Introduction
Here's a stat that should give any sales leader pause—62% of sales reps fail to meet quota. That number isn't just a reflection of rep performance; it's a mirror held up to onboarding, coaching, and enablement strategies. As Mark Roberge, former CRO at HubSpot, explains, the root often lies in undetected skill gaps. And as sales leadership legend John McMahon emphasizes, closing those gaps isn't just about metrics—it's about intimacy and great coaching.
This post explores the intersection of onboarding, coaching, and skill gap analysis. It's a deep dive into why so many reps fail—and how to set them up to succeed.
The Skill Gap Problem According to Mark Roberge
Mark Roberge is known for building HubSpot's revenue engine from the ground up. One of his standout insights from The Sales Acceleration Formula is that the most common reason reps fail is a mismatch between skills and expectations—what he refers to as a "skill gap analysis" failure.
Rather than assuming all reps start at the same baseline, Roberge advocates for systematically identifying where each rep stands on key competencies like objection handling, storytelling, or discovery questioning. Without this, onboarding turns into a one-size-fits-none approach.
"You can't coach what you don't measure. Skill gaps are invisible until performance data and structured observation bring them to light."
— Mark Roberge, The Sales Acceleration Formula
Step 1: Define the Core Skills for Success
Before you can assess skill gaps, you need to define what "great" looks like. Roberge recommends outlining role-specific competencies—like handling objections, storytelling, running a discovery call, or building urgency.
"Treat sales training like product development. Build it based on clearly defined requirements."
— Mark Roberge, The Sales Acceleration Formula
Each role—SDR, AE, AM—requires a unique blend of skills. The key is identifying them explicitly, so you can coach and measure accordingly.
Step 2: Create a Repeatable Assessment System
Roberge introduced structured evaluation rubrics to score reps on specific skill sets during onboarding and ongoing training. These scorecards act like early detection systems, flagging skill deficiencies before they result in lost revenue.
With tools like Itero's customizable scorecard templates and automatic call scoring, sales teams can automate this process—turning subjective opinions into consistent, data-backed evaluations.
Step 3: Personalize Coaching and Training
Rather than generic onboarding for everyone, Roberge's method enables targeted development plans based on each rep's profile. For example:
- If a rep is strong in product knowledge but weak in objection handling, they might spend more time in AI-powered role plays with difficult buyer personas.
- Another rep might need to refine their discovery call structure, supported by Itero's simulated call feedback and persona-specific practice scenarios.
This kind of skill-specific onboarding accelerates time to productivity and boosts long-term confidence.
Step 4: Coach with Intimacy — Empowered by Skill Visibility
Once you've identified the skill gaps and personalized your training, the next—and arguably most critical—step is how you coach.
This is where John McMahon's coaching philosophy becomes your north star. In The Qualified Sales Leader, McMahon makes a bold but essential point: great sales coaching is rooted in intimacy.
"Coaching without connection isn't coaching—it's managing. And no one gets better from being managed."
— John McMahon, The Qualified Sales Leader
McMahon isn't talking about surface-level check-ins. He's referring to deep, trust-based relationships where reps feel understood, supported, and invested in.
And here's the connection many miss: Skill visibility creates the foundation for that intimacy.
Why Knowing Skills = Knowing the Rep
When a coach has a clear view into a rep's strengths and gaps, every conversation becomes more relevant, more compassionate, and more effective.
You can offer specific, supportive guidance:
"I noticed you're struggling to control the flow during discovery. Let's role play a few ways to bring the conversation back when a prospect goes off track."
This level of detail tells the rep:
- "I see you."
- "I'm not judging you—I'm here to help."
- "We're in this together."
Coaching With Empathy, Not Guesswork
This kind of intimacy-driven coaching does more than boost performance. It fosters:
- Psychological safety: Reps are more open about their struggles.
- Ownership: Reps take pride in their development journey.
- Connection: Manager-rep relationships deepen, leading to stronger team culture.
It's not just coaching. It's leadership.
Bringing It All Together: A New Model for Sales Enablement
Let's recap the four steps that reframe onboarding and coaching from a task into a competitive advantage:
- Define Core Sales Skills
Start with clarity. Identify the specific competencies reps need to succeed in your environment. - Assess Skills Objectively
Use repeatable rubrics, call scoring, and simulation data to map each rep's strengths and gaps. - Personalize Coaching and Training
Tailor onboarding and development plans to practice and focus on the areas that matter most for each rep. - Coach with Intimacy
Use skill insights to deliver high-empathy, high-impact coaching that builds trust—and performance.
Ready to Empower Your Reps from Day One?
The future of sales performance isn't about working harder—it's about enabling smarter, more connected coaching. With Itero, you can finally close the gap between training and trust, and turn every new rep into your next top performer.
