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Your pipeline is misleading you.
We see it every year. Deals sitting at 50% for 60+ days. Close dates pushed from October to November to "end of year." Reps refreshing their inbox instead of working the deal. Forecast calls that feel like guesswork.
Here's what actually moves deals in the final weeks.
Stuck Deals Start With Bad Discovery
When reps rush the first call, they get the "what" but miss the "why” and “how”. That missing context kills urgency later.
Coach your team to go deeper: What do they want? Why do they want it? How are they going to get to the results they are striving for? What changes if nothing really changes? If your reps can't answer all three, the deal isn't qualified. It's just sitting there.
Artificial Deadlines are so 2010
"Sign by the end of quarter or end of month, get 10% off" means nothing to a buyer with their own priorities.
What works:
- Time to value: illustrate the positive business outcomes and have all stakeholders repeat them back to you.
- Work backwards from their go-live date: if implementation takes six months and they need it in April, they're already behind. Use that.
- Pressure-test close dates: when a rep says "Thanksgiving," ask, "Who on the buyer's side agreed to that?" No answer = not a real date.
- Tie incentives to something real: "December crushes our legal team. Sign early, we pass the savings back." Logic expires. Arbitrary dates don't.
Match Tempo, Don't Force It
Your reps have urgency. Buyers have their own pace. The job is matching it, not overriding it.
Forced urgency creates friction. The wrong kind. When a rep doesn't have enough pipeline, they push too hard on the deals they do have. Buyers smell desperation.
Fix: Hold reps to three self-sourced meetings per week. More pipeline means less pressure on any single deal.
The Three Whys and a Who
I've tried every methodology. These days I keep it simple:
- Why do they want to do anything? Every rep gets this far.
- Why do they want us? This is where most reps stop digging.
- Why do this now? This is what separates pipeline from closed-won.
- Who cares about this and will see it from evaluation to go live?
When you have those answers, don’t stop validating the answers, keep asking on every call. Repetition of message matters. You're not manufacturing urgency. You're playing back what they already told you.
Signals That Move Deals
Get on text. Flip the ask: "Here's my number if you ever need anything." Now you have a faster channel and a reason to stay in touch.
Executive matching. Have your CRO/Executive send a two-line note to their executive stakeholder. "Excited to partner. Here if you need anything escalated." Execs should also connect on LinkedIn.
The PS trick. End emails with an unrelated question. "PS - Know anyone at [company]? Happy to intro." Forces a reply. Gets the rest of the email read.
Buyers Need Comfort
You can't force a close. But you can arm your champion.
Know how they're measured. A VP of Demand Gen doesn't care about content views. They care about MQLs and pipeline. Speak to that.
Paint the outcome. "Here's what Q1 looks like with us. Here's Q2." Make it concrete.
Ask the hard question: "If not us, what's the plan to hit those numbers next year?" That's not pressure. That's partnership.
The Bottom Line
Precision beats pressure. A tremendous leader I worked for used to always say “The deal is not real until there is some tension.” If you shy away from confrontation or uncomfortable questions you are setting yourself up for disappointment.
Know your buyer. Know their timeline. Know what they want and why they want it. Build enough pipeline that you don't have to force anything.
Real urgency comes from understanding what's at stake. If you do that right, you're not creating urgency. You're just pointing out what's already true.
Request a demo to see how People.ai gives you visibility into what's actually happening in your deals.