75 B2B Sales Discovery Questions That Close Deals

Discovery is not an interrogation; it is a process of mutual diagnosis. Yet, too many reps fall into the trap of asking surface-level questions ("What is your budget?") before earning the right to ask them. The result? Prospects disengage, and deals stall.

To convert, you need to peel back the layers of the "Job to be Done." But remembering the right question for every unique scenario is impossible under pressure. This guide provides the ultimate list of questions, but more importantly, it explains why a Living Playbook is the only way to deploy them effectively.

Key takeaways

• Discovery is nonlinear. You don't ask questions in a perfect 1-to-10 order. You must adapt to where the buyer is in their journey. Gartner – The B2B Buying Journey 2025
• Top performers ask more. Data shows that successful discovery calls often involve 11–14 engaging questions, compared to fewer in lost deals. (Industry Benchmarks – 2025 Sales Discovery Data)
• Cognitive load kills curiosity. When reps are stressed about "what to say next," they talk too much and listen less. Real-time prompts free them to truly listen. (Industry Benchmarks – Talk-to-Listen Ratio in Sales Calls)
• Real-time AI boosts impact. In-flow suggestions improve outcome quality by up to 15% in knowledge work, directly applicable to dynamic discovery questioning. Bain & Company – AI Transforming Productivity in Sales 2025

Table of contents

• The Problem: Interrogation vs. Insight
• Phase 1: Rapport & Situation Questions
• Phase 2: Problem & Pain Questions
• Phase 3: Impact & ROI Questions
• Phase 4: Buying Process & Authority
• Phase 5: Role-Specific Questions (CEO, CTO, Managers)
• Why memorization fails
• How Nomi fits

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The Problem: Interrogation vs. Insight

A bad discovery call feels like a survey. A great discovery call feels like therapy for the business. The difference lies in Insight-Led Discovery. Instead of asking "What keeps you up at night?" (which is lazy), you ask questions that help the buyer see a problem they didn't know they had.

For a deeper dive on structuring these calls, read our guide on discovery calls that convert.

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Phase 1: Rapport & Situation Questions

Goal: Establish context without boring the prospect.

1. "I noticed you recently expanded into [Region]. How has that shifted your priorities?"
2. "What sparked your search for a solution like this right now?"
3. "Walk me through your current process for [Task]."
4. "What tools are you currently using to handle [Challenge]?"
5. "How big is the team responsible for [Function]?"
6. "What were the main goals set for your department this quarter?"
7. "I saw your post about [Topic] on LinkedIn—how is that playing out internally?"
8. "Who else interacts with this workflow on a daily basis?"
9. "How long have you been trying to solve this manually?"
10. "What is the biggest bottleneck in your current stack?"

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Phase 2: Problem & Pain Questions

Goal: Identify the Gap between where they are and where they want to be.

11. "What happens if you don't solve this problem by the end of the year?"
12. "On a scale of 1 to 10, how urgent is this issue compared to other initiatives?"
13. "What is the most frustrating part of your team’s day regarding [Process]?"
14. "Have you tried to fix this before? Why didn't it work?"
15. "Does this issue impact customer churn or employee retention?"
16. "How much time is your team losing on [Task] every week?"
17. "Is this problem preventing you from hitting your revenue targets?"
18. "What is the cost of doing nothing?"
19. "Are you worried about compliance/security risks if this continues?"
20. "If you could wave a magic wand and fix one thing about this process, what would it be?"

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Phase 3: Impact & ROI Questions

Goal: Quantify the pain to justify the investment. This is critical for value selling.

21. "If we solved this, what would you do with the extra [Time/Money]?"
22. "How would fixing this impact your personal KPIs?"
23. "What does a 'home run' look like for you six months post-implementation?"
24. "Can you estimate the budget currently wasted on inefficient workflows?"
25. "How will you measure the success of this partnership?"
26. "What metric does your CFO care about most regarding this project?"
27. "If we can improve [Metric] by X%, what does that mean for the business?"
28. "Who looks like a hero if this project succeeds?"
29. "What is the ripple effect of this problem on other departments?"
30. "How does this align with your company’s 2025 strategic vision?"

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Phase 4: Buying Process & Authority

Goal: Map the buying group and avoid last-minute blockers.

31. "Who else needs to weigh in on this decision?"
32. "Walk me through the last time you purchased software like this."
33. "Do you have a budget allocated, or do we need to build a business case together?"
34. "What legal or security reviews do we need to clear?"
35. "If we come to an agreement, what is your ideal go-live date?"
36. "Is there anyone who might be skeptical about this change?"
37. "What criteria will you use to choose between us and [Competitor]?"
38. "Do we need to get on the calendar for the procurement team now?"
39. "What is the 'deal breaker' feature for your technical team?"
40. "How can I help you sell this to your boss?"

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Phase 5: Role-Specific Questions (CEO, CTO, Managers)

Different stakeholders care about different outcomes. Use these to tailor your approach and complete your arsenal of 75 questions.

For the CEO / Founder: 41. "How does this initiative support your exit strategy or next fundraising round?" 42. "What is the one risk that keeps you up at night regarding this project?" 43. "How do you see this changing your company culture?" 44. "If we hit our targets, where does this put you against [Competitor]?" 45. "What legacy systems are you trying to move away from?" 46. "Are we moving fast enough for you?" 47. "What is the most important thing I can tell my CEO about your business?"

For the VP of Sales / CRO: 48. "How will this help you ramp new reps faster?" 49. "Are you missing quota because of [Problem] or because of [Process]?" 50. "How does your current stack impact forecast accuracy?" 51. "What is your strategy for increasing ACV this year?" 52. "If we automate [Task], where will your reps reallocate that time?" 53. "How are you currently coaching against this objection?" 54. "What does your ideal dashboard look like?"

For the CTO / Technical Buyer: 55. "How much technical debt is your team carrying right now?" 56. "What are your requirements for API integration?" 57. "How do you handle data privacy and GDPR compliance?" 58. "What does your deployment timeline realistically look like?" 59. "Who will own the maintenance of this tool internally?" 60. "Do you prefer a cloud-based or on-premise approach (and why)?" 61. "What security certifications are non-negotiable for you?"

For the Marketing Leader: 62. "How is sales currently following up on your leads?" 63. "Are you struggling with attribution for this channel?" 64. "How will this help align Sales and Marketing messaging?" 65. "What content assets are your reps missing during calls?" 66. "How do you measure the quality of an MQL?"

For the Customer Success Manager: 67. "What is the #1 reason customers churn today?" 68. "How smooth is the handoff from Sales to CS right now?" 69. "What does a 'healthy' customer look like in your data?" 70. "How much time do you spend on support tickets vs. strategic advice?" 71. "If we fix [Problem], how does that change your onboarding time?"

Closing / Commitment Questions: 72. "Based on what we've discussed, is there any reason we shouldn't move forward?" 73. "What part of our proposal are you least comfortable with?" 74. "If I send the contract today, what steps happen on your end?" 75. "Do you feel we have understood your business problems correctly?"

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Why memorization fails

You just read 75 questions. In the heat of a live call, you will remember maybe three.

When a prospect throws a curveball objection, your brain enters "fight or flight" mode. You revert to safe, generic scripts. This is why static lists of questions (like this one) are useful for prep, but useless for execution.

To handle objections dynamically, you need prompts that adapt. Read more on objection handling 2.0.

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How Nomi fits

Nomi is not a list of questions on a PDF. It is a Real-Time Sales Copilot. It listens to your conversation, detects the context (e.g., "The prospect is talking about budget"), and surfaces the exact right question on your screen, instantly.

Instead of memorizing 75 questions, your reps just need to read the screen. This ensures:

• Consistency: Every rep asks the right questions.
• Depth: You never forget to quantify the pain.
• Focus: You listen to the client, not your own internal monologue.

Nomi users close about 12% more deals by bridging the gap between knowing what to ask and actually asking it.

Ready to upgrade your discovery? Try Nomi for free.

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References

• Gartner – The B2B Buying Journey 2025
• Industry Benchmarks – 2025 Sales Discovery Data
• Industry Benchmarks – Talk-to-Listen Ratio in Sales Calls
• Bain & Company – AI Transforming Productivity in Sales 2025