Why do most enablement programs inspire but fail to transform?

In 100+ conversations with sales and customer success leaders, one theme keeps surfacing:

How we deliver coaching determines whether it compounds or disappears.

Every team I talk to invests heavily in enablement. Playbooks get written, SKO decks get built, workshops get booked. The intent is always right. But too often, that energy peaks in a single day and fades within a week. The reps leave inspired, but not transformed. The reason for this is that information alone doesn't change behaviour. You need reinforcement loops.

The best teams are realizing that coaching isn’t a calendar event. It’s a system. And like any system, it’s only as strong as its feedback loops.

Imagine a world where coaching is personalized to each rep’s real gaps. It's grounded in their actual calls, not hypothetical ones. Where feedback shows up just in time, and not as a post-mortem. It's a nudge while the lesson still matters. Where micro learning moments build on one another. They're stacking, compounding, turning insight into instinct.

It’s not about running more workshops or cramming more content into onboarding. It’s about designing a reinforcement loop that compounds over time; one rep, one behaviour, one moment at a time.

Because when coaching compounds, performance doesn’t just improve; it accelerates. And the teams that figure that out will separate themselves fast.

— Cliff