Why Traditional L&D Models Fail (And How to Actually Build Real Expertise)
Most L&D is a Bureaucratic Placebo
Corporate training has become a box to check, a theater of development that makes companies feel like they’re investing in their people but ultimately achieves little. A bureaucratic placebo, if you will.
At best, it produces workers who can follow a script but aren’t empowered to think beyond it. At worst, it actively stifles the very expertise it claims to build. And if all we’re doing is creating roles that rely solely on step-by-step execution, we’re not future-proofing our workforce—we’re designing jobs that AI will inevitably replace.
To be fair, in huge, slow-moving enterprises, structured training has its place. Charter Communications has over 100,000 employees — during my tenure we merged three telecom giants (and three L&D and Enablement teams) into one. We needed standardized training to make sure frontline workers could handle repeatable, high-volume tasks. That kind of structure makes sense in a company of that scale — but again, my bet is telecom sales and support will be largely outsourced to AI before it's all said and done.
The biggest problem I see is the same L&D model that might be marginally useful at the slow-moving, scaled workforce of 100,000 gets applied to dynamic, fast-moving organizations — where it doesn’t belong. The result is a false sense of control. L&D and "Enablement" becomes a self-justifying machine, where teams build endless frameworks and certifications that make zero difference to actual performance.
And in those environments, the placebo stops working. If you want your workforce to be highly adaptable, deeply skilled, and truly capable of solving complex problems, then you need a radically different approach.
Traditional Models Fail in High-Growth, Dynamic Organizations
L&D and enablement teams love structure. They love models. They love frameworks.
They love to turn human development into a process, a set of steps, a perfect sequence of checkboxes that somehow, magically, will produce a high-performing workforce.
The fundamental problem with this is that structured training assumes a fixed, static reality. But if you work at a company that’s dynamic and constantly evolving—where the product, the market, the competition, and the customer demands are shifting all the time—then that approach is wildly inefficient. And more than that...
It’s actively destructive.
Most sales enablement and training programs rely on:
❌ Spoon-feeding information instead of fostering curiosity and ownership.
❌ Static certifications that are obsolete the moment the company iterates.
❌ Over-engineered learning frameworks that look great in theory but fail in practice.
❌ A false belief that training = capability. (It doesn’t.)
But here’s the truth: Expertise isn’t built in training rooms. It’s built in the real world, through friction, failure, and iteration.
Learning Happens in the Trenches, Not in a Classroom
Let’s be honest... most corporate training is a joke.
It doesn’t change behavior. It doesn’t create experts. At best, it creates people who can answer multiple-choice questions on a test.
Take mandatory compliance training—like sexual harassment modules. These aren’t about teaching people anything. They exist so the company can say, “See? We told them not to harass anyone. If they do, it’s on them, not us.”
That’s not training. That’s corporate legal cover. And it’s a perfect example of how much of L&D is designed to protect the company, not develop the people.
Now, does that mean structured content has no place? Of course not. But sometimes, the most effective way to learn something is just getting the information, quickly and clearly, and then trying it yourself.
If I need to fix a leaky pipe, I don’t want an interactive e-learning module, a four-step simulation, and a “safe practice environment” before I actually touch the damn pipe. I just want a YouTube video or a simple guide that tells me what I need to know so I can get under the sink and try it. Maybe I’ll pause and check back if I get stuck. Maybe I’ll ask someone for help. But the actual learning happens when I do it.
The problem is that corporate L&D rarely operates this way. Instead of giving people simple, effective resources, it tries to engineer elaborate “learning journeys”—forcing employees through rigid programs, unnecessary certifications, and endless training sessions when all they really needed was the answer, a bit of guidance, and permission to go figure it out.
Real expertise is built through:
👉 Getting the core information quickly and then applying it.
👉 Experiencing real problems and solving them.
👉 Making mistakes and refining your approach.
👉 Working alongside people who are already great at what you’re trying to do.
When to Credential — and More Importantly, When to Not
I have an M.S. degree from Boise State in Organizational Performance and Workplace Learning. I even published peer-reviewed academic research in the field.
By all traditional measures, I should be a textbook example of how formal education builds expertise. The truth is, though I did good work and earned good grades, I did it with minimal effort and even less actual learning. Not because I wasn’t engaged, but because the system was designed in a way that made it possible. I learned some things, sure, but very little of it had real-world utility. It didn’t prepare me for the complexity, pressure, and unpredictability of actually doing the work.
The most valuable thing I got from my education? The credential.
And to be fair, that credential mattered. The people who hired me at Charter Communications valued it—people who, by the way, were some of the founders of the Sales Enablement Society. It opened a door for me. It gave me credibility in the eyes of people who valued formalized learning.
But when I think about what actually made me competent in my career, it wasn’t classroom discussions or academic frameworks that led to a degree.
It was friction. It was pressure. It was the moments where the stakes were real, where failure actually meant something, where I had no choice but to figure it out.
Don’t get me wrong, credentialing has its place. In onboarding — in foundational training — it can ensure new hires understand the core building blocks of the business, and that makes sense.
But in highly iterative, fast-moving, frontier environments, static credentials often fail.
When things are constantly evolving, you can’t rely on a one-and-done certification model where people learn something once and assume they’re set for the quarter. You have to create a culture of constant curiosity, where learning isn’t about checking a box but about staying engaged, keeping up, and continuously adapting.
That’s how I really learn anyway. That’s how I develop a point of view and start to build expertise. Not through coursework and certification, though engaging with knowledge was helpful—but the real learning happens by navigating real challenges, making real decisions, and experimenting in the moments where it actually matter.
How to Actually Build Expertise in Your Organization
If you want an organization of experts, stop trying to train them into existence. Instead, build a system that naturally develops expertise:
✅ Hire for learning mindset, not just experience.
- Passion, curiosity, and adaptability matter more than anything — especially more than the resume and existing knowledge.
- The best hires are the ones who actively seek to understand the business, the customer, and the product—without needing it spoon-fed.
✅ Enablement isn’t a single department’s job—it’s everyone’s responsibility, especially managers.
- Frontline managers should be the primary force behind real learning.
- Great managers are great coaches. They guide, challenge, and push their teams toward growth—not through slides but through real deal reviews, problem-solving sessions, and tactical feedback.
✅ Ditch rigid training in favor of structured support.
- Training shouldn’t be opt-in, but it should be need-driven—focused on what actually matters in the moment rather than some artificial roadmap.
- Create spaces where people can raise real challenges and work through solutions with experts.
- Scale expertise by identifying who’s already great and amplifying their influence.
✅ Normalize failure and iteration.
- Expertise is built through cycles of trying, failing, adjusting, and trying again.
- Create an environment where people feel safe taking risks and learning by doing.
✅ Turn the firehose into a fountain.
- In a fast-moving org, you can’t “certify” people and expect them to be good for a quarter, let alone a year.
- Instead of overwhelming people with static training, create a culture where people naturally absorb, discuss, contribute, and refine their understanding over time.
Charlatans, Snake Oil, and Over-Engineered Bullshit
The biggest distractions from real learning come from those who try to package it into a product, a formula, or a promise that doesn’t hold up in the real world.
🚨 The Sales Training Snake Oil Merchant – The one who promises a guaranteed 58% improvement in productivity with their revolutionary 10-step system.
🚨 The Certification Industrial Complex – The endless cycle of badge-collecting, mandatory coursework, and bureaucratic hoop-jumping that creates the illusion of competence but doesn’t drive performance.
🚨 The “Data-Driven” Fantasy – The idea that every enablement initiative must be perfectly measurable, forecastable, and directly tied to X% improvement in Y metric. Some of the most important learning comes from things that aren’t neatly trackable.
🚨 The Checkbox Training Culture – The belief that if we just put people through enough training, they will automatically be successful. Training is not a magic wand.
Throwout Old Playbooks, Build Real Experts
If you want to turn your workforce into rigid process-followers—or if you’d like to be out of a job in two years (the average tenure of a sales enablement leader)—keep relying on traditional L&D models.
If you want dynamic, adaptive, deeply skilled experts, you need to burn the old playbook.
Real learning isn’t a rigid process—it’s a mindset, a way of working that thrives in the right environment. The best teams don’t wait to be trained; they dive in, figure things out, and learn by doing. And the best enablement teams don’t force people through structured learning journeys—they create the conditions for continuous growth by making information easily accessible, encouraging ownership, and fostering real-world application.
Real learning doesn't happen through certifications or compliance—it’s developed through iteration, experimentation, and a culture where learning is embedded in the work itself.
That’s how real expertise is built.