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• Identify and validate PMF in the field

• Build a repeatable customer acquisition motion from lead to close

• Gain the confidence and certainty to close deals with predictablity

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Title: Why Deals Go Dark (and how to stop it)

Read time: 3 min


Today, we’re talking about one of the least sexy, least talked-about, but most decisive skills in sales: follow-up.

I read posts constantly on LI that suggest success in sales comes from the perfect pitch, the killer demo, or the magical one-liner that flips a prospect.

Here’s the truth: most deals are won or lost in the follow-up.

Not because you “pinged” someone one more time. But because of how you follow up and the language you use.

If you want to build a GTM sales led motion that can’t be denied, stop thinking of follow-up as a polite nudge and start treating it as a weapon.

After watching hundreds of founders fail and succeed, I’ve seen this pattern over and over. The best are methodical and unafraid in their messaging. I’d rather a have prospect tell me to fuck off than live in sales purgatory for 6 months.

The individual who moves a mountain begins by carrying away small stones.

~ Confucius

In founder-led sales, the ones who win aren’t the ones with the perfect pitch/product.
They’re the ones who keep showing up long after everyone else has gone quiet.

Here’s how to build the kind of persistence that turns silence into progress and interest into closed wons:

1. Follow-up is a signal of leadership

I see many founders who believe they lose deals because of timing, budget, or a competitor, which is true, but in reality, it’s much deeper. Most deals die because no one is driving.

After the first call, they stop pushing. They confuse being passive with being professional. They wait for the buyer to make the next move. A stalled deal isn’t the buyer’s fault. It’s a leadership, or lack thereof problem. In last weeks issue I discussed mindset and why many founders are actually afraid to close deals.

Persistence and process is what keeps momentum alive. It’s structure, clarity, and showing that this matters enough to keep moving forward. It’s about demonstrating you care enough to own the next step.

2. Build a proper follow-up system

Follow-up fails when it’s random. When you “just check in” because you remembered to.

The killers know exactly what happens next before they leave a meeting:

• When is the next meeting, scheduled with a day and time on the cal?

• What is supposed to happen between now and then?

• What decision will be made on that call?

That clarity eliminates 90% of the ghosting problem.

For the remaining 10%? That’s where your follow-up process kicks in:

• Calendar reminders.

• CRM tasks.

• Sequences that don’t just poke, they move the ball forward with every message.

If you’re relying on memory, you’ve already lost.

3. Persistence is a filter

Founders often tell me, “I don’t want to be annoying.”

But think about your own buying behavior: if someone gives up after one or two touches, you weren’t that interested to begin with.

Persistence filters out the unserious. The ones worth winning are busy, distracted, and skeptical. They need you to break through.

It’s not persistence for persistence’s sake. It’s intentional:

• Every touch adds clarity.

• Every touch reduces friction.

• Every touch gives them a reason to engage.

When you stop too early, you give yourself a false signal: “They weren’t interested.” No. You just weren’t persistent enough to make it matter.

4. Make your follow-ups valuable, not needy

Bad follow-ups are just noise: “Hey, just checking in.”

Great follow-ups advance the conversation:

• A clear recap of the last call

• A short insight you promised

• A reference story they can relate to

• A next step to lock in

Each touch is validation that working with you will feel structured, clear, and worth their time.

When your follow-ups add value, the buyer starts to look forward to your messages because you’re helping them think, not just reminding them you exist.

5. Build emotional stamina for the silence

The hardest part of follow-up isn’t writing the email. It’s managing the anxiety that comes with no response. Even me, and I’m totally aware of it.

You start making up stories:

• “They’re not interested.”

• “I pushed too hard.”

• “I’ll look desperate.”

That’s the noise that makes you get soft. They stop sending. They pull back instead of leaning in.

You need to train yourself out of this reflex.

Silence doesn’t mean no. It means busy. It means not a priority yet. It means your job is to make it a priority.

Key Takeaway

Follow-up is not a courtesy. It’s a discipline.

Every deal that drifts, every “ghosted” prospect, every great first call that dies, it’s almost always a failure of follow-up.

Decide that you will be un-ignorable. Be the founder who leads, not the one who waits.

When you do, your close rate jumps, not because your pitch got better, but because you stopped leaving deals to chance. 💪



That’s it for today folks.

See you all next week!

Darren

P.S. If you’re a venture-backed company interested in coaching, book a call here.