Don't Swing at The First Pitch
Surface-level pain feels like the pitch to hit. But reps who wait, listen, and dig deeper close bigger. Active listening isn’t about being polite - it’s about uncovering impact, urgency, and truth.
Active listening turns surface-level pain into urgency, impact, and closed revenue.
A couple companies ago, I was ramping into a new leadership role - getting up to speed on the team, the pipeline, and our customer base. Like any new sales leader would, I jumped into Gong to start reviewing customer calls and deal cycles.
What I found was both disheartening, and yet encouraging. We could fix this.
The conversations were solid. Pain points were clear. Prospects weren’t holding back. But we were missing out.
Again and again, I noticed our reps were stopping at the first sign of pain - so fixated on trying to hit what looked like a softball tossed right over the plate - and completely missed.
Swing. Miss.
Or best case, we jumped at the first fastball and missed the hanging curveball that would’ve cleared the bases. We settled for singles when homers were on the table.
It wasn’t just a lack of questions. It was a lack of active listening. We weren’t really hearing what our buyers were saying.
We weren’t validating their reality or exploring what the pain actually meant for their business.
And that gap - the space between hearing and understanding - is where deals are won or lost.
In sales, it's easy to jump to solving the problem. But the reps who win the most? They're the ones who slow down, ask the right questions, and truly listen. Active listening is a competitive advantage backed by data.
Here’s why it matters:
Gong.io found that top-performing reps speak only 43% of the time on sales calls - letting the buyer talk 57%.
Full article HERESalespeople who use active listening techniques see up to a 30% boost in performance.
Full article HERE69% of buyers say they expect sales reps to listen more than they talk.
Full article HEREListening closely helps uncover the true business impact of the problem - not just the surface-level pain.
It builds trust and rapport, leading to larger deals, shorter cycles, and more referrals.
Tips for practicing active listening:
Ask open-ended questions that uncover context, IMPACT, not just symptoms.
Repeat back key points to confirm understanding (this also gives you time to think about a deeper next-level question)
Avoid cutting in. Let the customer fully process and express.
Pay attention to tone, hesitation, and body language - what’s unsaid is often the gold.
Bottom line: Listening is selling.
And in a noisy, solution-happy world, the reps who truly hear their buyers are the ones who win.
Thanks for reading!
— Grant 👋
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Compiled and aggregated from a network of sales leaders in SaaS, Stretch VP showcases learnings, insights, and experiences as well as best practices to overcome common hurdles, obstacles, and setbacks in your quest for excellence as a sales leader in SaaS.
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