Discovery Questions

Parent: Sam's Call Scripts

Once a prospect is engaged, these are the questions that move them from interest to specifics.

Workflow questions

• "Walk me through what happens when [specific event] happens — start to finish, every step."
• "How many people touch that workflow before it's done?"
• "How often does this happen — daily? weekly? monthly?"
• "What systems are involved? Email, Excel, Sage, Procore — which ones?"

Pain questions

• "What's the most frustrating part of that for whoever is doing it?"
• "When something goes wrong in that process, what happens? How do you catch it?"
• "How much time per week do you think your team spends on this?"
• "Has anyone quit or wanted to quit over this kind of work?"

Cost questions (after pain is established)

• "If you had to put a loaded hourly rate on the person doing it — including benefits, overhead — what would it be?"
• "If we recovered 20 hours a week of that, what would they do with the time?"

Decision questions

• "Who else would need to weigh in on a project like this?"
• "If we showed you something that worked on your real data in 45 days, would there be any reason you couldn't move forward?"

What NOT to ask

• "What's your budget?" — they'll lowball or won't answer
• "When are you looking to start?" — they'll say "still exploring"
• "What other vendors are you talking to?" — feels like sales-y comp shopping

Instead, anchor on the workflow + the pain + the cost. Budget and timing fall into place naturally.

Last updated: 2026-05-24