From one-off sessions to scalable enablement programs

You know the drill: a new process rolls out, revenue stalls, or a leader asks for "just a quick session to fix it".

So you build a one-off training. Everyone nods, some ask questions, and a few weeks later... nothing's changed.

The truth? One-and-done doesn't get it done. And it's not your fault - it's the system 🤯

The problem with reactive enablement

Enablement isn't a presentation. It's not a Notion page. And it's definitely not a last-minute deck delivered over lunch.

Those can all be tactics. But without a program behind them, they rarely drive results. Why? Because:

  • Humans forget - fast. Most training is forgotten within days if it's not reinforced.

  • People learn differently. You need async, live, hands-on, and bite-sized formats.

  • New hires keep coming. So you'll end up repeating the same sessions over and over... unless you scale.

What scalable enablement actually looks like

Real enablement isn't about "delivering knowledge". It's about building competence and confidence - on repeat. That means:

  • A clear curriculum mapped to role, ramp, and revenue stages

  • Blended learning, combining async content with live sessions, shadowing, and practice

  • Reinforcement loops, not just one-and-done moments

  • Feedback and measurement, so you know what's landing (what's not)

  • Scalability, so new team members don't rely on tribal knowledge

Whether you call it a Sales Academy, CS Academy, or GTM Bootcamp, the name matters less than the structure behind it.

If it can't scale without you repeating yourself - it's not a program yet.

How to get started with your first program

Whether you're starting from scratch or formalizing what's already happening, here's a simple way to build your first program:

#1 Pick a focus

Start with one critical moment:

  • Onboarding for a new AE

  • Up-skilling for a CS team handling renewals

  • Tool adoption for a new CRM or sales methodology

Don't build everything. Pick the moment that moves the needle.

#2 Define success

What does "enabled" look like? Be specific.

  • Time to first meeting?

  • Win rate on a new product line?

  • Confidence score from a manager assessment?

If you can't measure it, you can't improve it.

#3 Map the journey

Lay out the experience:

  • What do people need to know, do, and use?

  • What format is best at each step? (Hint: not everything needs a live session)

  • Where does reinforcement happen? (Think: coaching, templates, peer learning)

#4 Build the minimum viable program

Start small:

  • A short video intro

  • A checklist or playbook

  • A team sync with scenarios or Q&A

  • Manager follow-up questions

You don't need a full LMS or 12-week course. You need clarity + consistency.

#5 Test and evolve

Pilot it with a cohort, gather feedback, and improve as you go. Programs should be living systems - not perfect the first time.

Don't forget your partners

If you're enabling partners (or plan to), the same principles apply. In fact, they're even more important - because you can't rely on hallway conversations and Slack threads to fill the gaps.

We'll go deeper into Partner Academies in a future edition.

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The anatomy of an enablement academy

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The enablement metrics that actually matter