Sales Leadership
Why Your Best Rep Might Be Your Worst Hire
J
John Cunningham
Founder, Revenue Factory
February 6, 2026
9 min read

You just hired a "natural."
They crushed the interview. Stories of monster deals. Presidents Club three years running. A Rolodex that could fund a quarter.
Six months later, you'll wonder why you celebrated.
## The Natural Seller Paradox
Here's the uncomfortable truth: your best closer might be your worst hire.
Not because they can't sell. They can. That's the problem.
Naturals succeed through instinct, relationship, and improvisation. They don't follow your methodology because they don't need to. They don't document their process because they don't have one. They close deals in ways that can't be taught, replicated, or scaled.
When they win, you can't learn why.
When they leave, you can't replace them.
When others watch, they can't copy.
You haven't hired a rep. You've hired a dependency.
## What Naturals Actually Do
Watch a natural seller work and you'll see something fascinating: nothing you can teach.
**They read rooms.** Not through a framework—through intuition honed over decades.
**They build rapport instantly.** Not with techniques—with genuine charisma you can't bottle.
**They know when to push.** Not from scripts—from pattern recognition they can't articulate.
**They always seem to know the right person.** Not from prospecting—from years of relationships.
This looks like mastery. It feels like magic. Managers love watching it.
But try to extract their method and you get nothing useful:
"I just feel when they're ready."
"You have to know when to go off-script."
"It's about building relationships."
These aren't strategies. They're post-hoc explanations for unconscious competence.
You can't train "feel." You can't scale "relationships." You can't hire for "just knows."
## The Metrics Mirage
Natural sellers look great in dashboards:
- Highest quota attainment ✓
- Largest average deal size ✓
- Best win rate ✓
- Most revenue ✓
What the dashboard doesn't show:
- **CRM discipline:** Sparse. Notes are minimal. Next steps are vague.
- **Methodology adherence:** Optional. They use what works "for them."
- **Forecasting accuracy:** Terrible. They trust gut over stages.
- **Knowledge transfer:** Zero. No one learns from their calls.
They're performing. They're not building.
## The Four Problems with Naturals
### 1. They Can't Teach What They Do
Ask a natural to explain their discovery process and watch them struggle.
They don't have a discovery process. They have conversations. The Pain Funnel? They never learned it. They instinctively ask good questions—but can't explain which questions, in what order, or why.
This matters when you need to scale. A team can't copy intuition. They need frameworks, steps, and scripts. Naturals can't provide these because they don't use them.
Your best performer becomes your worst coach.
### 2. They Won't Follow Your Process
You invested in Sandler. You trained the team. Everyone executes the methodology.
Except your natural. They have their "own approach."
At first, this seems fine. They're closing deals. Let them do their thing.
But two things happen:
**Other reps notice.** If the top performer doesn't follow the process, why should anyone?
**Management loses leverage.** You can't require methodology when your star ignores it.
One natural seller erodes the entire system. Not through malice—through exception.
### 3. They Create Hero Dependency
Look at your revenue distribution:
- Top performer: 35% of team revenue
- Next two reps: 25% each
- Remaining five reps: 15% total
This isn't a sales team. It's a hero with supporting cast.
When the hero has a bad quarter, you miss plan.
When the hero goes on vacation, pipeline stalls.
When the hero gets poached, you're in crisis.
Natural sellers don't build organizations. They prop them up.
### 4. They Leave
Naturals get recruited constantly. Bigger territory. Better comp. More interesting products.
And when they leave—and they will—what remains?
- A team that never learned from them
- A process they never followed
- A hole that can't be filled
- A dependency that never diversified
You're not back to zero. You're in the negative.
## The Coachable Rep Alternative
Here's the counterintuitive move: hire for coachability over capability.
A coachable rep with B+ talent will outperform an uncoachable A+ talent over time. Here's why:
**They follow the process.** Every time. Which means they improve systematically.
**They accept feedback.** Without defensiveness. Which means they develop faster.
**They document everything.** Because that's the standard. Which means others can learn.
**They're replicable.** What makes them successful can be taught. Scaled. Systematized.
**They stay longer.** They're not constantly recruited because they're not the flashy star. They're steady, reliable, and growing.
One coachable rep creates the playbook. Ten coachable reps become a predictable revenue engine.
## What Coachability Looks Like
In interviews, look for these signals:
**They credit systems.** "The methodology helped me identify that I was skipping budget." vs. "I just know when to ask about budget."
**They describe improvement.** "I used to struggle with objections until my manager showed me the reversing technique." vs. "I've always been good at handling objections."
**They ask for feedback.** Actively. Genuinely. Not defensively.
**They're curious about your process.** Instead of explaining why theirs is better.
**They have clear frameworks.** They can explain what they do, step by step, in a way someone else could follow.
On calls, coachable reps:
- Try new techniques when coached
- Ask clarifying questions
- Apply feedback to the next call (not the tenth)
- Credit the methodology when it works
Naturals resist this. They've succeeded without frameworks. Why start now?
## Building a Coachable Team
This isn't about avoiding talent. It's about defining talent correctly.
**The old definition:** "Can this person close deals?"
**The new definition:** "Can this person close deals in a way that teaches others to close deals?"
That second question changes who you hire, how you onboard, and what you reinforce.
You want reps who:
- Execute methodology consistently (not "when it feels right")
- Document their deals thoroughly (not "I know it, why write it")
- Share what works openly (not "that's my secret")
- Accept coaching gracefully (not "I've got it figured out")
These reps might not close the biggest deal in Q1. But by Q4, their approach is the template. By year two, they're training others. By year three, you have a system instead of a star.
## The Revenue Math
Let's compare two hiring strategies:
**Strategy A: Hire the natural**
- Year 1: $1.2M in bookings (hero performance)
- Year 2: $1.3M (slight improvement)
- Year 3: Natural leaves. Replacement ramps. $800K.
Total: $3.3M over 3 years
**Strategy B: Hire two coachable reps**
- Year 1: $700K + $700K = $1.4M (learning the system)
- Year 2: $900K + $900K = $1.8M (methodology mastery)
- Year 3: $1.1M + $1.1M = $2.2M (plus they're training new hires)
Total: $5.4M over 3 years
The natural looks better in month one. The system wins by month eighteen.
## The Hard Conversation
If you have naturals on your team, this isn't about firing them. It's about honest assessment:
- Are they following the methodology? If not, why is that acceptable?
- Are others learning from them? If not, what's their team contribution beyond personal revenue?
- What happens if they leave? Can you replace them?
- Are they coaching others? Or just performing?
Some naturals can adapt. Given clear expectations and accountability, they'll adopt the process. But many won't. Their identity is tied to their "unique approach."
You'll have to decide what matters more: this quarter's hero revenue or next year's predictable growth.
## The Bottom Line
Your best rep isn't your highest performer.
Your best rep is the one whose success can be systematized. Documented. Taught. Scaled.
That's not the natural seller closing deals through instinct and relationships.
That's the disciplined executor following methodology, logging everything, and making the whole team better.
The best hire isn't your best closer.
It's your most coachable rep.
Build on that, and you build something that lasts.
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Sales HiringSales LeadershipTeam BuildingCoachabilitySales Management
J
About John Cunningham
Founder, Revenue Factory
John Cunningham is the CEO of AI Advantage Solutions, helping sales teams execute their methodology with precision using AI-powered coaching.
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