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How to Use Humor and Persistence in Follow-Ups Without Being Pushy

Most salespeople give up too soon.
They send a proposal, follow up once, maybe twice, and when the prospect doesn’t reply—they stop.

But here’s the truth:
People don’t buy because you followed up once.
They buy because you followed up again, and again, and again… in the right way.

So how do you stay persistent—without becoming annoying?

Let’s talk about how humor, tonality, and consistency can turn your follow-up game into a real closing machine.

Why You Must Follow Up Like a Maniac

According to the training, 9 out of 10 deals are lost due to poor follow-up, not because the offer wasn’t good.

Here’s what usually happens:

  1. Prospect gets the proposal.
  2. Salesperson calls the next day:
    “Did you get the proposal?”
  3. Prospect says: “I need to think about it. Call me back in two weeks.”
  4. Two weeks later, no answer.
  5. Salesperson stops.

That’s the default script most buyers have seen before.
They know: “If I ghost this person, they’ll go away.”
You must break that pattern.

You Are the Only Player on the Field

Even if the prospect told you they’re shopping around, act like you’re the only option.

Do not ask:

“How are things going with the other agencies?”

Instead, stay focused:

“Have you had a chance to review the proposal?”
“If the price was the same, who would you go with? Why?”

This frames the conversation around you and them, not the competition.
You keep the spotlight on your value.

Add Humor (Strategically)

When a prospect doesn’t pick up after several calls, here’s one line that stood out:

“Hey, it’s [Name] again. I feel like I’m building a real relationship with your voicemail… I might send it flowers next time.”

Why does this work?

  • It breaks tension.
  • It shows you’re persistent but not desperate.
  • It makes them smile—and makes you memorable.

You’re no longer another salesperson.
You’re the one who stood out with charm, not pressure.

Consistency Builds Admiration

Many prospects will ghost you simply because confrontation is uncomfortable.
They don’t want to say “no” directly—so they vanish.

But when they see you don’t give up after 2–3 tries, they start to think:

“Wow, this person actually cares.”
“They’re not going away.”
“Maybe I should respond.”

Persistence—when done well—builds respect.

Pro Tip: Set the Follow-Up Rhythm

Don’t ask:

“When should I call you back?”

Instead, say:

“I’ll send over the proposal and call you tomorrow—would 10 AM or 4 PM work better?”

This puts you in control.
It keeps the momentum going and avoids endless delays.

Final Thoughts

Being persistent doesn’t mean being annoying.
It means showing up with the right energy, timing, and tone—and sometimes, a little humor.

Because when others stop at the second voicemail, you’ll be the one still following up…
with confidence, clarity, and a smile in your voice.

Copyright © 2025 James The Marketer