How to Follow Up With Prospects Like a Freakin’ Sales Rebel

Back in ancient Egypt and Mesopotamia, there was a class of people known as supplicants.

They were ordinary folks like peasants, farmers, and other citizens who would petition rulers and powerful officials for help.

They’d request justice for a wrong, intervention in a dispute, or more often, basic necessities like food and shelter.

The thing is, if you reach out to powerful officials these days and cross a line, the worst that usually happens is you get ignored.

But back then, you could end up imprisoned, or even executed.

So the stakes (and the nerves) were a lot higher.

Now, before we dive into the Rebellious follow-up principles, let me tell you about one very important peasant.

He went by many names, but for the sake of this blog, we’ll just call him Bob.

What a Peasant Can Teach You About Follow-Up

Bob lived in Salt Valley with his wife, Meret. One day, a wealthy landowner showed up, spotted his thriving crops, and decided he didn’t like the look of success.

So he beat Bob up, stole his grain and donkeys, and left him with nothing.

Brutal, right?

But instead of retaliating or giving up, Bob did something most modern-day sellers could learn from: he got intentional with his ask.

He knew that simply repeating, “Hey, give me back what’s mine,” wasn’t going to work. Everyone else was already doing that. And no one was listening.

So instead, he crafted an eloquent, poetic appeal. He used metaphors. He told a story. He didn’t just state the facts, but actually made people feel them.

And it worked. His words eventually reached a powerful steward who saw the injustice, punished the landowner, and restored everything Bob had lost.

Why is this story important? Because just like the powerful officials back then, your prospects get bombarded with requests every day: cold emails, connection pitches, follow-ups, voicemails, Slack messages, DMs, etc.

Most of them are saying the same thing, in the same way, using the same recycled lines. And just like those ancient rulers, they ignore most of them. Not because the messages are unimportant, but because they all sound the same.

So if you want to break through the noise and have your follow-ups actually land and get responded to, here’s what you need to know.

1. You’re talking to a stranger

Even if you’ve had a meeting with a prospect, exchanged a few emails, or sent over a proposal… you’re still just a stranger in their world.

That doesn’t mean they don’t like you. It just means they have no real connection to you yet. So don’t assume they owe you anything because they don’t.

Your job is to show up in a way that earns their attention, creates emotional context, and stirs curiosity around you and your offer.

2. Attention doesn’t mean interest

Just because someone opened your email, replied once, or said “circle back in two weeks” doesn’t mean they’re bought in.

There are levels to attention. Sometimes people respond because they’re curious, sometimes because they’re bored, and sometimes because you caught them at a weak moment between meetings.

Whatever the reason, you got their attention, but attention alone doesn’t move deals. Intentionality does.

Your follow-up needs to do more than just “check in.” It needs to deepen the connection, build trust, and open a real conversation.

3. Pattern interrupt

You’ve probably heard of pattern interrupt. And yes, it works. But here at The Rebellion we don’t treat it as just some psychological principle. We treat it like a way of life. A refusal to be mediocre.

Think about your prospect’s average day. How many messages, calls, and emails do they get? Now think about what those messages usually sound like:

• “Just checking in…”
• “Bumping this to the top of your inbox.”
• “Did you get a chance to read my last email?”
• “Thoughts?”
• “Is {insert dream outcome} no longer a priority for you?”

If you like getting ignored, that sequence is your best bet. But if you want to break the cycle, you’ve gotta show up different. You’ve gotta offer a better experience. The one they’re not expecting.

4. Communication = Relationship

Here’s the thing: it takes more than a couple of emails to get to the sale. It takes great conversations, great follow-ups, and great interactions that invite the prospect to share what’s actually going on.

And sometimes, the best way to do that is to simply be human. For example, send your prospect a handwritten thank-you note in the mail, but don’t mention “next steps.” Just thank them for their time.

Give them something they’re not used to getting. Something that makes them feel like a human being instead of a dollar sign.

If direct mail’s not an option, snap a picture of the note. Or record yourself holding it. The format doesn’t matter. The heart behind it does.

Because at the end of the day, your prospect’s a human being with a schedule, a family, a set of fears, goals, and pressures just like you. So prove they matter.

5. Play the long game (without being annoying)

Sometimes prospects disappear. But that’s just the reality of the game. So instead of hitting them with five messages that say the same thing in slightly different words, shift your mindset.

Stop thinking about follow-ups as reminders. Think about them as reignition of connection. As vehicles for continuing the story.

So when someone goes silent, don’t guilt-trip them with “Hey, I thought we had something.” Create a moment instead. A funny GIF, a thoughtful insight, a callback to something personal they said on your last call. Make them want to respond.

6. Good or bad… but never indifferent

The worst outcome in sales isn’t rejection. It’s indifference.

Some reps are so afraid of offending their prospect that they default to vanilla. They try to play it safe. Say what everyone else is saying. Do what everyone else is doing. And guess what? Do what everyone else does… get treated like everyone else does.

Now, we’re not saying to go full shock-jock. But we are saying this: you’d rather be remembered for being bold than forgotten for being boring.

So be good. Be bad. Be weird. Be honest. Just don’t be forgettable.

Final Thoughts

A good follow-up is about being pleasantly persistent. It’s about presence.

“I’m still here, and I still care. Not just about the deal, but about you.”

That’s what separates mediocre sellers from Rebels. We don’t send boring follow-ups. We send unforgettable ones.

And if you lack ideas and want help doing that, we’ve got a whole stack of Rebellious outreach campaigns ready for you at The Rebel Arcade.

Now go create a moment worth replying to.

Much love,

Dale