Trust Your Ears, Not Just Your Prep
How Being Over-Prepared Can Backfire
In sales, we often talk about the importance of preparation. Know your prospect. Know their objections. Be ready with the perfect response. But what if I told you that being over-prepared could actually hurt your chances of closing the deal?
I learned this the hard way early in my career. I was one month out of the ramp, and I was about to take my first call alone—no senior, no manager, just me. I had done all the research. I knew the prospect’s title, his responsibilities, what objections he might bring up, and how I’d respond. I was ready.But as the call progressed, something felt off. The prospect kept bringing up use cases that didn’t align with his title, and I was so stuck in my preparation that I didn’t stop to really listen. I was just going through the motions, asking the questions I thought I should ask, waiting for my chance to pitch the solution I had prepared.
The call ended, and I could sense it—there wasn’t going to be a second one.
Later, I reviewed the call, and it became clear what had gone wrong. The prospect had been trying to tell me something important—that he was responsible for a function outside of his typical role because of a bandwidth issue at his company. But I had missed it. I was too focused on the script I’d prepared to hear what was really happening.
I called him back and asked him directly if he was overseeing the other function, and he confirmed it. But by that point, it was too late. I had lost the trust and the chance to continue the conversation.
Why Over-Preparation Hurts Your Listening Skills
We think that being prepared is the key to success in sales, and to some extent, it is. But there’s a fine line between being prepared and being so locked into your plan that you miss what’s really going on.
When you go into a call with assumptions about what your prospect will say, you’re not really listening. You’re waiting for your chance to jump in, to respond with your perfectly rehearsed answers. But sales isn’t about having all the answers—it’s about understanding the problem.
And you can’t understand the problem if you’re not truly listening.
Listening Is More Than Hearing Words
Listening in sales is about more than just hearing what your prospect says. It’s about reading between the lines, picking up on subtle cues, and noticing when things don’t quite match up.
In my case, the prospect’s title didn’t align with the use cases he was bringing up. That should have been my first clue that something was off. But because I was so stuck in my preparation, I didn’t catch it. I was too focused on pushing my agenda to pay attention to what the prospect was really saying.
Why Flexibility Is Key
When you’re over-prepared, you leave no room for flexibility. You go into the call with a rigid plan, and if something doesn’t fit that plan, you try to force it into place. But real sales conversations are fluid. They require you to be flexible, to adapt to what’s happening in the moment.
And that starts with listening.
When you listen, you give your prospect the space to open up. You allow them to tell you what’s really going on, and you can adjust your approach accordingly. That’s how you build trust. And trust is the only way you get a buyer to make a change.
The Lesson: Stop Assuming, Start Listening
One of the biggest lessons I learned from that call was this: Stop assuming. As the saying goes, 'When you assume, you make an ASS out of U and ME.'
Sales isn’t about having all the answers. It’s about asking the right questions and then listening—really listening—to the answers. When you do that, you stop being a salesperson and start being an advisor. You give your prospect the chance to share their challenges, and you position yourself as someone who understands, rather than someone who’s just there to sell.
So next time you go into a sales conversation, be prepared—but don’t let your preparation get in the way of your listening. Because when you truly listen, you’ll not only close more deals—you’ll build relationships that last."
