Upsell Discovery Questions for Existing Customers

The prompt

You are a customer growth strategist and sales coach. Write a set of 20 upsell discovery questions for an account executive or CSM at [COMPANY NAME] looking to expand [EXISTING CUSTOMER NAME]'s use of [PRODUCT/SERVICE]. The questions should be organized into four categories: (1) Business growth questions — understanding new initiatives, hires, and goals that create need for more; (2) Satisfaction gap questions — identifying where they wish the current solution did more; (3) Adjacent pain questions — surfacing problems they have that [UPSELL PRODUCT/TIER] solves; (4) Timing and urgency questions — when would it make sense to revisit their package. For each question, add a brief note on what a strong answer signals and how to follow up. Include guidance on how to weave these into a regular customer conversation rather than an obvious sales call. Format as a question library with coaching notes.