Redefining Enablement with Predictive Coaching, Measurable Proficiency, and AI That Actually Works

The latest episode of The Sales Readiness Podcast features a high-energy conversation between Ray Makela, Managing Director of Talent Development and Christina Brady, CEO and co-founder of Luster. With nearly two decades of GTM leadership experience, Christina brings a rare mix of sharp operator perspective and deep enablement expertise to the discussion.

In this conversation, she shares what’s broken with traditional enablement and how leaders can move from reactive to proactive without overwhelming their teams.

Here are five tactical lessons enablement leaders can take from the conversation:

1. Stop Practicing New Skills on Customers 

One of the most expensive ways to uncover performance gaps is waiting until a rep fumbles a live customer call. Christina urges teams to move away from this reactive approach and instead invest in ways to identify and address gaps before they show up in the field.

She recommends building role-specific practice and certification opportunities into your training cycle, especially before big product launches or territory changes. Instead of waiting for a bad call to surface a problem, encourage your sales managers to engage in regular 1:1 coaching conversations to identify areas for improvement early. As Ray points out, AI-based simulations are a great way to practice new skills in a risk-free environment.

2. Prescribe Specific Training, Don't Over Generalize 

Enablement teams often default to providing everyone with the same training program because they lack visibility into individual proficiency. Blanket training on a one-off basis often misses the mark and lacks the reinforcement sellers need to make meaningful behavior change. Christina emphasizes the importance of ongoing prescription-based training, giving each person what they need, when they need it, based on measurable gaps.

To do so, introduce a way to assess skill gaps upfront through simulations or manager assessments and let that help to inform the learning path. Providing ongoing training as opposed to discrete group sessions will close skill gaps.

3. Redefine What 'Ready' Means

Traditional onboarding often assumes that time equals preparedness. But as Christina points out, reps don’t suddenly become client-ready just because they’ve completed 30 or 60 days of onboarding. Readiness needs to be tied to demonstrated proficiency, not time served.

It’s essential to establish clear definitions of proficiency for foundational skills and assess them before reps engage with prospects. Ray notes it’s often better to delay call readiness than to lose pipeline due to unprepared reps.

4. Prove Enablement as a Revenue Driver 

Enablement is often treated as a cost center because its outcomes feel hard to measure. Christina challenges that mindset, arguing that enablement should be directly tied to revenue outcomes like ramp time, win rate, ACV, and efficiency. Top-performing enablement teams measure both leading and lagging indicators to tell the full story of enablement’s impact.

If you haven’t already, Christina suggests A/B testing your enablement programs. Run pilots, track metrics like pipeline creation and close rate, and compare against a control group. This is one way to build internal credibility and secure future investment.

5. Meet Reps Where They Are

One of the most overlooked barriers to enablement adoption is friction that disrupts their workflow. When reps are forced to log into separate systems to complete training, even the best programs fall flat. Christina advocates for in-the-flow-of-work delivery through Slack, calendar invites, LMS embeds, and mobile-friendly access.

It’s important to map your reps’ daily flow and embed key learning moments in their routine workflow.  For example, short simulations scheduled on their calendar before key calls, or quick refreshers linked from your CRM or CMS. Ray also recommends avoiding disruption with any tech investments to encourage adoption.  

Final Thoughts 

Enablement professionals are being asked to do more than ever, deliver results, prove impact, and support increasingly complex GTM motions. The conversation with Christina Brady is a reminder that the path forward doesn’t require more content or longer trainings. It requires precision, personalization, and a clear connection to performance.

Watch the full episode, Predicting and Preventing Revenue Impacting Mistakes.