"Retention is the new growth."
- Meira Farber
- Mar 26
- 1 min read
Updated: 4 days ago
Allison Pickens, Former COO of Gainsight

The key to driving retention? It starts with asking the right questions during every client conversation. These moments are golden opportunities to uncover what truly matters to your customers and address challenges before they become problems. 🎯
Here are five great question categories that transform client calls into retention-building conversations:
1. Goal Alignment Questions
"What are your top priorities this quarter?" "How will you measure success with our solution?"
WHY: When you align with their objectives, you become indispensable to their success story.
2. Discovery Questions
"Walk me through what's working well and what isn't." "What obstacles stand between you and your desired outcomes?"
WHY: Early problem detection is your best defense against churn.
3. Partnership Questions
"What would make you look like a hero to your team?" "How can we become an extension of your success?"
WHY: Emotional investment creates stickiness that features alone can't match.
4. Future-State Questions
"Where do you see your team/company in 18 months?" "What emerging challenges are you preparing for?"
WHY: This positions you as a strategic partner, not just a vendor.
5. Value Realization Questions
"How has our solution impacted your day-to-day operations?" "What ROI metrics are most important to your leadership?"
WHY: Helping clients quantify your value makes renewal conversations easier.
Power Move:
End every call with: "What haven't we discussed that's on your mind?"
Remember:
Every question you ask is an investment in your client's success and your retention rates.
What question has given you the most valuable insights from your customers?
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