Sales People Need to Go Back to Kindergarten

Ever crushed a pitch and got nothing back but confused looks?

It happens all the time. You say all the right things, list the key benefits, back it up with data — and it still doesn’t land. Not because you’re wrong. Not because your product isn’t valuable. But because the message got lost in translation.

The best sales pros aren’t just product experts — they’re experts in communication and reading the room. They know how to adjust their message based on who they’re talking to and how that person is reacting. Most reps don’t. They stick to one pitch, one version of the story, and just hope it hits.

But value doesn’t change — the way you explain it does.

Same Value, Different Language

Some buyers are at a kindergarten level when it comes to understanding your space. That’s not a dig — it’s reality. They might be leaders in their role, but your product or category could be completely new to them. You — if you’re doing your job — should be operating at a high school or college level.

Your job isn’t to impress. It’s to translate. To make it click. That might mean simplifying, using analogies, or changing your pace — whatever gets through.

It’s the same value, but you need to be able to say it five different ways depending on who’s in front of you and what they’re saying.

Know Who You’re Talking To

Great sales people can size someone up fast. Are they new to the space? Are they informed? Do they think they’re informed but actually have a flawed understanding?

I used to sell programmatic recruitment software — a disruptive model at the time. A lot of the HR and TA execs I spoke with were sharp, experienced leaders. But when it came to programmatic, most hadn’t seen it before. We had to keep it simple — kindergarten level, even for C-levels. As the space matured, we started working with true experts who wanted to talk strategy, measurement, optimization.

Same product. Same value. Totally different pitch.

Validate Your Pre-Call Prep

This is where most reps fall flat — they don’t frame their message around what the buyer understands. They jump straight into the deck or demo with no adjustment. If you want your message to land, you need to meet the buyer at their level, then bring them up to yours.

Sometimes that means testing three versions of your pitch in the same call. It’s not a formula — it’s a dance. You shift your tone, language, and story until it clicks.

And don’t assume your pre-call prep is correct. Framing the conversation at the start of the call is a skill of its own.

Don’t Skip Kindergarten

This isn’t about dumbing things down. It’s about respect — for your buyer’s context, perspective, and level of understanding. You’re not there to talk at them. You’re there to help them get it.

The best sales pros aren’t locked into a script. They’re fluid. They pivot, simplify, and elevate as needed. They make sure they’re dancing to the beat of their prospect — not their own.

So go back to kindergarten, elementary or high-school when it makes sense. That’s how deals get done.