Coaching Underperforming Sales Reps: How to Know When to Coach and When to Cut

Coaching underperforming sales reps is effective when it aligns with their inherent competitive wiring and motivation. Otherwise, it's sometimes better to cut your losses and focus on finding the righ...

Most sales coaching misses the mark because it's all about telling reps what to do differently. The real art of coaching is understanding their competitive wiring and building on what's already there.

By Kayvon Kay | Revenue Architect, Founder of SalesFit.ai

Understanding Underperformance: Data and Insights

Common Causes of Sales Underperformance

Underperformance in sales teams is a widespread issue that I've encountered often in my two decades of building 101 teams. Many managers turn to quick fixes. But the truth is, most underperformance requires deeper analysis. It's rarely about a lack of hustle or motivation. Often, it's about a mismatch in role alignment or insufficient skills development.

Based on my experience, common causes include:

• Mismatched roles: Reps are in positions that don't suit their strengths.
• Lack of clear process: Without a structured process, even the best reps flounder.
• Insufficient training: Ongoing development is critical for keeping reps sharp.
• Lack of competitive wiring: Not all reps are naturally wired to compete and win.

I emphasize starting with the right hire. Misaligned competitive wiring, as I've learned, leads to frustration and missed targets. Hiring with a focus on drive, coachability, and resilience—the 3 Pillars of Performance Wiring—can make a monumental difference.

Key Metrics to Track When Assessing Reps

Understanding why a rep is underperforming involves tracking the right metrics. I always recommend keeping an eye on:

1. Quota Attainment: The most direct measure of sales success.
2. Conversion Rates: It shows how well a rep turns prospects into buyers.
3. Sales Cycle Length: A shorter cycle generally means greater efficiency.
4. Pipeline Health: Ensuring there's a balance of opportunities at each stage.
5. Customer Retention: It reveals long term value creation abilities.

These metrics not only provide a snapshot of performance but guide tailored coaching efforts. Personalized KPIs help reps focus on precisely what to improve.

SalesFit Assessment vs. Traditional Evaluations

I've seen countless traditional evaluations miss the mark. They often focus on personality types or surface-level traits. Our SalesFit assessment, however, dives deeper into the core traits essential for sales success.

With my approach to the SalesFit assessment, I've made sure that every insight is immediate and actionable. This isn't just about identifying weaknesses—it's about capitalizing on natural strengths. By aligning reps' competitive wiring with their roles, you're setting them up for success. This thoughtful alignment is where effective coaching really begins.

As statistics from the Harvard Business Review suggest, the best salespeople aren't just hired—they're developed with precision, starting from the core traits that predict success.

The Power of Competitive Wiring in Sales Coaching

Why Personality Tests Won't Work

When it comes to coaching underperforming sales reps, reliance on personality tests is a misguided approach. From building 101 sales teams, I've learned that these tests often fail to capture the nuances of a sales rep's true selling potential. They focus on traits that might matter in a boardroom but fall short on the sales floor. What we need to understand is their competitive wiring — that inherent drive to win.

Consider this: two reps might both score high on "extroversion," yet one consistently closes deals while the other struggles. The difference isn't in their personality, as many might assume, but in their wiring for competition. Personality tests can’t reveal this.

Harnessing the Competitive Nature of Sales Reps

The secret sauce in effective sales coaching is understanding and harnessing a rep's competitive nature. This isn’t about telling reps what to change; it’s about leveraging what’s inherently there. My experience has shown that when you align a rep’s competitive wiring with their sales strategy, performance takes a remarkable turn.

In the context of real world sales environments:

• Reps showing strong drive push harder against quotas.
• Those with high resilience bounce back quickly from rejection and losses.
• Coachability translates into faster learning curves and adaptability.

In essence, a successful sales coaching strategy starts with assessing and understanding these competitive traits, not just listing personality types. Applying this nuanced approach has been key in the success stories from my work with diverse sales teams over my two-decade career.

Case Study: Transforming a Faltering CS into a Top Performer

A few years ago, I worked with a tech startup where the sales team was under pressure with missed quotas across the board. Among them was a Conversion Specialist named Sarah. She had energy and passion during meetings but struggled to close deals. After conducting a SalesFit assessment, her profile revealed incredible resilience and coachability — two pillars of the three performance wiring traits that reveal future potential.

With these insights, my coaching focused on harnessing her resilience to handle the high rejection rates in her role. I paired her with a nurturing but challenging manager with high Drive traits. He knew how to push and support her, providing both structure and motivation.

Within six months, Sarah transformed into a top performer, driving significant revenue growth for her team. Her monthly close rates increased by 35%. What made the difference wasn’t a change in her personality but a shift in recognizing and using her competitive wiring effectively.

This transformation story underscores the power of starting with the right insights. As SHRM points out, the cost of a bad hire can be astronomical, so understanding wiring isn't just a benefit—it's a necessity for sustainable team success (source).

In the end, real coaching doesn’t come from a script. It begins with accurate data and deep understanding — not hope.

The 3 Pillars of Performance Wiring: A Deep Dive

Coachability: Are They Open to Learning?

From my two decades in sales, I’ve learned that coachability is more than a nice-to-have trait. It’s foundational. Every top performer I’ve seen was open to feedback, willing to adapt, and eager to learn. I've watched teams transform when given data driven insights into their potential. Consider a software company I consulted for, struggling with stagnant growth despite promising products. Their team was set in their ways, resistant to new strategies. After introducing the SalesFit assessment, which pinpointed gaps in their approach, we identified two reps with high coachability scores.

These reps, initially middle-of-the-pack, surged ahead. All because they embraced our coaching on switching tactics and refining their pitch strategies. Within a year, their contributions resulted in a 20% bump in company revenue. The difference? They listened and took actionable steps. Coachability, as I’ve seen, can be the deciding factor between mediocrity and mastery.

Drive: The Motor Behind Quota Mastery

When building 101 sales teams, I've witnessed firsthand that drive is the engine powering any successful sales rep. It manifests in the relentless pursuit of quotas, the refusal to settle, and the hunger for growth. Drive doesn’t just mean being busy; it means being effective. A sales manager can’t afford reps who are complacent. During one of my earlier projects with a telecommunications firm, I observed that their top performer wasn’t the most experienced but had a raw, untamed drive to succeed. He constantly chased leads and turned objections into opportunities.

This rep, assessed with our platform, scored exceptionally high in drive, making him a prime example of quota mastery. His efforts led to securing a major client, adding $3 million in revenue within six months. Drive was his differentiator, proving that when correctly channeled, it can elevate a rep’s performance beyond expectations.

Resilience: Bouncing Back from the Brink

In sales, setbacks are inevitable. Resilience is the armor that sees you through tough quarters and missed quotas. Most sales coaching focuses on the immediate fix, but resilience asks: can a rep bounce back smarter? With SalesFit, resilience is a key metric. It’s not about personality; it’s about the ability to recover. I still recall a financial services firm where resilience became the cornerstone of revival. Their team faced a rocky start to the year, losing major accounts due to market shifts.

• They underwent targeted coaching, focusing on strategy adaptations.
• Resilient reps learned from the failures and rapidly applied insights.
• Within months, they recovered previous losses and added new clients.

This resulted in regaining $5 million in lost revenue, a testament to resilience being not just about survival, but thriving post adversity. Understanding and fostering resilience transformed setbacks into stepping stones, further underscoring its place in the 3 Pillars of Performance Wiring.

My experience shows, when integrated effectively, coachability, drive, and resilience are not just traits. They’re predictive indicators of a sales rep’s potential, forming the backbone of successful sales teams.

For more insights on the impact of resilience, I recommend reading this article from HBR.

Crafting the Right Sales Coaching Plan

Identifying and Building on Strengths

In my experience building 101 sales teams, I've seen that the best coaching plans start by recognizing each rep's unique strengths. Understanding competitive wiring is critical. Every great rep has that one thing they do remarkably well. It's about identifying it and then growing out from there.

Take, for instance, a software company I once worked with. Their sales team was around 25 reps, mostly struggling to hit quota. When I ran the SalesFit assessment, I noticed one rep scored exceptionally high in resilience but lacked in strategic skills. Instead of focusing on his weaknesses, we honed his resilience, pairing him with a mentor to develop strategic thinking organically. He went from middle-of-the-pack to leading the team by monthly close rates within six months.

Identifying strengths isn't just about boosting confidence. It lays the groundwork for a realistic plan that the reps can actually implement, increasing the likelihood of success.

Structuring Feedback for Maximum Impact

Feedback is often mishandled. Too vague, too brutal, too rare—it loses impact. When I coach, feedback is structured and timely. After identifying strengths, I use them as a lens for feedback. If a pipeline developer thrives in lead generation but falters in negotiation, focus feedback on how their existing skills in prospecting can adapt to negotiation scenarios.

• Be specific: Pinpoint exact actions or behaviors that need attention.
• Frequency matters: Regular check-ins—weekly or bi-weekly—ensure feedback is fresh.
• Encourage dialogue: Allow reps to voice thoughts, turning feedback into a conversation.

When I applied this to a retail company's team of 15 reps, initially 5 were underperforming. Within three months of structured feedback and clear expectations, four had improved performance by at least 20% each month. Structured feedback is not a one-size-fits-all; it requires adaptation and awareness of each rep's strengths.

Setting Realistic and Motivational Goals

Setting goals tied to strengths is another secret. I once worked with a manufacturing sales team of ten, and their goals were outdated, not reflecting individual potential. By revising goals to focus on each rep's competitive wiring, the reps were more motivated and their performance showed it. One rep's strength was in depth product knowledge but not cold-calling. So, we set goals around product demos and knowledge sharing, upping engagement and closing rates in key accounts.

According to HBR, tying goals to personal strengths fosters intrinsic motivation, a critical element for driving performance.

When goals are both realistic and motivational, they align rep efforts with company objectives seamlessly. It's the culmination of understanding strengths, delivering feedback effectively, and driving sales reps toward attainable achievements. This personalized approach ensures that coaching underperforming sales reps turns potential into measurable progress rather than turnover.

Revenue Architecture Model: Aligning People, Process, and Technology

Building the Foundation: Hiring Right

When I talk about sales being an architecture, the foundation I see is without question the people you hire. Over two decades, working with 101 sales teams, I learned that hiring right is about understanding competitive wiring. Each team demands a unique mix of Pipeline Developers, Conversion Specialists, Solutions Architects, and Enterprise Strategists. Hiring the wrong archetype can be catastrophic — costing companies up to $150K per bad hire, as SHRM highlights (SHRM: The Cost of a Bad Hire Can Be Astronomical).

Real story time: I worked with a mid-sized tech company struggling with quota attainment. Their team had eleven reps, but only three were hitting targets consistently. After conducting a SalesFit assessment, we discovered a mismatch in roles; they had too many Conversion Specialists and not enough Pipeline Developers. After realigning their team structure and making strategic hires, their revenue climbed by 30% over the next two quarters. This wasn’t magic. It was about aligning competitive wiring with role requirements.

Creating a Robust Sales Process

With the right people in place, you need a solid process. I’ve seen too many teams stumble, relying solely on charisma or individual quick wins. Early in my career, I learned the power of a defined sales process while helping a SaaS company with a 25-member sales team. They had no consistency. Every rep had their own way of doing things. By standardizing a process that emphasized key milestones and pipeline stages, their close rate improved by 20% within the first year.

A robust sales process should include:

• Clear stages from lead generation to closing
• Standardized communication templates
• A feedback loop for continuous improvement

Aligning people with process removes bottlenecks and establishes a rhythm, setting reps up for success.

Leveraging Technology Wisely

Most businesses start at the top with technology — the proverbial roof — wondering why the structure collapses. Tech is crucial, but it's an enabler, not a fix. I’ve seen teams throw money at the latest CRM or sales enablement tool, expecting it to fix foundational issues. It never does.

Take my experience with a high growth e-commerce firm. They were burning through cash on tech without understanding how it supported their sales architecture. We took a step back, focusing on aligning their CRM with actual sales activities and performance metrics. By the end of six months, their sales efficiency increased by 40%, all because the technology was aligned properly.

The key is wise use — do your reps know how to use the tech effectively? Is the data being used to drive decisions? Technology should augment your team's efforts, freeing them to focus on selling rather than being bogged down by tools.

The Revenue Architecture Model isn’t a buzzword. It’s a blueprint I've seen time and again drive significant improvements. When you align your hiring, process, and technology, you're setting up your sales team for inevitable success. In my experience, when you get this alignment right, underperformance becomes the exception, not the rule.

Real World Application: Stories from the Field

Success Story: Turnaround of a Struggling SA

Lessons Learned from Letting Go

When Technology Transforms Selling

When to Coach and When to Cut: Making the Tough Call

Signs a Rep Can Be Coached

I've been in the sales trenches for over two decades, building 101 sales teams and generating over $500 million in client revenue. From this, I know a struggling sales rep doesn't always need the door shown to them. There are signs that a rep can be coached. One such indicator is their coachability—a critical component of the 3 Pillars of Performance Wiring. Are they receptive to feedback? This trait often predicts whether coaching will bear fruit.

In a mid-sized B2B tech firm I worked with, we had a rep named Sarah. She was missing quota but showed signs of resilience and drive. Her willingness to adapt feedback into her selling process signaled potential. After her SalesFit assessment revealed high scores in coachability, we restructured our approach. With targeted coaching, acknowledging her competitive wiring, Sarah turned her numbers around within a quarter, eventually leading the team in closed deals.

Coachable reps often exhibit:

• Proactive engagement in coaching sessions
• Implementation of learned strategies
• Openness to adapting sales methods

Time and again, I've seen how these traits can transform a struggling rep into a top performer.

Indicators It Might Be Time to Part Ways

However, there are times when coaching is not the answer. I learned this the hard way early in my career. In one instance, a rep at a large enterprise was consistently missing quota. His SalesFit assessment showed low scores across the board, especially in resilience and drive. Despite exhaustive coaching efforts, his performance didn't budge.

These were the red flags:

1. Lack of improvement despite consistent coaching: No matter how much we adjusted the techniques, results were stagnant.
2. Resistance to feedback: Criticism was met with defensiveness rather than receptiveness.
3. Absence of drive: Demonstrated no personal initiative to enhance their sales skills.

We decided to part ways. It was a tough decision, but ultimately necessary for the health of the team and company. Statistics show that the cost of a bad hire can be astronomical (as much as $150,000), so sometimes, cutting losses is the most strategic move. SHRM provides an insightful perspective on this.

Balancing Empathy with Business Needs

Deciding whether to continue coaching or to cut a rep involves balancing empathy with business needs. This isn't just about the bottom line—it's about sending the right message to your team. They need to see empathy as well as decisive leadership.

I've always advocated for a smart yet empathetic approach. Analyzing competitive wiring through our 85 question SalesFit assessment helps provide clarity. It's not about what the rep can't do—it's about understanding where they might excel and if there's a pathway to success.

In another case, with a retail company of 30 salespersons, we faced a similar decision. One rep showed high potential in the SalesFit assessment but lagged in key metrics. Through personalized coaching and by adjusting their role to better align with their strengths, they eventually increased their sales by 30%. The lesson? Sometimes, wisely balancing empathy with clear business needs can revive a career.

Making the tough call requires data, introspection, and sometimes a leap of faith. But with the right tools, like a solid Sales Team Intelligence Platform, you can make informed decisions that benefit both the individual and the organization.

Future-Proofing Your Sales Team: Ongoing Development

Integrating Continuous Learning

I've spent two decades building sales teams, and one truth stands out: the best teams never stop learning. When I helped a mid-size SaaS company revamp their sales strategy, it was clear the reps needed more than just quarterly training sessions. They needed continuous learning. We integrated bite-sized learning modules right into their daily workflow. Reps could tackle these modules in between calls, constantly sharpening their skills while staying in flow.

This approach transformed their team of twenty into a powerhouse, closing $10 million more in annual revenue. They stopped seeing training as a burden and started treating it as an essential part of their workday. Why? Because they were faced with real world scenarios that demanded creative solutions, drawn from ongoing education.

Continuous learning isn't just about skills; it's about keeping your team agile. Technology changes, markets shift, and reps who aren't learning get left behind. As I've learned from Harvard Business Review, sales is an evolving field. Those who succeed adapt seamlessly.

Creating a Culture of Feedback

Feedback can make or break your team. I've seen sales managers throw numbers at reps, but real improvement comes from two-way dialogue. I recall one enterprise B2B client struggling with high turnover. They had a massive team but were losing clients as fast as they gained them. The missing link? Constructive feedback.

We implemented structured feedback sessions, using data from our 85 question assessment to guide discussions. These sessions weren't just about correcting mistakes; they were about understanding competitive wiring and leveraging it to align roles better.

• Weekly one-on ones focused on individual challenges.
• Monthly group meetings shared broader insights and fostered collaboration.
• Quarterly reviews incorporated feedback from clients to connect performance with customer satisfaction.

The result? A 30% reduction in turnover and a revived, vibrant sales culture. My experience shows that when feedback is ongoing and authentic, reps thrive.

Empowering Reps with Ownership of Their Growth

Development isn't top down; it's most effective when reps own it. I've watched companies excel when they trust their reps to take charge of their growth. One of my clients, a tech startup with a lean team, crafted individual development plans based on our 8-section report. Each rep identified specific areas to improve, such as conversion tactics or customer relationship depth, and took initiative.

This ownership model not only motivated them but also aligned their growth with the company’s goals. The startup doubled its client base within a year, a testament to what happens when reps feel empowered and accountable.

Empowerment in sales isn't about letting go; it's about guiding reps to use their competitive wiring to own their success. This mindset keeps teams dynamic and ready for future challenges.

Future-proofing isn't just a strategy; it's a commitment to resilience and growth, informed by real world inputs and practiced daily. In my 101 team builds, this ethos has consistently led to sustained success.

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