The education landscape has changed dramatically post-pandemic. School districts, stretched thin on financial and human resources, are more wary of edtech pitches and promises. After years of stimulus-fueled tech spending and mixed results, they’re looking for partners who truly understand their needs.
Trust and credibility have never been more important for edtech founders. On sales calls, this starts with active listening, establishing authentic connection, and demonstrating a genuine understanding of your prospect’s day-to-day challenges. Beyond the specific problem your business solves, strive to also understand the conditions they must work through — multiple budget owners, procurement processes, leadership transitions and others.
Done well, this not only unlocks business opportunities, but also lays the foundation and knowledge base for scaling your sales function effectively.
Drawing from discussions with veteran education sales leaders and founders, here are essential strategies for conducting discovery calls that build lasting trust with decision-makers.
The Do’s
Start with who you are, not what you sell
Education buyers are emotional buyers. They need to trust not just your product, but your purpose. Just as good classroom teachers build rapport with students before diving into lessons, take time to establish the founding story of the business and what inspired you to take the leap. This not only helps you deliver your message more effectively, but makes you stand apart from the transactional sellers that solicit them all day.
What’s your story? Where do you come from? Why are you here? What led you to build this product? What have you learned about the process? Questions like these about your lived experiences go a long way toward building credibility. Stories build trust more effectively than specs.
Let them do the talking
The best discovery calls have the prospects doing most of the speaking. Avoid asking yes/no questions. Instead, lean into open-ended, probing ones like “What feedback do you get from end users that seems repetitive?” or “What is something you really wish you had that current solutions don’t provide?” Finding specific, granular questions that point to what is motivating them to pursue a solution is key to the context-gathering process. Over time, you’ll build a mental model for which questions generate the most valuable, qualifying answers.
Those moments of thoughtful silence as they consider their response? That’s where the real insights emerge. Responses that follow a prolonged pause can be gold, for they are likely to be authentic, honest, and more revealing for how they want to proceed.
Elevate the prospect
The best salespeople excel at elevating the prospect. Education buyers, particularly at the middle management levels, are rarely recognized for the hard (and often thankless) job they do. Be deeply curious about their day-to-day. Lean on them as someone who can share more depth about the problem you’re aiming to solve.
This part of the conversation can unlock new product opportunities or pivots. Patterns may emerge around edge cases that get more to the heart of the problem for your buyers. (“We thought this was the problem, but this is what they are really struggling with!”) Giving your prospects a platform to share what they know about the work can help you refine your value proposition in the long run.
Do your homework
Districts appreciate when you understand their world enough to anticipate challenges. Research their unique context: the student demographics, the board’s strategic initiatives, existing technology stack. Track RSS feeds from flagship districts that have outsized influence. Stay current on policy changes that might affect them. But demonstrate this knowledge subtly through informed questions, rather than rattling off facts.
Staying on top of research also provides authentic opportunities for ongoing engagement beyond generic check-in requests. Tracking district changes and policy updates offers a genuine way to keep in touch, such as sharing how similar schools are handling new challenges, flagging relevant shifts on the horizon, or connecting them with peers tackling similar problems. Let them know you’re keeping them top of mind — and they may just return the favor sometime down the line.
The Don’ts
Don’t rush to demo
The impulse to show off your solution is strong, but resist it. Some successful companies won’t even do demos without a qualifying conversation first. Understanding fit matters more than features. When prospects demand “Just show me how it works,” it can be a yellow flag for a customer who doesn’t necessarily care about whether the product is right. This is the earliest churn risk indicator of them all.
Explain that you want to ensure your solution truly addresses their specific needs first. It may feel like reverse psychology since these calls are often primed for demos. Be selective: Let the discovery process shape the demo, not the other way around.
Don’t assume one size fits all
Districts see themselves as unique, with good reason. An urban principal in one state faces dramatically different challenges than a rural one in another — from student demographics and available resources to specific community needs and political pressures. Even those with similar profiles may have completely different strategic priorities or technical infrastructure.
When sharing success stories, focus on the problems solved and implementation approaches. Refrain from simply name-dropping customers (which can sometimes backfire.) Effective sales conversations should demonstrate an understanding of each district’s nuanced circumstances and how your solution can adapt to them, rather than suggesting what worked in one place will automatically translate to another.
Don’t gloss over implementation
Education buyers have been burned before by tools that demo well but fail in practice. Address how you’ll handle training, technical setup, adoption, and ongoing user support. After all, they are putting their credibility on the line. Be prepared to discuss specific change management plans, resource requirements, and timelines. Nothing builds trust like showing you’ve thought through the practical realities of getting your solution working in the chaos of a live classroom environment.
Don’t fill the silence
When you ask a thoughtful question, give them space to think deeply about their response. The natural impulse is to jump in and guide them to an answer, but that’s exactly when you should stay quiet and listen. Top sales leaders know how to use these contemplative pauses to get the most valuable insights about customer needs. If you’re constantly talking, you’re missing crucial information.
How Do I Know If I’m Getting Better at This?
There are two key signals:
- Hit rate. While every business is different, based on contract sizes and acquisition motion, enterprise sales shouldn’t take much more than 6-8 discovery calls with prospects who match your ideal customer profile (ICP) to close a deal. If you consistently need more, an adjustment is warranted. Perhaps your ICP definition needs tightening, your buyer-versus-user value proposition is poorly aligned, or you’re not qualifying leads well enough upfront.
- “Golden questions” library. The signal is more nuanced but equally important: after several months of sales conversations, you should have a set of questions that make prospects pause, laugh, or otherwise react thoughtfully because you’ve hit on something that really matters to them. Questions they don’t get from competitors that show an appreciation for the nuances they operate through each day. These questions become your secret weapon that help guide conversations toward your value proposition. The best sales pros can read the room and know exactly when to deploy them for maximum impact.
