The Underrated Skill in Sales and Customer Success: Listening

The Underrated Skill in Sales and Customer Success: Listening

There’s no shortage of content on listening. Books. Courses. Podcasts. Role-play exercises. Anyone in a customer-facing role knows listening is important. And yet, it remains one of the most underdeveloped and overlooked skills in Sales and Customer Success. I’ve seen it play out time and time again.

Honestly...I’ve been guilty of it myself. Years ago, I walked out of what I thought was a flawless enterprise pitch. My deck was tight. I had strong rapport with the stakeholders. I even had executives nodding along. As we closed, I asked, “Do you have any concerns?” The CIO paused, then said, “No, I think we’re good.” Then they went dark. Later I heard through a partner that we’d lost the deal. When I got feedback, here’s what I heard: “You guys didn’t really listen. You had the right product, but it felt like you came in with a solution before we finished explaining the problem.” Wow! That stung. I thought I was listening. I’d taken notes, nodded, even paraphrased a few things. But in reality, I was just waiting for my turn to speak. That moment changed how I approach every conversation.

I’ve noticed four core reasons why listening remains a blind spot for AE's and CSM's:

🎯 Performance Pressure Overrides Presence

Whether you’re chasing quota or a retention target, you’re focused on solving, not absorbing. Your mind is racing ahead: What’s the next step? What’s the close plan? That internal noise drowns out the customer’s voice.

📊 It’s Not on the Dashboard

AE's and CSM's are measured on calls made, emails sent, and deals closed. Sales and CS leaders don’t measure listening, at least I never have in my leadership roles. Because it’s intangible, it often gets ignored. But some of the most powerful insights come from what a customer hints at, not what they say outright.

📢 We’re Trained to Pitch, Not to Pause

Most AE and CSM training focuses on what to say. Very little trains you on how to be quiet and curious. But asking “Can you tell me more?”, and sitting in silence, as uncomfortable as it may feel, is where trust begins.

👍 We Confuse Listening With Agreement

If we are honest, sometimes we avoid truly listening because we don’t want to hear hard truths. I mean, who really wants to hear pricing concerns, onboarding missteps, internal friction? But listening doesn’t mean agreeing. It means acknowledging. When customers feel heard, they soften. When they don’t, they escalate.

If I’ve learned anything in 16+ years of revenue roles, it’s this: Listening isn’t passive. It’s a power move. It builds trust. Reveals real problems. Uncovers urgency. It's not sexy. You won’t see it in your CRM. But it's the skill that separates the average from the exceptional. So, the next time you’re on a call, ask one more follow-up question. Let the silence stretch. Truly hear what your customer is saying. You just might be surprised by what you learn!