The cheat sheet outlines 11 essential questions plus 3 bonus ones to guide effective software sales discovery calls, stressing that asking between 11 and 14 questions is optimal for win rates. The questions help sellers learn about a prospect’s role, team setup, workflow, pain points, IT environment, and current solution costs and adoption. They also probe for desired capabilities, decision-making processes, evaluation criteria, and next steps. Bonus questions address prior buying experience, user feedback, and quantifying problems in business terms. Together, these structured prompts uncover needs, build trust, and drive more focused, value-based sales conversations.

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