Most founders open discovery with the same question.
"What's keeping you up at night?"
It's a dead question. Nobody answers it honestly. The prospect either lies, gives a non-answer, or repeats whatever they read in last week's industry newsletter. You learn nothing. You spend the next 20 minutes building a pitch on a fake foundation.
The reason it fails is structural. The question asks the prospect to volunteer the most vulnerable thing about their business to a stranger they met 90 seconds ago. The honest answer is "you, right now, with this call." They don't say that. They say "alignment between sales and marketing." You nod. The deal dies in stage three.
Keenan's Gap Selling has a better model. Every deal is a gap between where the prospect is now and where they want to be. Your job in discovery is to map the gap, then quantify what it costs them to leave it open. Three questions do that work.
One. The current-state question.
"Walk me through how you handle [the specific process] today. Step by step, who does what."
This question is impossible to answer with a buzzword. They have to describe a real workflow. You hear the gaps in their own words. The handoff that drops leads. The spreadsheet someone forgot to update. The Slack channel where leads die. You don't have to dig for the problem. They narrate it for you.
Two. The future-state question.
"If you could wave a wand and have this work exactly the way you want, what does that look like in six months?"
This is the Hormozi dream-outcome question, scoped to a timeline so they have to be specific. "Better pipeline" is not an answer. "Three qualified meetings a week, every week, by Q4" is an answer. Now you have a measurable gap.
Three. The cost-of-the-gap question.
"What does it cost you right now that this isn't working?"
Watch them do the math out loud. If they can't, the deal isn't real. If they can, they just sold themselves on the size of the problem before you sold them on the solution. Hormozi calls this the cost of inaction. Keenan calls it the cost of the gap. Same idea. It's the question that turns "interesting" into "we need to fix this now."
Three questions. Current state. Future state. Cost of the gap.
If your reps are using "what's keeping you up at night?", they're guessing. If they're using these three, they're diagnosing.
Steal the questions. Run them on Wednesday's call. Report back.
One piece worth your time this week
A first-time AE posted in r/b2b_sales this week titled "Closed my first b2b deal last month after 6 months of trying, here's what actually got it done." 39 upvotes. Worth the four-minute read. Read the thread here.
His list of what changed once the deals started landing: stop trying to convince people they have the problem, discovery matters more than the demo, multithread or die, don't drop pricing on the first call, build urgency from the prospect's own words, expect to close on follow-up four to seven.
The comments section is doing its job. One commenter posted, "Did you not get any training? Everything you are saying is common knowledge in sales."
She's right. And that's the point.
Everything in his post is common knowledge. Almost none of it is common practice. Most reps know they should multithread. Most reps know the demo is not where the deal is won. Most reps know the deal isn't dead on follow-up four. The gap isn't knowledge. The gap is that nobody runs the boring playbook every day with the discipline it takes for those fundamentals to show up in the pipeline.
The OP didn't reinvent sales. He stopped skipping the parts everyone agrees matter. That's usually the whole job.
Talk soon,
Justin