Podcast Summary

Podcast: Outside Sales Talk
Host: Steve Benson
Guest: Stephen Rhyne (CEO, conveyor.com)
Episode: Increasing Training Engagement with Your Sales Reps
Date: October 8, 2025

Episode Overview

This episode explores how companies can dramatically improve engagement in sales training. Stephen Rhyne leverages his 22 years of experience in recruiting, onboarding, and retaining outside sales reps to share insights into what works—and what doesn’t—when it comes to training today’s diverse and often distracted workforce. He covers strategies for making training relevant, interactive, and sticky, providing actionable advice for sales leaders who want to build motivated, high-performing teams.

Key Discussion Points & Insights

1. The Core Challenges of Training Engagement

• Changing Expectations (01:50): Stephen notes generational shifts in both employee loyalty and attention. Reps no longer expect to spend decades at a company, so you can’t take their engagement for granted.

• SELL the Training, Don’t Just Assign It (01:50):

  • Training must answer "what's in it for me?" for every rep. It should not just focus on company objectives but on pain points and personal benefits.
  • “Paint them a picture of the pain that’s going to be caused for you if you don’t understand this.” — Stephen Rhyne [02:53]

• Explain the Process & Set Expectations (04:40):

  • Orient trainees with an overview, like showing the full map in a video game, so they understand the journey versus dropping them straight into “level 1” with no context.

2. Making Training Engaging and Relevant

• Relatability Over Dry Content (05:38):

  • Both Stephen and Steve recall old-fashioned, passive learning (e.g., marathon VHS tape sessions). Those are not feasible for today’s workforce, especially “the TikTok generation.”
  • “I do not think you could get someone in the TikTok generation to do what they made us do.” — Steve Benson [05:38]

• Positioning and Intrigue (07:37):

  • Reps are often recruited and even pitched by other companies mid-training—your training needs to keep them excited and motivated.

3. Tactical Approaches for Better Engagement

• Chunking and Pacing (09:19):

  • Break content into smaller, digestible units (7-15 minutes each).
  • Incorporate quizzes and interactive elements—create “LEGO bricks” of knowledge rather than overwhelming blocks.

• Personalizing Learning Paths (12:07):

  • Avoid “lowest common denominator” training, which bores veterans and confuses novices.
  • Begin with diagnostic quizzes (hard and soft questions) to identify existing knowledge, then route learners to “brush up” or advanced material as needed.
  • This builds “learner trust”—reps see training as worthwhile rather than time-wasting.

• Learning Styles & Diversity (12:07):

  • Use a mix of media: video, audio, quizzes.
  • Focus less on supposed “learning styles” (auditory/visual) and more on maintaining relevance and trust.

4. Interactive & Creative Techniques

• Gamification (16:06, 22:37):

  • Implement leaderboards, challenges, rewards.
  • Publicly celebrate top performers to foster competition and community.
  • “Competition is not just for entry level … people love it at all ranks.” — Stephen Rhyne [24:34]

• Social Proof & SMEs (16:06):

  • Feature internal subject matter experts (SMEs) to demonstrate best practices, not just top execs or hired trainers.
  • Real stories from peers are more convincing and relatable.

• Belief-Building Campaigns (17:30):

  • Sometimes training isn’t the answer—prospective reps need belief that they can succeed. Early, peer-led video messages can reduce day-2/3 attrition by normalizing early challenges.

5. Role and Timing of Feedback

• Real-Time Feedback (25:39):
  • Mix feedback opportunities directly into lessons, not isolated post-training surveys.
  • Use instant polls and confidence checks at key moments.
  • Automated systems can trigger individualized follow-ups immediately, e.g., “Was this enough for you? If not, here’s more.”

6. Training Retention & Ongoing Success

• Focus on the Long Tail (28:11):

  • Follow up consistently after initial training; ongoing reminders and drip quizzes are more effective than one-time events.
  • “So many companies ... spend a bunch of money to make some crazy course ... and then they don’t do any follow up.” — Stephen Rhyne [29:20]

• Referenceability & Microlearning (32:20):

  • Modular micro-lessons are more shareable and referenceable for managers.
  • Bite-size content enables managers to reinforce learning quickly.

7. Measuring and Optimizing Training

• Meaningful Metrics (35:04):

  • Monitor more than completion rates: engagement funnels (where people drop off), quiz scores, qualitative video submissions, and tie training back to field KPIs wherever possible.
  • “It means nothing if you don’t do anything with it.” — Stephen Rhyne on gamification & recognition [23:58]

• Align Training with Business Goals (56:28):

  • Don’t check boxes—work backwards from concrete company objectives.
  • Test for real knowledge gaps; tease out training, collect reactions, iterate based on measurable impact.

Memorable Quotes & Moments

• “Nowadays, generations don’t like picking up the phone ... they want to know all the information first before they jump in.” — Stephen Rhyne [02:40]
• “You have to get good at the hook … start with what they get, then unfurl.” — Stephen Rhyne [40:42]
• “Treat your salespeople totally different than you would your own prospects and customers ... apply what you do with your customers to your reps.” — Stephen Rhyne [43:03]
• “The fight for attention is killing the ability to create a bigger knowledge graph earlier before you even need it.” — Stephen Rhyne [52:16]
• “Don’t just make training for the sake of it. ... Start with what goals do we have as a business?” — Stephen Rhyne [56:28]

Practical Takeaways

• Sell your training: Always lead with “why this matters for you.”
• Map the journey: Show reps the big picture before launching into content.
• Chunk & pace: Short, interactive bursts are king.
• Personalize: Use quizzes to adapt content to experience levels.
• Engage with games & competition: Early gamification helps identify future high performers.
• Feature peers: Champion real, relatable SME voices.
• Responsive feedback: Build in real-time surveys and poll moments.
• Ongoing reminders: Drip follow-ups and micro-quizzing retain learning.
• Measure what matters: Track engagement, not just completion, and align with business outcomes.

Suggested Resources

Learn more or connect with Stephen Rhyne:
conveyor.com – check out the "Get Pricing and Demo" option for guides and deeper insights.