Three Deals This Week: What I Observed Testing Different Approaches

I’ve been running informal experiments. Nothing scientific – just paying closer attention to what happens when I try different things in live deals. This week gave me three opportunities to observe, and the patterns are starting to get harder to ignore.

I’m not going to pretend these are controlled experiments. Sample size of three. Different buyers, different contexts, different stakes. But sometimes anecdotes reveal patterns that data obscures. Here’s what I saw.

Deal One: The One Where I Talked Less

Tuesday. Discovery call with a VP of Operations at a mid-market manufacturing company. Standard setup – they’d reached out after reading some content, wanted to learn more.

Normally, I’d run my standard discovery. Ask about their challenges, probe for pain, transition into how we might help. Lots of questions, but also lots of framing, lots of steering, lots of subtle positioning.

This time I tried something different. I asked one open question about what prompted the outreach and then… waited. Let the silence stretch. Didn’t rescue them from it.

What happened next was interesting. The VP started talking. And kept talking. For almost fifteen minutes, I barely said a word. He walked through their entire situation – the failed implementation last year, the pressure from the board, the political dynamics with his peer in IT, the timeline they were facing, the budget he’d already secured.

I didn’t extract this information. He volunteered it. By the end of the call, he was asking me how quickly we could start.

My talk time, according to the call recording: 23%. His: 77%.

Deal Two: The One Where I Pushed

Thursday. Third meeting with a Director of Sales at a SaaS company. We’d had two good conversations. He’d agreed there was a problem. He’d said the timing was right. All signals pointed to momentum.

I decided to push for commitment. Asked directly about next steps. Proposed a timeline. Suggested we get procurement involved. Did everything the playbook says to do when a deal is “ready.”

I watched him physically pull back. Not dramatically – he’s too polite for that – but I saw it. The lean-in became a lean-back. The engaged nodding became neutral listening. The energy shifted.

He said all the right things. “That makes sense.” “Let me think about it.” “I’ll circle back next week.” But something had changed. I’d felt it the moment I started pushing.

It’s been ten days. Two follow-up emails. No response. The deal that felt warm is now cold. I keep thinking about Jack Brehm’s research on psychological reactance – how people resist when they feel their autonomy is threatened. I’m wondering if that’s what I triggered.

Deal Three: The One Where I Almost Walked Away

Friday. A deal that had been stalled for six weeks. Classic pattern – initial enthusiasm, good discovery, strong demo, then… nothing. The champion kept rescheduling. The stakeholder meeting kept slipping. The deal was dying the slow death of endless delay.

I’d normally send another follow-up. Another “just checking in.” Another gentle nudge. Instead, I tried something that felt counterintuitive. I told them the truth.

“I get the sense the timing might not be right for this. If other priorities have taken over, I completely understand – it happens. I don’t want to keep bothering you if this has moved to the back burner. Should we close this out for now and reconnect when things settle down?”

I was genuinely prepared to walk away. I’d written off the deal in my head.

The response came within an hour. “No, don’t close it out. We’ve just been swamped. Can we get the stakeholder call on the calendar for next Tuesday?”

That call is now scheduled. Whether it actually happens remains to be seen. But a deal I’d mentally buried is suddenly showing signs of life – right after I stopped trying to revive it.

What I’m Noticing

Three deals. Three different approaches. Three different outcomes.

The deal where I talked the least closed the fastest. The deal where I pushed the hardest went cold. The deal where I offered to walk away came back to life.

I’m not drawing grand conclusions from a sample size of three. But I’m noticing a pattern that contradicts almost everything I was taught. More effort didn’t produce more results. Less pressure didn’t kill momentum – it might have created it.

Maybe this week was an anomaly. Maybe different buyers just responded differently. Maybe I’m seeing patterns that aren’t there.

Or maybe there’s something to this. Maybe the relationship between seller effort and buyer response isn’t what the training said it was.

I don’t have answers yet. Just observations. And a growing suspicion that I’ve been doing this wrong for a very long time.