Sell to Gen-Z or Get Left on Read

Dale Carnegie published How to Win Friends and Influence People, a book that sold 30 million copies and trained generations of salespeople to make meaningful eye contact, remember birthdays, and ask people about themselves before asking them for money. It was, for its time, genuinely revolutionary advice, and it held up for decades.

A 24-year-old in your pipeline right now has never read it and would find the premise a little manipulative if they did.

This is gen-Z.

A Gen Z Character Study

Let's establish what we're actually dealing with, demographically.

Gen-Z is loosely, anyone born between 1997 and 2012, and they are the first generation to have grown up with the internet as a condition of reality. The internet, to gen-Z, is not a place you go, it’s actually a medium in which things simply exist. Asking them to remember a world before Google is like asking a fish to remember a world before water. The fish has never considered this. The fish does not find the question useful.

The practical consequence of growing up this way is that gen-Z has an extraordinarily high baseline for self-sufficiency.

The act of telephoning a stranger and asking for help is, to a gen-Z buyer, not a first resort or even a second resort. They call customer service only after they have consulted YouTube, Reddit, their group chat, and the kind of aggressive independent trial-and-error that would make their parents deeply nervous to watch.

So when this person enters a B2B sales process and someone tells them they'll need to sit through a capabilities overview before they can see the product, something happens behind their eyes. It is clinically undetectable, but it’s the exact expression of a sommelier being handed a juice box.

They Found The Reddit Thread. All Of Them.

Nobody says this out loud, but before a call, gen-Z buyers have already explained your product to themselves, at midnight, for fun, the way you might do a crossword. Gen-Z does this because they were raised in an information environment with essentially no friction, and they have spent their entire lives treating research as a form of entertainment.

By the time they're on a call with you, they are more of a researcher who has agreed to hear your side of the story than a prospect.

…and you opened with "so, where are you guys at in your journey?"

Carnegie's whole insight (ask questions, make people feel heard, let them talk) was genuinely brilliant, but it was also written in 1936 and for a world where the AE had information the buyer didn't. Essentially, that gap was the entire job.

The gap is gone and has been for a while. The only new development is that gen-Z showed up, looked around, and was the first one impolite enough to mention it. If gen-z already has the information you’re presenting on, your questions now just feel like stalling to them.

Being Seen Through Immediately

The other thing you should know about gen-Z buyers, which is equal parts impressive and slightly terrifying, is that they have a supernatural ability to detect inauthenticity.

Can you blame them though? These are people who were being algorithmically targeted before they had a driver's license. They’ve spent their entire lives swimming in sponsored content, influencer deals, and ads that knew what they wanted before they did.

The consequence of this, in a sales context, is that the standard playbook reads to a gen-Z buyer roughly the way a magic trick reads to a professional magician. They can immediately see the mechanism and are not entertained. So the discovery questions that "happen" to reveal exactly the pain points your product solves doesn’t move the needle anywhere.

The Advice You Scrolled Here For

Reframe where the sale actually starts. By the time a gen-Z buyer is on a call with you, the beginning has already happened so the discovery call is not the first date. It's more like the third date, and if you show up treating it like an introduction, you've probably misread the stage you're in.

Give them something to touch before you ask for their trust. A free trial, a sandbox, an interactive demo… anything that allows a person who is constitutionally inclined toward self-directed exploration to do some self-directed exploring. The amount of selling a gen-Z buyer will do to themselves, given access and five minutes of uninterrupted curiosity, is remarkable so let them poke at it and they'll show up to the next conversation having already closed half the distance.

Be a human on the call. Not a persona. Not a character from the playbook. Just be the human being who prepared for this call and is standing behind what they're saying. Gen-Z buyers are not hostile to sales people, but they are more hostile to performances. This distinction matters enormously and the line between them is thinner than most appreciate.

Your follow-up email is a test you don't know you're taking. "Just bumping this to the top of your inbox" reads as evidence that the recipient in a sequence and that you thought about them for roughly nine seconds. So instead, write something that requires human analysis and thought. Maybe a specific observation or simply just genuinely useful advice. Whatever it is, it should be enough to demonstrate that you are, in fact, a human (without making them solve a CAPTCHA to believe it).

If you're a gen-Z buyer or seller who somehow found this article, we know you already knew all of this. We just needed to say it for the people in the back.

If you're an AE who read this and felt seen, good. We want to empower you to be a human being on your next call because seriously, that's the secret.

And if you're a sales leader thinking about forwarding this to your team, do it! …but know that they've already read it, discussed it, and are waiting to see if you say "learnings" when you bring it up.

Please don't say learnings.