Most founders I watch run discovery calls on instinct. They’ve done hundreds of them. The instinct is often good — but it’s not transferable, it doesn’t train the first AE, and it doesn’t survive the week you’re sick and the call falls to someone else.
Here is the six-question structure I’ve used and refined across a dozen founder-led sales orgs. It fits on an index card. It works on every call.
Why six? Why not twenty?
Long scripts get abandoned. Founders skip questions. The call becomes an interrogation. Six questions is the maximum a natural conversation can absorb before the prospect notices you’re reading from something.
The goal is not to fill a form. The goal is to understand three things with enough clarity that you can either disqualify the deal or walk out knowing the next move.
The six questions {#the-six-questions}
1. “What triggered the call today?”
Not “how did you hear about us.” What changed. Urgency lives in the trigger. A funding round, a new board member, a painful quarter, a competitive loss — these are events that create a genuine buying window. If there’s no trigger, the timeline is probably “whenever.”
2. “What does the problem cost you right now?”
Not “what are your pain points.” What does it cost. Founders are often great at describing the problem but fuzzy on the number. Push. “If the sales cycle stayed at 90 days instead of shrinking to 60, what does that mean for ARR this year?” Costs that can’t be quantified rarely generate budget.
3. “Who else cares about this?”
You need to know the buying committee before you’ve written the proposal. This question surfaces it naturally. The answer tells you who to involve in later calls, who the champion is, who the economic buyer is, and whether there’s a technical veto lurking somewhere.
4. “What have you tried?”
This is the diagnostic question. Every failed previous attempt tells you something: what the org actually has bandwidth for, where the resistance lives, what “good” looks like in their mental model. It also tells you whether they’re ready — if they’ve tried nothing and you’re the first call, the timeline is probably longer than they think.
5. “What does success look like in 90 days?”
Forces specificity. “Better sales” is not a success metric. “Founder off all discovery calls by October” is. “SQL definition agreed and in CRM” is. If they can’t give you a concrete answer, the engagement will drift — and that’s a problem for both of you.
6. “What would make this the wrong decision?”
The best question, asked last. It de-escalates the pitch dynamic, surfaces objections before they become deal-killers, and shows you’re not trying to sell something that won’t fit. Founders who ask this question close at higher rates. Counterintuitive but consistent.
The card
Print this. Have it in front of you for the first ten calls. Then you won’t need it.
1. What triggered the call?
2. What does this cost?
3. Who else cares?
4. What have you tried?
5. What does success look like in 90 days?
6. What would make this the wrong decision?What to do after
These six questions are the foundation of the CEO Sales Sprint. The sprint takes the way you currently sell — including whatever variations you’ve developed through instinct — and turns it into a playbook that a first AE can execute without you in the room.
If you’re still the only person who can run discovery, it’s time to write it down.