The Tax Nobody's Talking About

Woke up this morning, saw a good LinkedIn post, fresh off the press and said, oh SNAP, need to jump on this one!

So, here is today’s newsletter fresh from fresh of ideas.

Brandon (CEO of Seamless.ai) wrote about “how most follow-ups are killing deals. Not because reps aren't persistent—but because every "just checking in" is a tax on busy buyers.”

For the record, I think he’s great.

His point: messages like "any thoughts?" or "bumping this" force buyers to remember context, reconstruct the conversation, and do the work. When buyers are slammed, silence becomes the easiest response.

He's absolutely right.

But there's a heavier tax he didn't mention, the one on the seller.

The seller's burden…

This is what most reps are wrestling with on every single deal.

What do I send next? In what context? At what stage? Toward what milestone?

Not every team has sales enablement. Not every org provides playbooks, templates, or decision frameworks.

So reps are left creating every follow-up from scratch. They have to…

-Recall the last conversation

-Remember the key insight

-Map it to the buyer's stage

-Figure out the logical next step

-Package it all cleanly

That's exhausting. And when people are overwhelmed, they default to the path of least resistance…the FAMOUS, TADAAA …"Just checking in." "Bumping this." "Any thoughts?"

Forget laziness. They're stuck! It’s a BIG FRIGGIN skill gap and a time suck.

The real problem is while buyers are being taxed with low value follow ups, sellers are being taxed with decision fatigue and creative overload.

And when you don't know what comes next, you hesitate. You delay. Momentum burns out.

Throw the persistence piece and conversation out for this context. Try competence and having the structure and support to know what the right next move actually is.

What a better follow up could look like…

These three things:

-Reconnect the context, "When we talked, you mentioned [specific pain point]"

-Name the next decision, "The next step is choosing between [Option A] or [Option B]"

-Make it easy to respond, "Which approach fits better with how your team evaluates [X]?"

Here's an example…

Bogus- "Just checking in, any thoughts on the proposal?"

Better- "You mentioned your team struggles with manual data entry eating up 10+ hours a week. The decision now is whether to pilot this with one team or roll it out company-wide. Most teams in your situation start small to prove ROI first. Does that match your thinking, or would a broader rollout make more sense given your Q2 deadline?"

See the difference?

That’s one layer. Now enhance it. Package it in some way that WOW the recipient.

Like this file below - this is what I sent to celebrities after our first phone or zoom interaction to clarify and build additional value in and map the opportunity (be known there are quite literally dozens of various situations to create something like this)

The first approach makes the buyer do all the work. The second is a step in the right direction and shows you were listening, frames the decision clearly, and gives them an easy on ramp to reply PLUS demonstrating a standard.

The solution isn't "write better emails."

It's giving yourself the structure to write better emails without reinventing the wheel every time.

Meaning, stage specific playbooks that map buyer journey to next steps.

Follow-up templates with smart customization prompts.

Tools that surface conversation history and suggest what to send next.

When you have this, you’ve got leverage and spend 2 minutes personalizing instead of 20 minutes staring at a blank screen.

Bottom line…

If you're thinking "Yeah, I know just checking in sucks, but I don't know what else to send you need some structure.

Fix the seller tax, and the buyer tax fixes itself.

See you next week, Follow Up Fam.

Manny "That Follow Up Guy" Vargas