Why Deals Stall: 5 Questions to Ask Before You Forecast
- Wayne Johnson
- Jul 7
- 3 min read
Updated: Jul 8
“It looks like everything’s on track—but then, crickets. What happened?”
Raise your hand if you’ve ever been there. One minute your deal is cruising, and the next? It’s quieter than a Sunday morning. You feel it: the dreaded stall. No updates. No movement.
If you're nodding along—you're not alone. Here’s the thing: most forecast misses aren’t surprises. They’re the result of undetected stalls during discovery. You just didn’t ask the right questions, at the right time, to uncover potential speed bumps.
Let’s fix that. Here are 5 game-changing questions to elevate every discovery and catch issues before they threaten your forecast.
1. “What would stop this deal from closing?”
This isn’t contrarian for the sake of it. It’s practical. Reps ask “what will make this work,” but often skip “what could make it break.”
Why: You can only prepare for risks you’ve uncovered.
How: Phrase it neutrally:
“What conditions or signals would need to change before we moved forward?”
What to listen for:
Budget blocks
Leadership changes
Vendor integration concerns
Or even vague hesitations like, “I need to think about it.”
Anything can stall a deal if not surfaced early.
2. “When is the final decision by—and who signs off?”
A timeline without clarity is like driving with a faulty GPS.
Goal: Pin down both when and who.
Follow-up:
“What milestones or meeting outcomes would get us to that decision?”
👉 If no one knows exactly when or who—you just uncovered a stall waiting to happen.
3. “How will you evaluate us compared to others?”
Early-stage deals often skip the comparator conversation—and that’s a costly mistake.
Why: You want to know whether you're competing on features, price, integration, support, or ROI.
Pro tip: Ask for other contenders by name.
“Are you considering [┅] or [┅]? What matters most when you’re comparing?”
This lets you tailor your messaging and stand out well before proposals hit the table.
4. “What needs to be true internally for this to be a win?”
This is where you shift from a “sale” to a “partnership mindset.”
Goal: Identify internal expectations and success factors inside the prospect’s org.
Examples to uncover:
“You need 10% ROI by Q4.”
“IT must integrate with X system by go-live.”
“Sales must roll it out in all regions.”
Why it matters: If you can’t meet those internal success criteria, you’re not solving the real problem—and that’s where stalls come from.
5. “If nothing changes from today to next week—will this close?”
This is your check-in for current momentum:
Sometimes just asking gets things moving again. Maybe a key internal approver is traveling, or someone’s sick. Either way, you’re back in the driver’s seat.
Why These Questions Matter
Benefit | Outcome |
Forecast Accuracy | You don’t guess—you know where deals stand. |
Risk Reduction | You identify and address stalls before they become problems. |
Stronger Relationships | You demonstrate credibility—and care—for the buyer’s world. |
Strategic Pitches | You can align to their core criteria—and spotlight what matters most. |
Quick Recap: Field-Tested Question Script
“What could stop this from progressing?”
“Who’s the final decision-maker, and when do they decide?”
“Are you evaluating anyone else? What’s the most important differentiator?”
“What internal success factors must be met?”
“If today was next Friday, would this deal cross the finish line?”
Final Word
Deals don’t stall in one dramatic event. They stall in small silences, missed milestones, and unasked questions. Those five questions aren't just for prep—they’re your proactive stall detector.
So next forecast cycle, bring them up before your deal goes “radio silent.” Chances are, you’ll spot and dodge stalls before they happen—and significantly improve your win rate and forecast accuracy.
Stay curious—and keep your deals moving.