The Hidden Cost of Talking People Into Things

"I could talk anyone into getting that newspaper subscription."

Chuck Hill was describing his first sales job, going door-to-door in high school. He was good at it. Really good. The kind of good where you win contests and get promoted.

And then he learned what happened after the sale.

"But you know what would happen most of the time after you spend a lot of time talking someone into it? They cancel. And it becomes a chargeback."

That commission check he was expecting? Cut in half. Sometimes worse.

The Subscription Trap

Any business with recurring revenue—subscriptions, retainers, ongoing services—lives and dies by retention. And retention is determined long before the renewal date.

It's determined at the moment of sale.

If someone buys because they clearly understood their problem and believed your solution would fix it, they'll stick around long enough to find out. They'll implement properly. They'll give it a fair chance.

If someone buys because you convinced them, they bought your pitch—not your product. The moment the pitch wears off (and it always does), they start wondering if they made a mistake.

That doubt compounds. Every small friction point becomes evidence they were right to doubt. Every delay in results confirms their suspicion. The cancellation was inevitable from the first phone call.

The Real Estate Parallel

Tom Marcy sees this in real estate all the time. You can talk a hesitant seller into listing their house. But then:

"Those people cancel the listing. And you drive back and forth there like three times for different things—do the sign or the lock box or whatever—and then those people cancel anyway. Like how much time did that take?"

The math isn't just the lost commission. It's:

• The time spent convincing
• The time spent servicing
• The time spent on cancellation logistics
• The opportunities you missed while doing all of the above

A deal you had to talk someone into is rarely worth the time it takes to close it—let alone the time it takes when it falls apart.

Short-Term Revenue, Long-Term Drain

Let's say you run a $500/month service. A good salesperson can probably close an extra 2-3 hesitant customers per month by pushing harder.

That's $1,000-$1,500 in immediate monthly recurring revenue. Looks good on the dashboard.

But those customers:

• Cancel within 2-3 months (average churn for "convinced" customers is dramatically higher)
• Take 3x the support time while they're there (lots of questions, lots of doubt, lots of hand-holding)
• Sometimes dispute the charges on the way out
• Never refer anyone

Compare that to a customer who signed up because they had a clear problem and wanted your solution:

• Stays 12+ months on average
• Requires minimal support (they know why they're there)
• Pays on time without drama
• Refers 1-2 others like them

The "easy close" customer you had to convince nets you maybe $1,000 before they churn. The right-fit customer you didn't have to convince nets you $6,000+ and brings friends.

It Feels Like You're Losing

Here's the hard part: not convincing people feels like leaving money on the table.

You're sitting across from someone who's almost ready to say yes. A little more pressure, a few more objections handled, maybe a discount—and they'd sign.

But they'd sign as a convinced customer, not a confident one. And that distinction matters more than the immediate signature.

Chuck's advice: "Focus on the people who already admit that there's an issue to solve because we're in the problem-solving business. And they might have a problem to solve, but if they don't realize that, we got 10,000 more people that look just like you."

There are more customers out there. Customers who don't need convincing because they already feel the pain. Your job is to find them—not to create pain where none exists.

The Quality Signal

There's another benefit to refusing to convince: it changes how customers see you.

When you're willing to walk away, you signal confidence. You signal that you don't need this particular deal. You signal that your service is valuable enough that you can afford to be selective.

Paradoxically, this often makes the hesitant customer more interested. Scarcity and confidence are attractive.

But even if it doesn't close that particular deal, it positions you correctly for the next one. Word gets around. "Those guys don't take just anyone" is a better reputation than "those guys will say anything to close."

How to Stop Convincing

If you're used to pushing through objections and closing reluctant buyers, stopping feels wrong. Here's how to reframe it:

Redefine success. A "good" sales call isn't one that ends in a signature. It's one that ends in the right outcome—whether that's a new customer or a clear "not now."

Qualify earlier. Ask filtering questions before you pitch. "Is this problem something you're actively trying to solve right now, or is it more of a 'someday' thing?" The answer tells you whether to proceed.

Give them an out. Explicitly. "It sounds like the timing might not be right for this. Would it make sense to reconnect in a few months?" Many will take the out. Good. Better to know now.

Track the right metrics. Don't just measure close rate. Measure retention at 90 days, 6 months, 12 months. Segment by how "hard" the close was. You'll see the pattern.

Value your time. The hours you spend convincing one reluctant buyer could be spent finding three eager ones. Which is the better investment?

The Chargeback Test

Chuck has a simple heuristic: if you're seeing chargebacks or early cancellations, look back at how those deals closed.

Were they clear-eyed purchases by people who understood what they were buying? Or were they convincing jobs that felt like wins at the time?

The pattern is usually obvious. And it tells you exactly where your sales process is creating problems instead of solving them.

You can talk almost anyone into buying. The question is whether you should.

The customers you have to convince become the customers you have to keep convincing—until you can't anymore. The customers who convince themselves become the customers who stay.

Build your business on the second kind.