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Learning Principle #2: Learning Is a Journey

  • Writer: Mike Byrnes
    Mike Byrnes
  • May 21
  • 4 min read

Learning is a Journey
Learning is a Journey

Why Great Enablement Feels Like a Road Trip, Not a Race

Learning is a journey, not a pit stop


In enablement, we’re often asked, “How long will it take to train them?” — as if learning were a box to check on a project plan.

But we know better.

Learning isn’t a milestone to hit — it’s a rhythm to sustain.

Like any good road trip, it’s not just about getting from A to B. It’s about helping people navigate real conditions: uncertainty, unexpected detours, new terrain. And unlike a race, success isn’t about speed — it’s about staying on course and making meaningful progress.

The most effective enablement doesn’t try to shortcut the journey. It supports it — with the right tools, at the right time, in the right moments that matter.


The myth of mastery through exposure


One of the biggest misconceptions I’ve seen — especially in high-growth environments — is this: “If we told them once, we trained them.”

But exposure doesn’t equal retention. And retention doesn’t equal readiness.

Here’s what does build mastery:

  • Repeated practice spaced over time
  • Immediate feedback loops
  • Real-world application
  • Access to support at the exact moment of need

Timing and availability matter. We’re competing with Slack, CRM dashboards, customer demands, and time zones. If your best training resource is buried five clicks deep in your LMS, it might as well not exist.

That’s why enablement needs to move beyond content delivery and start thinking like a GPS — providing support when and where the learner actually needs it.

If your sellers can't access what they need in the moment — the talk track, the use case, the story — then we haven’t enabled them. We've just educated them.


The enablement road trip:

what the journey actually looks like


I think of the learning journey in four phases, each with a distinct purpose — and each building toward confident performance. Of course, timing is important and varies during the journey, and it's different everywhere. One example of an onboarding ramp program I ran that achieved an NPS of 64 is below.

  • Pre-boarding → Anchoring Expectations


Before day one, we don’t just send paperwork. We set tone. A quick team intro video. An interactive tour of the tech stack. A personal welcome from their future manager. We prime the path for connection, not just compliance.

  • Week 1-2 → Orientation, not Saturation


Instead of overwhelming them with product dumps, we set context. What’s our value to the market? Who do we serve? How do we win? When reps hear customer voices early, it gives purpose to the playbook.

  • Month 1-3 → Practice, Pressure-Testing, Coaching


Now they’re building muscle. We shift from learning about the role to practicing in the role — through call reviews, mock scenarios, peer feedback, and manager-led coaching. This is also where we scaffold field activity with increasing levels of complexity and real customer interactions.

  • Month 3-6 → Momentum and Integration


Reps are running, but they’re still growing. This is where too many programs fade — but it’s actually the perfect time to reinforce. We roll out advanced deal strategy sessions, peer mentoring, and reflection huddles — not just to refine skill, but to strengthen identity.


The journey in action: powerful, natural exploration


At one client, we noticed something interesting. By week two, reps could articulate our value prop — but they weren’t applying it fluidly in live discovery calls until month three or four. Knowledge wasn’t translating into confidence or performance.

So we reimagined the approach.

Instead of front-loading more training, we leaned into what the brain does best: explore.

John Medina, molecular biologist and author of Brain Rules: 12 Principles for Surviving and Thriving at Work, Home, and School, puts it this way:

"We are powerful and natural explorers."

Learning doesn’t stick when it’s passive. It sticks when it’s active, experimental, and emotionally engaging. So we built a three-stage “discovery road trip” that gave reps structured, real-world exploration — layered with increasing complexity and support.

  • Stage 1: Simulations and Safe Practice


Reps began with AI-driven mock calls to build confidence and muscle memory. At the same time, they shadowed discovery calls and rehearsed in low-stakes field interactions. This safe starting point gave them the space to test, observe, and ask.

  • Stage 2: Peer Huddles and Real Talk


We introduced objection-handling huddles and assigned reps active roles in actual customer conversations. They faced real friction, then debriefed it. Learning accelerated not just through content, but through tension, emotion, and reflection — all critical to memory formation.

  • Stage 3: Field Execution and Manager Coaching


By month three, reps were running full discovery calls. Managers joined live sessions and conducted structured debriefs. The loop closed: reps explored in the field, reflected with their coaches, and refined their approach with intent.

We didn’t just get smarter about what to teach — we got intentional about when and how to reinforce. And perhaps more importantly, we trusted our reps to explore, test, and learn on the job — not just in the classroom.

The result? A 40% increase in discovery-to-proposal conversion. But more importantly, reps weren’t just reciting messaging — they were owning it. Because we didn’t force knowledge into them — we designed a journey that invited them to discover it for themselves.


What to ask yourself when designing a journey


  • Are you planning for learning moments, or just scheduling training events?

  • Do your systems allow easy, in-the-moment access to content when it’s needed most?

  • Are you sequencing reinforcement in sync with reps’ actual field experience?

  • Do managers have clear roles and tools to coach within the journey?

In Closing: Your Role as a Journey Designer


The best enablement isn’t fast.
It’s purposeful.

You’re not just creating content — you’re designing a road trip. You anticipate the turns, support the detours, and celebrate the small wins along the way.

Because in sales, performance isn’t born in the first week. It’s built over time — through curiosity, courage, and the kind of exploration our brains are wired to crave.


 
 
 

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