

Questions to Ask About Your Deal
Jun 17, 2025
Antonella O’Day, a seasoned sales leader, shares her expertise on deal qualification and risk assessment. She discusses crucial questions sales reps should ask to assess their deals effectively. The conversation highlights understanding customer perspectives to gain a competitive edge, decoding their decision-making process, and overcoming roadblocks with the help of champions within organizations. Additionally, Antonella stresses the importance of identifying sales risks and proactively strategizing to tackle potential obstacles.
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Validate Customer's Business Problem
- Always confirm the business problem directly with the customer and validate it across all stakeholders.
- Understand the alignment with strategic initiatives and consequences if they do nothing or move forward.
Confirm Customer Sees Differentiation
- Ensure the customer clearly understands your solution's differentiation versus competitors and internal options.
- Get the customer to articulate in their own words why your solution is superior to avoid assumptions.
Understand Decision-Making Process
- Know exactly how the customer will make the decision, who is involved, the timing, and the approval process.
- Understand timing from the customer's perspective to avoid delays or surprises in the sales cycle.