AI Discovery Call Checklist: 18 Questions I Would Ask Before a Proposal

AI Discovery Call Checklist: 18 Questions I Would Ask Before a Proposal

ByCodex Admin

By Oliver Bennet

A discovery call should not feel like casual small talk with a quote at the end. It should help both sides decide whether the project makes sense. When the call is structured, the proposal becomes easier to write and much easier for the customer to understand.

If I were building a discovery process for a small service business, I would use AI as the call-prep and call-summary layer. I would not let AI lead the conversation. The owner or salesperson should still listen, notice hesitation, and make judgment calls.

18 questions I would ask

  1. What made you reach out now?
  2. What problem are you trying to solve?
  3. What happens if this does not get fixed?
  4. What have you already tried?
  5. What does a good outcome look like?
  6. Who will use or approve the final result?
  7. What timeline are you working toward?
  8. Is there a deadline behind that timeline?
  9. What budget range are you planning around?
  10. Are you comparing other providers?
  11. What would make this feel like a bad investment?
  12. What information do you need before deciding?
  13. What constraints should we know about?
  14. What tools, systems, or people are involved?
  15. Have you done a project like this before?
  16. What went well or badly last time?
  17. What is the next step after this call?
  18. Who should receive the proposal?

The call structure I prefer

I would split the call into four parts: context, diagnosis, fit, and next step. That keeps the conversation from wandering. It also prevents the common mistake of pitching too early before the customer has explained the real issue.

  • Context: why they reached out and what changed.
  • Diagnosis: what is causing the problem.
  • Fit: whether your service is the right match.
  • Next step: proposal, paid audit, referral, or no-fit response.

AI call-prep prompt

Act as a discovery call assistant.
Business: [business type]
Lead intake answers: [answers]
Create a call prep brief with:
1. likely customer goal
2. possible risks
3. questions to prioritize
4. what not to promise yet
5. recommended next step if the lead is a fit

AI call-summary prompt

Turn these discovery call notes into a proposal brief.
Include: client problem, desired outcome, scope clues, constraints, decision makers, budget signal, timeline, objections, and next action.
Notes: [notes]

My recommendation

Do not ask every question mechanically. Use the checklist as a safety net. The best discovery calls feel conversational, but underneath that conversation there is a clear structure. AI is useful because it helps you keep the structure after the call, when details are easy to forget.

FAQ

Should I send questions before the call? I would send a short intake form before the call and keep deeper questions for the conversation. This saves time without making the customer feel interrogated.

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