The best reps in Q4 aren’t just great at selling; they’re also effective at managing their time. They’re great at understanding what’s already happening inside their buyer’s business and then attaching to it.
It’s only possible if you know how to uncover the “why now?”
Not the corporate vision. Not the generic priority. The actual reason someone inside the company needs this to happen within a specific window, or why they’ll quietly kill the project if it doesn’t.
Most reps never find it. They default to “next steps” and MEDDICC fields, but they never push far enough to uncover what’s motivating urgency.
What we see over and over again is this: the best ones treat timeline questions as a diagnostic tool, not a formality.
Most Reps Ask “When?” Great Reps Ask “Why Then?”
Good:
🗣️ “When are you hoping to get this implemented?”
😴 Answer: “Ideally Q1, but we’re still evaluating.” (Which is buyer-speak for we’re not really committed.)
Better:
🗣️ “If you’re targeting Q1, what happens if it slips to Q2?”
🧠 Now you’re testing for consequences.
Best:
🗣️ “What’s going on in the business that makes this a now-problem instead of something that could wait 6-12 months?”
🧨 Now you’re probing for the compelling event behind the stated timeline.
If the buyer can’t answer that or gives a vague response, you don’t have urgency. You have interest, and interest doesn’t close.
Every Deal Has a Clock. You Just Have to Find It.
Every buyer operates under constraints. Sometimes it’s a budget cycle. Sometimes it’s a regulatory deadline. Sometimes it’s internal political momentum that will dry up if not captured now.
If you don’t find that… the thing that creates personal and professional risk for the buyer, you’re stuck selling features into the void.
Managers Are the Urgency Multiplier
At CoachEm, we teach managers to coach reps to get sharper at this. We give them a lens to inspect how often reps are:
- Asking surface-level questions vs. timeline consequence questions
- Documenting real compelling events vs. wishful thinking
- Revisiting urgency in every stage, not just discovery
And we make that a weekly coaching conversation, not something left to chance. Our platform shows you whether that’s happening. If not, we guide the manager on what to coach this week, not in QBRs three months too late.
The Powerful Question That Forces the Truth
Here’s a favorite from my playbook that I love coaching into reps:
“What happens if you do nothing?”
It’s simple, but it’s uncomfortable for buyers, and that’s the point. If the answer is “nothing really,” then you’re not solving a mission-critical problem. You’re an RFP participant.
Coach that question into every deal review. Then coach your managers to ask:
“Did we uncover what happens if the buyer doesn’t move forward?”
If not, push the rep to go back. And equip them with the language to do it well.
Don’t Just Chase Deals. Coach the Clock.
Deals don’t stall because people don’t like your product. They stall because no one’s hurting badly enough to act. If you don’t uncover the pain or the deadline, it’ll slip. Guaranteed.
The best reps coach their buyers through their own timeline logic. The best managers coach their reps to ask better questions. And the best leaders don’t settle for a pipeline that’s full but fragile.
Coach the clock. Start with: “What’s the real reason this has to happen now?” And don’t let go until you get a real answer.
If you want to give your managers a system that helps them uncover urgency, coach deal velocity, and spot weak pipelines before they stall, we should talk.
