Why Understanding People Closes More Deals Than Perfect Presentations

Not listening and paying attention to body language cost me a deal.

The curriculum director was telling me about her teachers burning out. Thirty kids per class. Multiple different reading levels. No time for intervention.

I kept trying to convince her with features and benefits: adaptive remediation, real-time, data-driven decision-making, and integration with the district SIS.

She finally stopped me: I hear what you're saying. But that's not what I need right now. I need an empathic partner who understands what we're actually dealing with.

Unfortunately, I lost the deal.

Not because our product was wrong. Because I wasn't emotionally present to what she was actually saying.

What I Didn't Understand About Sales

Early in my career, I was taught that closing meant convincing.

• Build the best slide deck. 

• Know your competitive advantages. 

• Handle objections smoothly. 

• Show ROI clearly.

Master those things, I was told, and you'll win deals.

So I did. I built impressive presentations. I memorized responses to common objections. I could talk about our product's capabilities for hours.

And I lost deals to competitors who weren't as polished. Whose products weren't as sophisticated. Whose presentations were half as impressive as mine.

That's when I started paying attention to what was actually happening in sales conversations.

The Pattern I Kept Missing

Here's what I noticed when I finally started watching instead of just performing:

The deals I won weren't because I had the best answers. They were because I picked up on things others missed.

The hesitation in a superintendent's voice when talking about board support—telling me the real obstacle wasn't budget, it was politics.

The frustration in an administrator's description of their current system—revealing that the problem wasn't features, it was implementation fatigue.

The exhaustion behind a curriculum director's question about timelines—showing me that capacity, not capability, was the real concern.

Those emotional cues told me what the real problem was—not just the stated problem.

And when you understand the emotional reality behind the business problem, you can address both.

What Emotional Intelligence Actually Looks Like in Sales

The education community calls this Behavioral Health Literacy—the ability to recognize and respond to the emotional and mental health of a situation.

In sales, it means being present to what someone's actually communicating, not just what they're saying.

It's the difference between hearing, “We need better data”, to hearing, “Our teachers are drowning in data they don't have time to use, and our administration is demanding proof of impact.”

Same words. Completely different problems.

When I was only listening to the words, I'd launch into a demo of our analytics dashboard. Look at all these reports you can generate. See how easy it is to track student progress. Here's how you customize the views.

The curriculum director would nod politely. Then go quiet.

When I started listening to the emotional reality—the overwhelm, the time constraints, the pressure they were under—I asked different questions:

• Help me understand what happens when teachers get this data. Do they have time to act on it?

• When the administration asks for proof of impact, what are they really asking for?

• What would success actually look like for your teachers?

Questions like these open conversations because they acknowledge the human reality, not just the problem.

The Three Signals I Missed for Years

Looking back at deals I lost, I can now see three emotional signals I consistently missed:

The curriculum director who kept circling back to implementation timelines. I thought she was worried about our deployment process. She was actually worried about teacher capacity. Her teachers were already overwhelmed. Adding one more thing—even a helpful thing—felt like drowning them further.

The superintendent who asked repeatedly about board optics. I thought he was worried about looking good. He was actually managing complex political relationships. The board had competing priorities and factions. He needed a solution that different board members could support for different reasons.

The principal who wanted extensive proof it works. I thought she was being overly cautious. As it turned out, she'd been burned before. A previous vendor had promised transformation and delivered chaos. She wasn't evaluating our product. She was evaluating whether she could trust us not to make her situation worse.

When I responded to their words instead of their emotional reality, I lost all three deals.

When I started responding to what they were actually worried about—not just what they were asking about—conversations changed completely.

What Changed When I Started Paying Attention

Once I started tuning into emotional cues instead of just waiting for my turn to talk, everything shifted.

Conversations became easier. Not because I got better at talking, but because I got better at listening.

I stopped trying to convince people and started trying to understand them.

I stopped treating objections as obstacles to overcome and started treating them as information to explore.

I stopped running through features and started solving problems—including the emotional and political problems that weren't written in the RFP.

The deals I win now aren't because I have the best presentation. They're because I understand their actual situation before I say anything about my solution.

That's not manipulation. That's just being present to what someone's actually communicating.

It builds relationships that last beyond a single contract.

And it's the difference between listing features and solving problems.

Why This Matters More Now

Here's what I've noticed post-pandemic: district leaders aren't just managing budgets and programs anymore. They're managing exhaustion.

Teacher burnout. Student mental health crises. Parent frustration. Staff shortages. Constant disruptions.

When I show up with another solution that requires more time, more training, more change management, I'm not helping. I'm adding to the problem.

But when I show up with understanding of what they're actually dealing with—not just the technical challenge, but the human reality—everything changes.

I can help them think through implementation in ways that don't overwhelm their staff.

I can position solutions in ways that build board support instead of creating political problems.

I can be honest about what our product will and won't solve, which builds trust instead of creating future disappointment.

That's not soft skills. That's a strategic advantage.

What I Still Get Wrong

Even now, with decades of experience, I mess this up.

I talk when I should listen. I miss cues. I fall back into presenting mode when I should be in discovery mode.

It happens when I'm feeling pressure to move deals forward. When I'm anxious about the pipeline. When I'm so focused on what I want to say that I stop being present to what they're actually communicating.

But when I catch myself and reset—when I stop performing and start being present—conversations get better immediately.

The curriculum director, who seemed resistant, suddenly opens up about what's really concerning her.

The superintendent, who was being vague, suddenly shares the political dynamics he's navigating.

The principal, who was stalling, suddenly explains what she needs to feel confident moving forward.

Not because I said something brilliant. Because I finally shut up and listened.

The Questions That Changed Everything

After years of trial and error, I've learned there are questions that open doors and questions that close them.

Questions that close doors sound like sales disguised as questions:

1. Would you be interested in a solution that improves reading scores?

2. Are you looking for better data usage?

3. These are leading questions. Everyone knows you're trying to steer toward your product.

Questions that open doors sound like genuine curiosity:

1. What's your number one challenge with reading intervention right now?

2. When you think about next year's budget priorities, what concerns you most?

3. Help me understand what's working and what's not with your current approach.

These questions don't include your product. They're about their world, not yours.

When you ask about their problems without an agenda, people actually tell you the truth.

When they sense you're just trying to sell, they give you polite answers and move on.

What This Means for You

If you're an EdTech founder struggling to close deals, ask yourself:

Are you listening to what people are saying, or are you hearing what they're actually worried about?

Can you name the emotional and political realities your buyers are navigating, or are you only thinking about the technical problems your product solves?

Do you pick up on hesitation, frustration, and exhaustion in conversations, or are you so focused on your presentation that you miss the signals?

When someone asks a question, do you answer what they asked, or do you explore why they're asking?

These aren't comfortable questions. I avoided them for years because I thought emotional intelligence was a soft skill that didn't matter in B2B sales.

I was wrong.

Emotional intelligence isn't soft. It's strategic.

It's what separates vendors who list features from partners who solve problems.

It's what builds relationships that last beyond a single contract.

And it's what closes deals when your product isn't perfect and your presentation isn't polished.

Because at the end of the day, people don't buy from the vendor with the best slide deck.

They buy from the person who actually understands what they're dealing with.

What emotional cues do you pay attention to in sales conversations? I'm curious what signals others have learned to watch for.