Why Most Founders Lose Deals They Should Have Won

Michael Bates
Oct 15
3 min read

The Question That Changed How I Listen — and How I Sell

For most of my career, I thought I was a good listener. I'd show up to every district meeting prepared—slides ready, ROI deck polished, talking points rehearsed.

I wasn't arrogant. I just wanted to prove I understood. But somewhere between "sharing insights" and "building rapport," I stopped listening.

I was hearing just enough to form a great response—not enough to truly understand what leaders were trying to tell me.

It took almost losing a million-dollar district deal to realize it.

The Moment Everything Shifted

We'd been in talks for months. Budget approved. Leadership aligned. Timeline locked.

It was supposed to be our closing meeting.

But something felt off. The superintendent wasn't making eye contact. The curriculum director kept circling the same questions. The energy in the room had changed—and I couldn't figure out why.

Old me would have gone into defense mode: reinforcing value, revisiting ROI, talking more to fill the silence.

But this time, I paused. Instead, I asked one question:

"What concerns haven't we fully addressed yet?"

That question changed everything. After a long silence, she told me what no one else had.

Years earlier, the district had rolled out a platform that frustrated teachers. Implementation stalled and created a visible conflict between teachers and administrators.

Her hesitation had nothing to do with our product. It was about trust—and not wanting to relive that experience.

So we rebuilt the implementation plan together:

A phased rollout starting with volunteer teachers.
Built-in feedback loops.
Monthly check-ins with teacher leads.

It became their plan.

The deal closed. But what stayed with me wasn't the sale. It was the lesson.

The objection someone voices is rarely the real one. The real objection sits just beneath the surface.

Listening Isn't Passive—It's Profitable

That meeting forced me to take a hard look at myself. How many times had I missed what someone was really saying because I was too focused on proving my point? How many relationships had I rushed—with the best of intentions—by trying to "add value" before earning trust?

I realized that most founders don't lose deals because their product isn't good enough. They fail because they're solving the wrong problem.

District leaders aren't begging for another solution. They're expecting someone to take the time to understand their reality:

√ Teachers stretched thin.

√ Budgets tightening.

√ Mandates shifting mid-year.

√ The pressure to do more with less, every single day.

You don't build understanding by talking. You build it by listening—deeply and intentionally. Not the kind of listening where you wait for your turn to speak, but the kind where you lean in, slow down, and let the silence do some of the work.

Because here's the truth, you don't close deals with data. You close them with understanding.

A Question for Founders

If you've ever walked out of a meeting thinking, "I nailed that presentation—why didn't they say yes?" you might have done what I used to do, answering questions no one asked.

Here's what I ask myself now before every major conversation: