Sales has a reputation for being all about the “big pitch” – the dazzling monologue that “wows” the client and wins the business. But here’s the truth: don’t we all like to talk? It feels good, it feels smart, and it feels like progress. Except in sales, that instinct is often the very thing that gets in the way. The real winners aren’t the ones who can talk the longest, they’re the ones who know how to ask better questions and then stop to listen. 

Good questions unlock honest conversations. Ask someone “What’s your biggest challenge this quarter?” and you’ll get surface-level answers. Ask “What’s keeping you up at night?” and suddenly, you’re not a salesperson anymore, you’re a problem solver. The best salespeople aren’t experts in delivering “the pitch;” they’re experts in uncovering “truths” people don’t always say out loud. 

Most prospects can smell a script a mile away. What they don’t expect is someone who remembers that small detail they mentioned last week or picks up on what they didn’t say at all. Listening isn’t passive – it’s active, and it’s a superpower that builds trust faster than a flashy deck ever will. 

Let’s talk about rejection. It stings – no way around it. But in sales, rejection is data, not drama. A “no” tells you what didn’t work or what priorities shifted. Treating rejection as research keeps your ego out of the way and keeps you moving forward with good questions and sharper instincts. 

Your energy, confidence, and curiosity walk into the room before your product does. People buy from people, not logos. If you show up like someone they want in their corner, the sale often takes care of itself. 

These lessons aren’t about gimmicks or quick wins; they’re about building a mindset that keeps you sharp for the long run. When we’ve learned to ask better questions, listen harder, and stay humble, we stop “selling” and start collaborating. And that’s where the real magic (and the real business) happens. 

Ears before ego by Joel Kaplan