What great reps do differently: lessons from thousands of AI Role plays

We’ve seen countless role plays where sales reps deliver confident, polished product walk-throughs, only to lose momentum the moment they’re asked about ROI. They explain what the product does, not why it matters. They share how the platform works, but not what it prevents, saves, or accelerates.

The truth is, feature fluency isn’t enough. It needs business framing. The best reps make the product feel like the answer to a measurable problem. They tie every feature to value, every benefit to a business case, every explanation to what’s at stake if the buyer does nothing.

That’s exactly what Scott, our AI sales coach, has been helping reps do, coaching hundreds of sessions to sharpen the link between product knowledge and business impact.

Consistency over brilliance

A single strong call doesn’t define mastery. It captures a moment in time, but it doesn’t guarantee repeatability.

In one of our customer cohorts, we saw several reps spike once (scoring 96 out of 100), only to dip sharply in the following sessions. Others climbed more gradually - 46, then 53, then 68, steadily improving call by call. They practiced with intention, often using the same persona six times in a row, focusing on one micro-skill at a time.

Guess who performed best in the real world? Not the one-hit wonders, but the consistent practitioners.

Consistency beats brilliance. It's about quality at-bats, deliberate focus, and steady improvement. Learning, like enablement, is an iterative process. Show up, repeat what works, discard what doesn’t, and refine.

Structure creates momentum

After reviewing thousands of AI role plays, one thing stood out: reps who follow a consistent discovery structure create more momentum, faster decisions, and cleaner handoffs.

The highest performers weren’t asking more questions, they were asking the right ones, in the right order.

Calls that followed a clear arc (pain → business impact → solution → next step) led to higher conversion and better follow-ups. Calls that skipped steps or jumped between topics left buyers disengaged.

In one role play, a rep asked, “What systems are you using today?” The buyer shared a pain point, but the rep never dug deeper. No follow-up about impact, no question about cost, and the conversation fizzled. The opportunity stayed surface-level.

Discovery needs to build a path from pain to value with clarity and control.

What AI is teaching us about sales mastery

When we analyzed hundreds of AI role plays across teams, some clear patterns emerged:

• Reps who follow a structured discovery framework (pain → impact → solution) see significantly higher close rates.

  
  

• The ability to quantify ROI and the cost of inaction is one of the strongest predictors of deal acceleration.

  
  

• Reps who use data-driven narratives to handle objections outperform peers in competitive deals.

  
  

• Calls that end with a clear, time-bound next step are far more likely to convert

  
  

AI allows us to see these patterns at scale, turning instinct into insight and coaching from guesswork into precision.

And when AI insights align with what managers have been seeing on the ground, it builds trust in both directions. Data validates intuition. Intuition sharpens data.

The competitive advantage of great questions

Most of the scorecards our customers use include criteria for probing questions, and for good reason. The best reps don’t just ask, they investigate.

Research backs this up: top-performing reps ask more questions per call. But it’s not just about how many questions, when and how matter a lot too.

The highest-scoring reps in our simulations tend to:

• Follow up when they hear a golden nugget (“How is that impacting your team’s daily workflow?”)

  
  

• Use question stacking to dig deeper (“What have you tried before?” → “What happened?” → “What’s the cost of doing nothing?”)

  
  

• Build trust early, then time their deeper questions strategically.

  
  

• Use the buyer’s own answers to frame the narrative of the call.

  
  

Asking great questions is a competitive advantage. It’s what transforms discovery from interrogation into insight.

How the best reps practice

Our most successful users share a few core habits that accelerate skill growth:

• Deliberate practice. Some reps complete 40+ simulations a week, warming up before real calls or honing a specific micro-skill.

  
  

• Reflection. They analyze what’s working and what isn’t: “I realized which customer types I’m great with and which ones I still struggle to approach. Now I’m practicing more with the latter.”

  
  

• Iteration. They tweak openers, refine messaging, and test variations until performance improves measurably.

  
  

• Social learning. Top performers often share their learnings, compete playfully, and hold each other accountable.

  
  

At its core, great selling is great learning and the reps who treat every conversation as a chance to learn are the ones who grow fastest.