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DISCOVERY QUESTION PACK

Thirty Gap-Selling questions sorted by call stage. Current, future, gap, impact, decision. Steal what works.

30 questions5 stages9-page PDF

Thirty discovery questions sorted by stage. Built on Keenan's Gap Selling. Map the current state, paint the future state, name the gap, prove the cost of inaction, close the call.

1

Ratio: 70 / 30

The buyer talks for 70 percent of discovery. If you are talking more than 30, you are pitching, not discovering.

2

Numbers force focus

Every question with a number anchors the next claim you make. Get the data out loud.

3

Silence sells

After every hard question, count to three before you say anything. The buyer fills it.

Stage

CURRENT STATE

1
QUESTION

Walk me through what your outbound motion looks like today. Channels, headcount, tools.

Why it works: Maps the as-is so you can name a specific gap, not a generic one.
2
QUESTION

What's the per-meeting cost you're running right now?

Why it works: Forces a number. Numbers anchor every later ROI claim.
3
QUESTION

Of every 100 dials, how many connects, how many meetings booked?

Why it works: Surfaces conversion drop-offs. Keenan: you can't fix a gap you haven't measured.
4
QUESTION

What's your ramp time on a new SDR right now?

Why it works: If it's 60+ days, the floor model has an obvious play.
5
QUESTION

How are you splitting time between prospecting and admin?

Why it works: Productivity gap. Most reps are <2 hours/day in actual conversations.
6
QUESTION

What tools is your team using and which are pulling weight?

Why it works: Tells you the stack, the gaps, and what you'd need to integrate.
Stage

FUTURE STATE

7
QUESTION

If outbound was running where you want it to in 90 days, what would the numbers look like?

Why it works: Gets them to commit a future-state metric out loud.
8
QUESTION

What's the dream version of meeting quality this team is producing?

Why it works: Quality matters more than volume. This question separates serious buyers from price shoppers.
9
QUESTION

Walk me through a perfect Monday at quarter end. What does the team's pipeline look like?

Why it works: Concrete picture beats abstract goal.
10
QUESTION

If you had no constraints, who would your ideal outbound team look like? Mix of senior, junior, geo, channel?

Why it works: Surfaces the buying criteria they haven't articulated.
11
QUESTION

What does the board / CEO need to see from outbound by end of quarter?

Why it works: Identifies the political pressure point. Often the real reason they're talking.
12
QUESTION

What would you stop doing if you knew it wasn't moving the needle?

Why it works: Hormozi: the easiest sale is removing a cost they already regret.
Stage

THE GAP

13
QUESTION

Where's the biggest gap between what you described as today and what you described as the goal?

Why it works: Lets them name the gap so you don't have to.
14
QUESTION

What have you already tried to close that gap?

Why it works: Saves you from pitching what failed. Also reveals their decision-making style.
15
QUESTION

Why didn't that work?

Why it works: The honest answer is where the real problem lives.
16
QUESTION

Walk me through a recent rep ramp that took longer than you wanted. What broke?

Why it works: Stories surface root causes that generic questions miss.
17
QUESTION

When did you first notice this becoming a problem?

Why it works: Anchors urgency. If it's been 18 months, urgency is low; the buyer is comfortable in the pain.
18
QUESTION

What happens if you don't solve this in the next two quarters?

Why it works: Forces the cost of inaction. Without this, every ROI pitch is hand-waving.
Stage

IMPACT

19
QUESTION

If we cut your per-meeting cost by 40 percent, what does that unlock for the rest of the budget?

Why it works: Specific to your offer. Forces them to picture the downstream win.
20
QUESTION

What does missing the pipeline target cost the company in real dollars?

Why it works: Most buyers haven't done this math. Doing it with them creates urgency.
21
QUESTION

Who else feels this gap besides you?

Why it works: Maps the buying committee without sounding like you're mapping it.
22
QUESTION

Whose neck is on the line if this doesn't get fixed by year-end?

Why it works: Identifies the real economic buyer. Often not the person on the call.
23
QUESTION

What's the personal cost to you if this stays broken?

Why it works: Career stake, time, weekends. The personal stake closes deals, not company ROI.
24
QUESTION

Has this kept anyone up at night this quarter?

Why it works: Soft version of the personal-stakes question. Use when the buyer isn't being candid yet.
Stage

DECISION

25
QUESTION

If we figured out a fit, who else needs to be in the room?

Why it works: Multi-thread early or the deal dies later.
26
QUESTION

Walk me through how a buying decision like this normally gets made here.

Why it works: Process discovery. Skipping this is why deals slip a quarter.
27
QUESTION

What's the timeline pressure on getting this solved?

Why it works: Real timeline, not the polite one. Look for the trigger event behind it.
28
QUESTION

If we had this conversation 3 months ago, would it have been a different call?

Why it works: Tests urgency. Buyers who 'should have done this 6 months ago' close. Buyers who 'might think about it next year' don't.
29
QUESTION

What would have to be true for this to be a no?

Why it works: Surfaces objections before they show up at proposal time.
30
QUESTION

If everything we just talked about works, what does the next 30 days look like for us?

Why it works: Closes the call by mutually committing to next steps without it sounding like a close.

KEEP GOING

10 TEMPLATES

Cold Email Templates

10 B2B subject lines and bodies that book meetings, with the rationale and when to use each.

8 OBJECTIONS

Objection Handling Cheat Sheet

Word-for-word LDA responses to the 8 objections you hear every week. Print it and keep it next to the phone.

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