Mike, a high-energy salesperson on a Connecticut sales team, prided himself on having a long list of “active” prospects. Every Monday, during pipeline meetings, he made sure everyone knew it.
But when his manager, Jacqueline, took a closer look, she discovered a problem. Many of Mike’s “active” prospects weren’t really moving. Some had been in his pipeline for months—twice as long as other team members’ deals.
The issue wasn’t a lack of effort. Mike was simply holding on to opportunities that were never going to close.
Two Critical Questions Sales Leaders Should Ask
Having a big pipeline feels good. It looks productive and gives the illusion of momentum. But a long list of deals doesn’t always mean success.
The best Connecticut sales professionals regularly ask two key questions about their pipeline:
How many of these opportunities are likely to close?
How long will they take to close?
Mike wasn’t asking those questions—but Jacqueline was. What she found was eye-opening:
It took Mike 60 days to close winning deals, but 150 days to finally walk away from losing ones.
He invested huge amounts of time creating proposals, sending follow-ups, updating CRM records, and discussing these dead-end deals in team meetings.
When you add in the time of technical and finance teams supporting those proposals, the cost of holding on became painfully clear.
Why Salespeople Hang On Too Long
Why do so many reps hold on to stalled deals?
Culture: In many organizations, a “full” pipeline is mistaken for success.
Fear: Some sellers fear scarcity—if they let go of an opportunity, they might not find another.
Ego: Admitting a deal is lost can feel like admitting failure.
This “scarcity mindset” leads to wasted time, lower productivity, and longer sales cycles.
The Power of the “Sell-By” Date
Jacqueline decided to make a change. She introduced a simple but powerful concept:
Every opportunity gets a “sell-by” date.
If the deal wasn’t closed by that date, the salesperson had to prove why it still belonged in the pipeline—or remove it entirely.
The result?
✅ Mike stopped managing stale deals and started pursuing new, qualified opportunities.
✅ The team’s average sales cycle shortened.
✅ Win rates improved.
By applying this discipline, Jacqueline’s Connecticut sales team became more focused, efficient, and profitable.
Takeaway for Connecticut Sales Leaders
A crowded pipeline isn’t the goal—a healthy, moving pipeline is.
Regularly review your sales pipeline and apply expiration dates to deals that linger. It’s not about losing opportunities; it’s about freeing up time for the ones that matter most.
When you set a “sell-by” date, you give your team permission to focus on progress—not paperwork.
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