Why Your Best Sellers Should Lead Sales Training (Not Your Enablement Team)

Introduction

If you’ve ever watched a top rep sit through an enablement-led training, you’ve probably seen their skepticism. The look that says, “This sounds great in theory, but I’d like to see someone actually pull this off with a real stakeholder.”

Which begs the question: What if your enablement team’s biggest value isn’t in delivering training at all, but in orchestrating who delivers it?

In this article, we’ll break down why the most effective sales training doesn’t come from enablement, where it actually comes from, how to make training stick, overcome resistance, and more. 

The Credibility Gap: Why Sellers Don't Listen to Enablement

“Quite frankly, Ross, no one will care if I get in front of a sales team and tell them, ‘this is how you should do it,”’ stresses Andrew Zinger, the Senior Director of Global Sales Enablement at Fastly. 

Sellers need proof, not theories. They’re judged on whether they hit quota, not on how closely they follow a playbook. And because most enablement professionals don’t carry a quota, their advice can feel like an “experience disconnect.” 

Sellers want proof, not theories. They’re judged on whether they hit quota, not on how closely they follow a playbook. So even when enablement has the best intentions, if the guidance isn’t coming from someone who’s actively winning deals right now, most reps won’t change a thing. When they introduce a new talk track or methodology, sellers quietly think, “Okay . . . but would this actually work with the CIO I’m meeting tomorrow?”

Rather than chance it, sellers stick to what’s working. They live by the “show me” rule. They want to see another seller (someone in the trenches with a number on their back) run the play successfully before they adopt it themselves. If a top AE walks through how they cracked a Fortune 100 account, everyone leans in. If enablement walks through the same example, the room is polite, but skeptical because they’re not convinced the guidance comes from firsthand experience.

It’s even harder to get veteran sellers with a decade or more of experience on board. These people aren’t dismissive by nature, but they know almost instantly whether a suggestion is practical or not. And if enablement makes a suggestion based on little to no time in the field, and without understanding the real pain points or dynamics of the conversations sellers are having, those veterans mentally check out. They think, “If you haven’t lived this, you can’t teach me how to do it.”

The Peer Evangelization Model: How to Make Training Actually Stick

If credibility is the barrier to effective enablement, then peer evangelization is the key to make training stick. This model shifts training from “enablement teaching sellers” to “sellers teaching sellers,” with enablement quietly architecting the entire system behind the scenes.

Component 1: Strategic Identification

Not every top performer is the right person to teach others and not every high-revenue seller is using repeatable, teachable behaviors. 

Strategic identification boils down to choosing sellers who:

• Have unlocked deals in unique ways or consistently grow complex accounts
• Can explain how they win
• Are reliable closers with existing peer respect 

Think about the rep who consistently turns multi-threading skeptics into champions by mapping buying committees in ways the rest of the team hasn’t considered. Maybe they’ve spotted a pattern like bringing director-level operators into the conversation before finance, which helps move deals X percent faster.

That type of insight is teachable, specific, and directly tied to how deals actually get done.

Compare that to the rep who closed a massive six-figure renewal simply because the customer was already inclined to expand. They’re a top performer on paper, but the win isn’t repeatable. There’s nothing the rest of the team can adopt or emulate.

The right evangelists are the ones whose success can be systematized. They’re landing big deals in a way others can and want to replicate.

Component 2: Enablement as Orchestrator

Enablement teams have expertise in building frameworks, spotting patterns across deals, and turning scattered insights into clear, repeatable processes. They get this visibility through deal reviews, win/loss analysis, call recordings, CRM trends, and ongoing conversations with frontline managers and reps which gives them a broader view of what’s working across the entire sales org.

With that perspective, enablement can develop the core methodology and structure reps need. But rather than having enablement walk the team through those processes themselves, it’s far more effective for a top-performing rep to take the lead, because they bring the “in-the-trenches” credibility. When a seller who’s actively closing complex deals explains how they applied the framework, their peers listen. 

"We work with the best of the best within their teams to evangelize and spread that gospel. You're more than likely going to want to be like somebody who's successful and take one of their frameworks or approaches and make it work for you," says Andrew. 

Component 3: Crowdsourced Best Practices

Most sales meetings default to pipeline reviews where everyone reads out their deals, the manager gives feedback, and then everyone goes back to their corner. Nothing new is learned, nothing is shared, and nothing compounds.

But one of the most effective ways to turn individual wins into team-wide capability is to crowdsource best practices. You can do this by asking questions such as:

1. What win did you have this week, and what specifically made the difference?
2. Who overcame a tough objection or roadblock, and how did you do it?
3. Which upcoming call are you nervous about, and how can the team help pressure-test the approach?

Asking questions such as those outlined above helps surface best practices and create space for: 

• Sellers to walk through recent wins and highlight what actually moved the needle
• Deal debriefs where the group scopes alternatives or strengthens weak plays
• Practicing upcoming high-stakes calls as a team, not in isolation

Think about the difference between a manager saying, “Make sure you multithread,” and a peer saying, “Here’s the exact email I used to get the CFO into the deal and here’s why it worked.” One is instruction. The other is replication-ready insight.

How to Identify Which Sellers Should Lead Training (The Selection Criteria)

Choosing the right sellers to lead peer-driven training isn’t as simple as picking the top of the leaderboard. You’re looking for people whose success is both credible and teachable. 

In this section, we’ll walk you through how to identify which sellers should lead training. 

Criterion 1: Recent, Relevant Success

The best peer trainers aren’t just high performers, they’re also sellers who have wins worth replicating.

You want the rep who:

• Unlocked a stuck enterprise deal by reframing value for the CFO
• Expanded a small footprint into a multi-year, multi-product contract by pulling in an unexpected champion
• Turned a late-stage detractor into an advocate through creative stakeholder management

And the success needs to be recent. A brilliant play from two years ago doesn’t carry the same weight in a market where buying committees have tripled and procurement scrutiny has doubled. Reps trust what was proven last quarter, not last fiscal year.

Criterion 2: Ability to Articulate Methodology

Some people are great at selling, but not so great at teaching. They know how to work a room, navigate objections, or create urgency. But when you ask them to explain how they did it, they can’t. 

To test whether a top rep is able to articulate their methodology, ask them to walk you through the exact steps they took to win a recent deal. If their story is vague, nonlinear, or luck-based, they’re probably not ready to teach others. 

Another approach is the “shy away” test. Invite them to share their process in a meeting. If they struggle to articulate their takeaways or outline their steps, this shows you they’re a great seller, but not a great evangelist. 

Criterion 3: Peer Respect and Credibility

If this one sounds simple, that’s because it is. Without peer respect, even top reps will lack the credibility needed to influence how others sell.

Look for reps who are:

• Consistent quarter after quarter, not just riding one lucky deal
• Using repeatable processes that other sellers can adopt and apply
• The people teammates already lean on for help with calls, negotiations, or tricky deal dynamics

"I'm sure somebody on your team has unlocked a deal in a unique way, and you can crowdsource some of those best practices or learnings together in that environment," explains Andrew.

The Manager's Role: Making Space for Peer Learning (Not Just Pipeline Reviews)

You can identify the right evangelists, build great frameworks, and crowdsource best practices, but none of it matters if managers never give their teams the time to put it into motion.

The Problem with Pipeline-Only Team Meetings:

Most reps live in Salesforce or whatever CRM your team uses. They know the data. They’re familiar with the dashboards. And they know their quota and where they stand. That’s why pipeline-only meetings are inefficient and rarely groundbreaking.

Rather than working through real deal challenges, practicing conversations, or sharing what’s actually moving opportunities forward, reps spend their time reviewing the same updates everyone already saw in the CRM, which wastes time and drains one of the few moments the team has to learn from each other.

The "Practice Your Craft" Philosophy:

“Not every team meeting has to be a pipeline review. I think that's a missed opportunity. I think team selling is key... People rush home and practice piano or guitar or pickleball or like me trying to relive their youth by playing hockey. But rarely do we practice our craft. All those other things aren't paying the bills,” says Andrew. 

Everyone deserves time to unwind and practice the things they love — guitar, sports, art, whatever recharges them. But the reality is that reps rarely put the same intentional effort into the conversations that determine whether they hit quota.

Many sellers treat skill development as something that happens on the fly rather than something to be practiced. And that’s exactly where deals stall, slow down, or fall apart.

Use team meetings as an avenue to rehearse high-stakes deals in your reps’ pipelines so they can pressure-test their approach, refine their messaging, and walk into those conversations fully prepared instead of hoping it all comes together in the moment.

How to Structure Peer Learning Sessions:

Once you set aside regular time for your reps to practice their craft, the next step is structuring these sessions in a way that’s both meaningful and high-impact. 

Here are some suggestions for how to do that: 

• Role-play the biggest discovery call of the week as a team: Focus on your team’s biggest upcoming call, and walk through it together. Let the reps test different openers, value framing, and questions before they face the buyer.
• Have sellers share their approach to a common challenge: Whether it’s navigating procurement delays, re-engaging a quiet champion, or dealing with a skeptical CFO, let the rep who’s cracked it walk the team through their play.
• Practice objection handling or specific buyer personas: Run top objections and specific buyer personas. Examples include ROI pushback, timing, and budget constraints. 
• Debrief recent wins: Analyze recent wins and ask your team, “What worked and why?

Overcoming Resistance: The Two Outcomes When You Give Sellers the Stage

When you invite a rep to walk the team through how they win deals, one of two things usually happens: they either realize they don’t have much to share or they share insights others want to emulate. 

Outcome 1: They Realize They Don't Have Much to Share

When a seller struggles to articulate their process, it often signals that their recent success was driven more by timing, product fit, or luck than by repeatable methodology. And that’s not a bad thing — it’s a helpful starting point. 

This moment becomes:

• A humbling experience that often makes the rep more coachable
• An opportunity for them to learn from others who do have clear frameworks
• A signal to you that they may benefit from structured skill development
• A reality check that sharpens their self-awareness

If they can’t explain it, they can’t teach it and, more importantly, they may not be able to repeat it. 

Outcome 2: They Share Insights Others Want to Emulate

This is the ideal scenario. When a rep walks through a clear, repeatable approach that helped them win or advance a complex deal, the rest of the team leans in. They ask questions, compare notes, and start to see how they can run the same play in their own pipeline. That’s how a strong framework evolves from one person’s success into something the entire team can adopt and scale.

Actionable insights create: 

• Internal champions for your methodology
• A culture of continuous learning, grounded in what’s working
• Reduced resistance to future training because the ideas came from within, not from above
• Faster adoption of best practices across the team

The Veteran Seller Challenge:

“There are some folks that are just resistant or feel like they don't need to maybe learn anything new . . . the 25-year vet in enterprise sales is the toughest individual to convert,” - Andrew Zinger.

And most organizations have at least one of these seasoned sellers who’ve seen methodology, reorg, and enablement initiative. They’re successful, confident, and usually skeptical of anything that feels like “training.”

That’s why traditional enablement rarely resonates with this group. But peer-led learning does. They’re more open to hearing what’s working for another veteran or top performer — someone who understands the same market pressures, buyer personas, and deal dynamics they do. It bypasses ego and speaks directly to shared experience.

What Enablement Should Do (If Not Deliver Training)

If enablement isn’t the one delivering training, then what should they be doing? Their value shifts from being the presenter to being the architect that designs, coordinates, and amplifies the learning engine behind the scenes.

Role 1: Architect the Methodology

Enablement defines what “good” looks like and creates the clarity reps need to execute consistently.

To do this, enablement:

• Designs the discovery framework reps use across segments
• Identifies the steps of multithreading
• Creates the negotiation playbook based on win/loss patterns

In real-world application, this might look like enablement noticing that late-stage deals consistently stall when the CFO enters the process. After reviewing call recordings and win/loss notes, they build a “CFO Value Framework” that outlines the questions, data points, and proof needed to move that persona forward.

Then, instead of enablement teaching it, a top AE walks the team through how they used that exact framework to reopen a stalled enterprise deal, showing reps not just what to do, but how it works in the field.

Role 2: Identify and Coach the Messengers

Part of enablement’s role is identifying the sellers whose approaches are worth replicating and helping them translate their successes into something teachable.

To do this, enablement needs to:

• Choose reps who consistently excel at a specific part of the sales process
• Help those reps break down what they do, why they do it, and how they do it so it becomes a repeatable process others can follow
• Coach them on presenting their approach in a way that’s clear, structured, and easy for peers to adopt
  

For example, imagine a rep who’s exceptional at multithreading. Enablement will work with this rep to map out their steps, capture the messaging they use, and identify the signals that guide their next move. Then they’ll help turn that insight into a simple play the rest of the team can run with.

Role 3: Orchestrate the Program

Sellers take training seriously when it feels organized, intentional, and directly tied to the deals they’re working. That means orchestrating the program in a way that signals it’s worth their time. 

To do that, enablement must:

• Set a clear cadence for peer-led sessions so reps know when to expect them and can prepare meaningful examples or challenges
• Create consistency across teams and regions so every seller hears the same message, speaks the same language, and follows the same methodology
• Measure adoption by reviewing call patterns, CRM activity, and frontline manager feedback to see what behaviors are changing
• Iterate based on what reps use and ignore (because nothing erodes credibility faster than programs that don’t evolve with the field)

For example, let’s say enablement realizes only certain teams are regularly practicing objection handling, even though objections are derailing late-stage deals across the org. To fix this, they standardize a monthly “Live Fire” objection-handling session across all regions. Reps bring real objections from their pipeline, practice them in the group, and share the strongest responses. Within a quarter, adoption is visible in call reviews, and late-stage objection stalls decrease.

Role 4: Amplify What Works

When one rep uncovers a tactic that moves deals forward, enablement can amplify that success by turning it into a repeatable advantage for everyone.

To do this effectively, enablement focuses on:

• Documenting successful plays in a way that makes them easy to adopt and apply
• Turning high-performing messages or sequences into templates supported by context and usage guidelines
• Codifying emerging tactics into training materials so they become part of the team’s standard operating rhythm

For example, if a seller is able to consistently re-engage dormant champions using a specific outreach sequence, enablement would study the sequence, break down why it worked, add guidance on when to use it, turn it into a template, and roll it out across teams. 

“Trust me, this face does not need to be the frontline of every training that we do — that would not be great. The voices of our enablement are from the people that are doing that role today,” explains Andrew.

Key Takeaways: Implementing Peer-Led Sales Training

To successfully implement peer-led training sessions that will impact ROI, it’s important to:  

1. Acknowledge the credibility gap: Sellers are more likely to adopt approaches from peers who are winning today than from enablement professionals who aren’t carrying quota. Identify top performers with teachable methodologies, learn from them, and coach them on how to turn their approach into a clear, repeatable process.
2. Reposition enablement’s role: Enablement shouldn’t be the primary voice in training. Their value comes from architecting the methodology, selecting the right peer messengers, and orchestrating a program sellers trust and engage with.
3. Transform team meetings: Stop treating team meetings as pipeline reviews. Use them to build capability: share recent wins, practice upcoming high-stakes calls, and crowdsource solutions to real deal challenges.
4. Apply the “two outcomes” test: When sellers share their approach, one of two things happens: they surface insights worth scaling, or they reveal gaps that signal where to coach. Both outcomes improve performance.
5. Address veteran resistance intelligently: The enterprise rep who has “seen it all” rarely responds to traditional training. But they will listen to another veteran or top performer who’s succeeding under the same conditions. Peer-led learning is often the only way to reach them.