The System That Makes Your Best Reps Look Like Kindergarteners

Same week, different conversations.

Last week, I watched Sarah - an enterprise AE prepare for a customer meeting like a chess grandmaster. She started with industry research, then company deep-dive, persona mapping, hypothesis building, and scenario planning.

“Great salespeople do the work outside the meeting,” she told me. “You’re anticipating anything that could happen.”

That same week, I heard three different sales leaders - A VP at a growth-stage company, a CRO at a late-stage startup, a GTM exec at a $25B software giant. All of them used nearly the exact same terms to describe their teams:

“Kindergarteners who need everything spoon-fed.”

“Coin-operated. Won’t do anything unless there’s immediate benefit.”

“No intrinsic motivation to learn.”

But here’s the thing: Both the scenarios can’t be true at the same time, but somehow they are.

The Analogy: The Hospital That Doesn’t Believe in Diagnosis

I’ve spent the last few months talking to a handful of sales leaders across growth-stage and enterprise companies. A strange pattern keeps showing up. Different markets, different products, different stages, but very similar enablement problems.

A GTM executive at that $25B enterprise software company (about 1,800 sellers; 3,500 field engineers) gave me the analogy that explained everything:

“We’re running enablement like a hospital that doesn’t believe in diagnosis. Twenty percent of patients struggle with one issue, so everyone gets that treatment. Thirty percent have something else? Everyone gets that treatment too. We keep adding medications without ever asking if THIS person needs THIS thing. The mortality rate stays high and we blame the patients.”

He calls it Peanut Butter Enablement - Basically spread everything across everyone and hope something sticks.

What really struck me is this company has all the right tools on papers:conversation intelligence, AI coaching, an Learning Management System(LMS), and a dedicated enablement team. And yet, as he put it “We genuinely don’t know who’s good at what.”

Last year their CRO spotted a critical gap. Their sellers were great talking to CIOs but couldn’t speak to line-of-business executives. So they invested/spent eighteen months building industry enablement. They partnered with every vertical team, created comprehensive materials, and integrated an AI coaching platform.

Then they mandated the training for all 1,800 people.

After all that work, they learned something uncomfortable.
”Many of them were already good at industry selling. We just didn’t know who.”

Think about Math for a second. If even 30% of those reps were already competent at industry selling, that’s 540 people who spent hours in training they didn’t need. Meanwhile, the 1,260 who actually needed help got the exact same generic content as everyone else. No personalization. No targeting. Just a very expensive hope that improvement would average out.

And what surprised me most is that this isn’t just an enterprise problem. The companies with the most resources are just as lost as the startups with spreadsheets.

What Happens When Your System Can’t Diagnose

Here’s a test: Without looking at quota attainment. Without asking managers to guess Just from observing behavior alone, can you tell me right now who’s in your team is struggling with:

• Deep discovery versus surface-level questions?
• Getting to economic buyers versus stuck with champions?
• Multithreading versus single-threading deals?
• Navigating procurement versus folding on first pushback?
• Industry conversations versus generic tech talk?

If you can’t answer these questions with confidence, you’re not really measuring sales skills. You’re measuring whether the sales reps still trust that enablement will help them.

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How Reps Learn When Systems Don’t Help Them

Here’s what Sarah has learned the hard way (the enterprise AE I watched):

Her Tuesday looks like this:
9am negotiation meeting with an enterprise healthcare account.
11am first discovery call with a fintech prospect.
1pm cold calling block across mixed industries.
3pm POC requirements review for retail.
4pm customer success check-in with manufacturing.

Five different contexts, five different companies. She needs to constantly do the context-switching between verticals, personas, and deal stages. And after every call, she is updating the CRM, sending the follow up emails, briefing internal stakeholders, and prepping for tomorrow’s meetings.

And in this chaos, Sarah learned a few things: battle cards go stale in three months. The LMS returns 1,500 unranked results when you search for anything useful. Role-play feels divorced from actual work. Training gets built for some mythical average rep who doesn’t exist.

So Sarah builds workarounds. She does her own research, finds top performers and asks them directly. She skips the official training because it’s failed her before.

To a manager who doesn’t see this work in the background(lets call it the invisible work), Sarah might look like someone going rogue, not following the process.But Sarah told me: “I love tools that help me get better. I’d use them all the time.I want AI coaching, role-plays, and personalized feedback.

She’s not resistant to learning. She’s just resistant to wasting time on things that don’t help.

That’s not kindergartener behavior. That’s sophisticated pattern-matching from someone who learned the system doesn’t support her.

When Coaching Becomes Random, Fear Becomes Rational

I’ve been selling for the first time in my career this year. The thing that surprised me most is that the biggest blocker isn’t knowledge, It’s actually fear.

Fear shows up camouflaged:

• “I don’t have the vertical expertise” which actually means fear of looking stupid
• “I was being nice to the customer” which actually means fear of losing the relationship
• “I didn’t feel comfortable pushing harder” which actually means fear of their reaction

This is where Sarah’s behavior starts to make even more sense. For instance, Sarah’s real advantage isn’t that she’s smarter than the other reps. It’s that she has confidence. She can qualify hard, get to power players, ask uncomfortable questions, and build champions who do the work for her even when she’s not in the room.

But that confidence came from somewhere. Early wins that build momentum. Good coaching at her first company. Safe practice environment where failure didn’t cost deals and doesn’t invite judgement.

Here’s the connection most sales leaders miss: when systems can’t diagnose problems, coaching becomes random. Random coaching often creates fear because reps can’t predict what “good” looks like.
And when reps stop trusting the system, something else quietly takes over: self-protection.

So they get cautious.

Generic enablement doesn’t address much when the real barrier is emotional. AI role-plays without context don’t build confidence. And battle cards don’t help when you’re scared to use them.

What looks like “no intrinsic motivation” from outside is actually learned helplessness from systems that promised transformation and delivered theater.

How System Failures Turn Into A Death Spiral

When enough reps start operating in self-protection mode, the problem stops being individual and becomes organizational. Each failed tool compounds the diagnosis problem and the rep starts believing: it. “maybe I’m the problem.”

Let’s take a look at how it pans out in reality.

That growth-stage VP? His reps are using Claude for call coaching. It’s a smart idea, but adoption is “inconsistent” because it’s not official. Only the experimenters found it.

The enterprise company? It has five different tools that don’t integrate. The CRO says: “We spent a boatload. If someone gave us one platform that actually worked, there’s no shortage of dollars.”

But leadership hesitates because reps don’t make the most of the tools provided to them and makes it difficult for them to justify the investments.

And reps don’t use tools because they’ve been burned too many times.

The cycle repeats and reinforces itself. Round and Round it goes.

If you can’t diagnose, you can’t really enable. You can only broadcast. And broadcasting is how organizations end up blaming individuals for outcomes the system quietly created.

The label sticks: kindergarteners.

The Uncomfortable Truth: It’s Not Talent, It’s Luck.

Here’s the part I often think about: Elite performers aren’t a different species.They’re often the people the system happened to work for in their early careers. They tasted early wins that built confidence before fear could calcify. They got good coaching when they started (rare, because managers are stretched). They had time to develop habits before pressure ramped up.

Everyone else? They get generic training, tools “on the side,” outdated content, and managers too busy to help them.

The difference isn’t talent. It’s luck. It’s the system’s randomness that happened to break in their favor. And that should bother you. Because here’s what a system with actual diagnosis would reveal:

Let’s go back to Sarah’s preparation ritual at the beginning of this post. That’s not just her being exceptional. That’s a learnable behavior pattern - remaining on top of the Industry research, company analysis, hypothesis building, and scenario planning. Those are discrete and coachable skills that you could identify and measure

But to enable this, you’d need to know who’s already doing them and who isn’t. Right now, you’re giving Sarah the same “how to prepare for meetings” training as to the rep who shows up cold to every call. One of them is wasting their time and the other is developing bad habits because they’re not being pushed.

Neither outcome is good.

What to Actually Do About this

I’m not saying hire better people or invest in more tools.I’m saying build systems that can diagnose.

Stop identifying the best rep based on quota attainment. Stop asking managers to estimate who’s good at what. Stop giving everyone everything and hoping it sticks. Stop the Peanut Butter Enablement.

Instead, start with something simple: track one behavioral signal this week. Not quota attainment. Not activity metrics. Pick one skill from that test above (multithreading, deep discovery, executive access) and just watch who actually does what it in their calls.

Don’t build a dashboard yet. Don’t buy a tool. Just notice the pattern.

That’s a diagnosis. Everything else follows from there.

The technology exists to do this at scale now. But until we deploy it properly, we’ll keep running hospitals that don’t believe in diagnosis. We’ll watch the mortality rate stay high and blame the patients. And we will keep on producing Kindergarteners and make the smart, competent, and capable people end up looking like they need to be spoon-fed.

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Where does enablement break first in your org?
I’m collecting stories from sales leaders. Drop a comment or DM me.

Next week: Why even companies who solve diagnosis still can’t make enablement work. You can’t feed an ocean through a straw, no matter how good your straw is.