes out.











