The art of sales lies in the ability to ask the right questions at the right time. This document compiles some of the most effective questions and strategies shared by real sales experts shared on Reddit.

These questions have been categorized to align with the different phases of a sales conversation, from the initial discovery call to closing it. Whether you're a seasoned sales professional or just starting, these questions will help you gain a deeper understanding of your prospect's needs, identify pain points, and position your solution effectively.

Phase 1: Opening and discovery questions

These questions are designed to understand the prospect's current situation, pain points, and the urgency of solving their problem.

• "What’s going on in your world that made you decide to talk to me?"
• "Why did you agree to meet with me today?"
• "What’s the biggest headache in your workflow right now that you’d love to get rid of?"
• "Why hasn’t this problem been fixed before today?"
• "What do you like about your current set-up or situation?"
• "What are you currently doing/using?"
• "Why do you feel now is the right time to move forward?"
• "What’s leading the conversation, schedule, scope, or budget?" (sometimes up-front)

⇒ Lear their situation without introducing your solution.

Phase 2: Uncovering pain and consequences

Once the prospect's situation is clear, the next step is to explore the depth of the problem, the impacts of inaction, and the pain points they’re experiencing.

• "What happens if nothing changes?"
• "If you didn’t solve this problem in the next 6–12 months, what would the impact be?"