Scaling without soul crushing: how teach-back, AI coaching and culture drive real sales performance

Shownotes

Sales teams today are overwhelmed with tools, dashboards and AI promises, yet execution in the field continues to break down. Traditional sales enablement focuses on completion, not capability, leaving reps underprepared, disengaged and burnt out.

In this episode of the OnBase podcast, Barry Flaherty and David Thomson explain why teach-back sales training is redefining modern sales enablement, and how AI coaching can accelerate performance without stripping away humanity. Drawing on decades of experience across enterprise sales, scale-ups and behavioural science, they share what actually works when it comes to onboarding, coaching and scaling sales teams.

If you lead sales, enablement or revenue teams and are questioning whether your training really translates into results, this conversation delivers practical, experience-led insight you can apply immediately.

Best Moments

• 03:05
  Why most sales training fails in practice
• 06:43
  Capability over completion explained
• 09:38
  AI as coach vs AI as cop
• 12:27
  Reducing ramp time and onboarding failure
• 18:19
  Why information alone never transforms performance
• 24:40
  Teach-back in real sales environments
• 31:30
  Scaling capability across teams
• 40:38
  Applying these ideas beyond sales

Why traditional sales training fails in modern revenue teams

Most sales training today is designed to be completed, not demonstrated. Reps watch videos, pass quizzes and tick boxes, but rarely prove they can apply what they’ve learned in real conversations.

Barry and David unpack why informational training alone fails, how this leads to long ramp times and high churn, and why capability must be visible, verifiable and repeatable across the organization.

How teach-back sales training builds real capability

Teach-back sales training flips the model. Instead of passively consuming content, reps are required to explain concepts in their own words and demonstrate understanding.

In this episode, you’ll learn how teach-back:

• improves knowledge retention and confidence
• exposes gaps early during onboarding
• shortens ramp time for new hires
• creates a shared sales language across teams
  

By focusing on demonstration rather than completion, leaders gain clarity on who is truly capable and where coaching is needed.

AI coaching for sales teams: coach vs cop

AI is becoming a permanent part of sales enablement, but not all AI adds value. Barry introduces a critical distinction: AI should act as a coach, not a cop.

When used correctly, AI coaching for sales teams:

• reinforces learning in real time
• provides feedback without policing behaviour
• reduces admin and cognitive load
• supports peer-to-peer coaching rather than replacing it
  

The conversation highlights why black-box AI that issues commands without context erodes trust and adoption, and how coaching-led AI strengthens execution instead.

Scaling sales teams without burnout or culture loss

Scaling revenue teams often comes at the expense of culture. This episode explores how teach-back methodologies and shared frameworks help teams scale without soul crushing.

Barry and David explain how:

• shared language improves collaboration and coaching
• culture is reinforced through peer learning
• onboarding becomes a signal, not a gamble
• confidence replaces compliance as teams mature
  

The result is stronger execution, lower churn and a healthier sales culture.

Key insights from this episode

• Capability matters more than training completion
• Teach-back sales training accelerates onboarding and retention
• AI coaching works best when it supports, not controls
• Culture scales through shared language and peer coaching
• Execution improves when learning is tied to real deals

Quotes

“AI should be a coach, not a cop.”

— Barry Flaherty

“You can’t get a transformational result from an informational product.”

— David Thomson

Resource recommendations

Books:

• Pre-Suasion by Dr. Robert Cialdini
• Ecosystem-Led Growth by Bob Moore

About the Guests

Barry Flaherty

Barry is a GTM and sales strategy Leader and Board advisor/member. He has 25 years of experience in Tech and Media that includes Enterprise Sales & Alliances in integration, cloud and automation. He is the Founder of All Good People and is now growing a portfolio of established Tech companies and scale up’s and capital raising.

Connect with Barry.

David Thomson

Founder and CEO of Suada, David is dedicated to helping organisations unlock the full potential of their people through cutting-edge digital learning solutions. With over 25 years of experience in sales, technology, and business transformation, he lead Suada’s global mission to revolutionise online learning by incorporating the science of retention and persuasion.

Connect with David.