The Best Sales Call I Ever Had Took Less than 2 Minutes

Every entrepreneur has to learn to sell, and it’s a lot easier than you think.

Aaron Dinin, PhD
Feb 18 · 5 min read
Image courtesy Andrea Piacquadio via Pexels

When I was a young entrepreneur first learning to build startups, an early mentor gave me a piece of advice about sales that seemed ridiculous at the time. Then I actually tried it and was amazed by how well it worked.

I still remember our conversation. We were sitting in a coffee shop in Philadelphia and I was complaining about a potential customer I’d spent hours trying to close. The prospect backed out of the deal at the last minute because it “wasn’t what they really needed.”

“No matter what I said, I couldn’t convince her to change her mind,” I complained. “I can’t believe she wasted all that time only to decide she didn’t actually need it. Why didn’t she figure that out in the beginning?”

“That’s not her job,” my mentor reminded me. “It’s your job.”

“How am I supposed to figure out what she needs?” I asked, skeptically. “It’s not like I’m inside her head!”

“That’s true,” he said. “You aren’t inside her head. But if you want to be a successful entrepreneur, you have to figure out how to get inside the minds of your potential customers.”

“Yeah?” I responded. “And how am I supposed to do that?”

“Well, you have to become a good salesperson,” he said.

“So you mean I have to get good at talking to people?” I asked. “I already feel comfortable with that. I talked with that person for hours. We had great conversations.”

“Most people think being great at sales means being great at talking to people,” he replied. “But any good salesperson will tell you that’s not actually true. Instead, being great at sales means being great at listening to people. You have to ask questions and listen carefully to the answers.”

I remember, at the time, thinking it was some of the dumbest advice I’d ever been given. How was I supposed to convince people to buy my product by letting them do all the talking? But my mentor insisted I should try it. “On your next sales call,” he implored me, “focus on asking questions. I know it’s going to feel a little strange, but try it and see what happens.”

“OK,” I grumbled. “I’ll give it a shot.”

By coincidence, I had a sales call scheduled later that afternoon. It was with the director of marketing at a 100+ person tech startup, which was a perfect customer for the type of product I was selling.

When we got on the phone, I remembered what I’d promised my mentor. So, rather than jumping straight into my pitch, I asked a simple question: “How’d you discover my company?”

“Well,” he said, “We really need something that can help us better track the emails we’re sending to marketing prospects so we can make sure the right people are receiving the right kinds of messages based on the data we’ve got stored for them in our CRM. I was doing research on tools that could help us do that and came across your company.”

“Really?” I said. He’d just described a completely different service than what my company could provide. “Unfortunately,” I continued, “that’s not really what we do.”

“It isn’t?” he replied. “I thought that’s what I read somewhere.”

“Nope,” I assured him. Then I briefly explained my company’s services.

“Oh,” he said. “Well that sounds interesting, but it’s not something we need right now.”

“No problem,” I assured him. “But I think I know what you’re looking for. We actually use a great company that helps us do what you’ve described,” I explained, and then I gave him the name of the product we’d been using.

“Thanks!” he said, and then we hung up.

Later that evening, I got a text from my mentor.

“Did you try my suggestion?” he asked.

“I did,” I answered. “The call lasted less than 2 minutes and he didn’t even want to hear our pitch because he decided it wasn’t what he was looking for. So not really such a great sales strategy! =)”

“Are you kidding? That’s great!” he texted back.

“It is?” I replied.

“Yes!!!!!!!” he wrote. “In less than 2 minutes you saved yourself hours of work trying to convince him to buy something he didn’t really want or need, which would have most likely resulted in the same outcome. That’s a great sales call!!!!!”

After considering his point for a few moments, I realized that not only was my mentor right, the way I’d been trying to sell my product was completely backwards. I’d spent countless hours trying to convince people they needed my product. However, what I should have been doing was finding people who already wanted what my product could do. When you find people who are already looking for a product like yours, you don’t have to convince anyone of anything. You just show them you have it, and they’ll buy. My mentor’s advice was his way of trying to explain that the best way to find the people who already wanted what I’d built was by asking questions.

When you ask prospective customers questions, they’ll tell you what they’re looking for. Sure, if it turns out they’re not looking for something your company does, you could decide to spend hours trying to convince them to buy something they never intended to buy. But that’s a huge challenge. The better choice is to quickly move on to a new prospect.

That’s not to say it’s impossible to sell someone something they weren’t looking for, but it’s certainly not easy. There’s much less friction when you focus on potential customers already in search of a solution to the problem your startup solves. It’s easier, faster, more efficient, and it’ll likely make your sales process more successful.

It also might have some unexpected positive results. For example, remember the story I told you about the sales call that ended in less than two minutes? A couple months later, the same guy emailed me out of the blue. “That suggestion you gave us was great,” his message said. “Now I think we’re also ready to try what your company does. Can we schedule a demo?”

One 30 minute demo later, I’d closed a $10,000/year contract. And it was all because I learned to listen to what my potential customers wanted instead of trying to tell them what I thought they needed.

The Startup

Get smarter at building your thing. Join The Startup’s +793K followers.

Sign up for Top 10 Stories

By The Startup

Get smarter at building your thing. Subscribe to receive The Startup's top 10 most read stories — delivered straight into your inbox, once a week. Take a look.

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Aaron Dinin, PhD

Written by

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @ aarondinin.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +793K followers.

Aaron Dinin, PhD

Written by

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @ aarondinin.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +793K followers.

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store