A VP of Sales has heard every discovery script ever written, usually from the reps trying to sell to them, so the generic ones die on contact. Open with 'what are your goals this year' and you can watch them file you under vendor in real time. The person who owns the number wants you specific, fast, about the gap between the plan and the pipeline, because that gap is the only thing on their mind this quarter. The list below is where that starts; the Claude prompt under it is how you make the questions about their business instead of everyone's.
What a VP of Sales actually cares about
Three numbers run a VP of Sales's week: quota attainment, pipeline coverage, and how fast a new rep ramps. They buy to protect the forecast, so 'innovative' is a yellow flag and 'this closes the coverage gap by next quarter' is a green one. Prep your discovery around the risk to the number and every answer maps cleanly to a MEDDICC field you can drop straight into your deal review. Prep it around your product and you get a polite nod and no second call.
Discovery call questions for a VP of Sales
Copy the list and cut it to the six or eight that fit the deal. Lead with the gap-to-number question; everything else earns its place only if the answer to that one opens a door. Each question is tagged with the MEDDICC field it fills, so your notes drop into the CRM instead of needing a translation pass after the call.
- How is the team tracking to the number this quarter, and where is the gap coming from? (Metrics)
- How many reps are at quota right now, and how long is ramp for a new hire? (Metrics)
- Walk me through how a rep moves a deal from first call to closed today. (Decision Process)
- What is your pipeline coverage ratio, and where do you need it to be? (Metrics)
- When the forecast slips, what is usually the reason, one you can name? (Implicate Pain)
- What would have to change for next quarter to not feel like this one? (Implicate Pain)
- Which part of the funnel keeps you up at night: top of funnel, conversion, or slippage? (Implicate Pain)
- What have you already tried to fix it, and why did it not stick? (Competition)
- If nothing changes, what does that cost you by end of year? (Implicate Pain)
- If you found something that moved the number, what does it take to bring it in? (Decision Process)
- Who else weighs in, RevOps, finance, the CRO, and what do they need to see? (Economic Buyer)
- What has derailed a rollout to your team before? (Paper Process)
- Ninety days in, what number tells you this worked? (Metrics)
- Which rep would you want to pilot this, and why them? (Champion)
Do not read all sixteen out loud; that turns a call into a deposition. Pick six, open with the gap question, and let the answers pull the rest out of you. When you want this tailored to a real account instead of a role, the prompt below does it in one paste.
Generate these for your exact account
The list is the floor: the same questions for every VP of Sales on earth. The call is won by making them specific to the company in front of you, and that is the tedious ten minutes you keep skipping at 8:55 for a 9:00 call. Hand it to Claude. Paste the questions with the prompt below, or point the discovery skill at their URL and let it read the company first.
You are prepping me for a discovery call with a VP of Sales at {{company}} ({{company URL}}).
First, read their website: what they sell, who they sell to, how they go to market, and any signals about the state of their sales team (open roles, recent funding, new segments).
Then take the discovery questions below and, for each one, swap the generic blank for something specific to {{company}}. Keep every question mapped to its {{MEDDICC}} field. Cut the list to the 8 that best fit this deal, sequence them broad to specific, and flag the ONE question most likely to surface a real gap I can act on.
Use only what you can actually read or reasonably infer, and mark anything inferred so I do not assert it as fact on the call.
QUESTIONS:
{{paste the list above}}Generate this for any account
- Discovery call prep skill →The Claude skill that tailors this whole list to a specific account and your framework (MEDDICC, BANT, SPICED).
- Sales discovery questions prompt →The copy-paste prompt version, tailored to the deal in front of you.
Frequently asked questions
What should you ask a VP of Sales on a discovery call?
Lead with the gap between their plan and their pipeline: how they are tracking to the number, and where the shortfall is coming from. A VP of Sales is judged on quota attainment, pipeline coverage, and rep ramp, so specific questions about the number land, while 'what are your goals' earns you a filler answer and a short call. Keep it to six or eight, and map each answer to a qualification field as you go, so the CRM update is a copy job instead of a memory test.
How many discovery questions should you ask?
Six to eight in a first call. More than that and you are interrogating, not listening, and the VP checks out. Pick the ones that surface the gap and the decision process, then let the conversation pull the rest. You are trying to leave with a real next step and enough to fill your framework, not to get through a script.