by Josh Chernikoff
Selling to schools has transformed completely in the last few years. Not long ago, you could casually drop by a school, grab a coffee with a principal, or meet up after hours. These unplanned interactions allowed for a natural way to get to know people and build relationships. A longer in-person meeting wasn’t just about pitching a product—it was about really connecting with the person on the other side, understanding their unique challenges, and figuring out where you could add value.
Now, with most meetings happening online, it’s a different landscape. Virtual meetings are efficient, structured, and often limited to 15 or 30 minutes, making it tough to build the same level of rapport through a screen. The challenge today is making every moment count. For education entrepreneurs, that means shifting away from leading with a product pitch and instead focusing on active listening from the start. By diving right into understanding the specific needs and struggles schools are facing, you can create meaningful connections, build trust quickly, and make your offer stand out—even in a short virtual meeting.
Why Leading with Demos Can Hurt Your Chances
A lot of education companies fall into the trap of relying too much on demos. Many founders or administrators don’t come from a sales background, so they assume the best way to win business is by showing off all the cool features their product offers. They dive straight into long demonstrations, hoping the product’s value will speak for itself.
Here’s the catch: Most prospects don’t care about every single feature—they care about solutions to their specific problems. When you start with a demo, you risk overwhelming your audience. If the features don’t directly address their needs, you can lose their interest fast. Instead of feeling impressed, they might disconnect or feel frustrated. Plus, demo-heavy meetings leave little room for back-and-forth conversation, making it harder to uncover what the prospect truly needs.
The Power of Listening in Virtual Sales
The solution? Listen first, talk later. I was on a sales call recently and I wanted a demo of some software I was interested in purchasing. The salesperson stopped me and said let’s have a conversation first. He asked thoughtful questions about my situation and listened carefully to what I had to say. By the end of the conversation, I felt like he had truly understood my needs—and when it came time for the demo, I didn’t need it. I knew, without ever seeing a demo, that this product was exactly what I needed.
Listening works because it builds trust. When people feel heard, they’re more likely to believe that your product or service will fit their needs. Kick off conversations with open-ended questions like:
“What challenges are you facing with student engagement this year?”
“How have things changed since last year?”
“What would success look like for your team this year?”
These kinds of questions show that you care about their challenges—not just about closing a sale. And when you actively listen to their answers, it’s much easier to position your product as the right solution at the right time.
Shifting to “Confirmation Calls” Instead of Sales Pitches
One strategy I’ve found helpful is to reframe the first conversation as a “confirmation call” for myself. By the time a prospect books a call, they’ve usually interacted with my content—maybe they’ve read a blog post or seen something I shared on social media. Instead of using the call to pitch, I focus on figuring out if we’re a good fit.
During these calls, I stay away from solutions at the start. I focus on learning about their goals and challenges. It’s a two-way conversation we’re building a connection, building a relationship, we are not pitching yet.. The goal is simple: See if working together makes sense—no pressure. At that point people generally want to know how to work with me, and we move to the next call.
Letting Prospects Reach Their Own Conclusions
The next call is what I like to call the “self-identification” approach. This is where I walk potential clients through my nine-step process by asking them questions and auditing their process. I’ll ask questions like:
“What's your biggest challenge generating leads right now?
What's one thing you wish your current system could do better? ”
“Where do you feel stuck?”
“What’s missing from your current solution?”
These questions give the prospect space to identify their own gaps. And more often than not, by the end of the conversation, they realize on their own that my product is what they need. When people reach these conclusions themselves, they feel more confident in their decision—and there’s no need for a hard sell.
Telling Stories That Stick
If you tell great stories, you’re going to show real-world impact—and that impact will reflect positively on your business. Stories help people connect with you on a personal level. They don’t just show what your product can do; they give prospects a chance to see the results in action. When people hear real examples of how you’ve helped others, it makes it easier for them to overcome the hesitation they might feel about working with you.
Stories don’t just explain features—they show outcomes. They make your product or service relatable by putting it in the context of a real challenge and solution. And when prospects see that others like them have benefited from your solution, they’ll feel more confident in making a decision.
In the end, stories do more than just communicate value—they address objections, build trust, and guide prospects toward working with you. No matter what sales strategy you follow, the most important thing is to listen closely. When you truly understand your prospects, you can use stories to connect, add value, and handle objections naturally.
Why Listening Helps You Close Deals Faster
One of the biggest upsides to focusing on listening is that it actually speeds up the sales process. When you understand the prospect’s needs from the start, you avoid wasting time on features they don’t care about. Conversations become more targeted and productive.
Listening also reduces the chances of objections. When prospects feel heard and understood, they’re less likely to push back or ask for extra time to think things over. They feel more confident that your solution fits their needs, which makes it easier for them to move forward.
Key Takeaways for Selling in Today’s World
Build trust in virtual meetings by shifting from small talk to meaningful questions.
Skip the demo-first approach—listen to prospects before diving into product features.
Use open-ended questions to uncover real challenges and align your solution effectively.
Embrace a listening-first strategy to build trust and handle objections.
Tell real-world stories that demonstrate value and make your solution relatable.
Use confirmation calls to assess alignment early, saving time and effort.
Use Self-Identification Calls for them to identify their own gaps and allow them to see that your solution will help them.
Conclusion
Selling education products and services in today’s virtual world takes a different approach. The days of building rapport through in-person meetings and casual conversations are mostly gone, but you can still build meaningful connections—by focusing on listening.
Instead of leading with product demos, start by asking thoughtful questions about your prospect’s challenges and goals. Use your first calls to confirm if there’s a good fit, rather than jumping into a hard sell. And follow up with conversations that let prospects uncover their own needs and solutions.
In this new environment, listening is your most powerful tool. It builds trust, uncovers real needs, and makes prospects feel understood. When you focus on their challenges instead of your product, you’ll find that closing deals feels easier—and much more natural.