Monday morning. Pipeline review. I’m not in this one – I was grabbing coffee in the kitchen area nearby. But I could hear most of it through the glass.
A sales manager was going through deals with his team. One by one. The same questions every time: “What’s the next step? When are they signing? What’s holding them back?”
And then, for almost every deal that wasn’t moving: “You need to push harder.”
Push harder. Follow up more. Be more persistent. Don’t let them off the hook. Create urgency.
I’ve heard this advice a thousand times. I’ve given it myself, if I’m being honest. It’s the default answer when deals stall. The assumption underneath is simple: if the deal isn’t moving, you’re not doing enough.
But lately I’ve been questioning that assumption. So I decided to watch.
The Experiment (Sort Of)
I don’t have access to this team’s CRM. I’m not their manager. But I sit close enough to hear things. And I’m nosy enough – or curious enough, depending on how you want to frame it – to pay attention.
So I just… watched. Over the next two weeks. Listened to the calls I could hear. Noticed the energy. Tracked what I could track.
This isn’t scientific. I know that. But sometimes patterns show up if you just pay attention.
What I Noticed
The reps pushed harder. They really did. More calls. More emails. More “just checking in” and “circling back” and “wanted to bump this to the top of your inbox.”
I heard one rep leave three voicemails for the same person in one week. Another sent a “breakup email” on Wednesday and then followed up again on Friday like it never happened.
They were doing exactly what they were told. More activity. More persistence. More push.
And here’s what happened to the deals:
Nothing good.
The Results
From what I could tell – and again, I’m piecing this together from overheard conversations and visible frustration – most of those stalled deals stayed stalled. A few went dark entirely. Buyers who had been somewhat responsive stopped responding at all.
I heard one rep say, “I think I burned that one. She asked me to stop emailing.”
Asked him to stop emailing. That’s not a stalled deal. That’s a dead one.
The next pipeline review – I happened to be getting coffee again – had a different tone. More deals pushed to next quarter. More “they went dark.” More frustration.
And the manager’s response? “We need to push harder on the new ones.”
I almost spit out my coffee.
The Definition of Insanity
There’s that old quote – probably misattributed to Einstein – about insanity being doing the same thing over and over and expecting different results.
That’s what I watched. Push harder didn’t work. The response? Push harder.
And here’s what kills me: nobody stopped to ask why pushing harder made things worse. Nobody questioned the fundamental assumption. The model says push, so we push. If pushing doesn’t work, we must not be pushing enough.
What if the model is wrong?
What I Think Is Actually Happening
I’ve been reading about something called reactance. It’s a psychological phenomenon – when people feel their freedom is being threatened, they push back. The harder you try to get them to do something, the more they resist doing it.
It’s why teenagers do the opposite of what their parents tell them. It’s why “don’t think about a pink elephant” makes you think about a pink elephant. It’s why pushy salespeople create resistant buyers.
I think that’s what I watched happen. The reps pushed harder. The buyers felt the pressure. And instead of moving forward, they pulled back. Went dark. Asked to stop being emailed.
The push created the resistance.
I Don’t Have The Answer Yet
I know what I saw. I don’t know what to do about it yet.
If “push harder” doesn’t work, what does? Let them ghost you? Give up? That doesn’t feel right either.
There has to be something in between. A way to stay engaged without creating pressure. A way to move deals forward without triggering that resistance response.
I’ve been experimenting with pulling back a little on my own deals. Being less available. Asking questions instead of providing answers. It feels weird. Counterintuitive. But some of the early results are interesting.
More on that later. For now, I just wanted to document what I observed.
Push harder.
It’s the answer to everything.
Except, apparently, it isn’t.
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