Why Your Sales Team Is Underperforming (And How Next-Gen Leadership Coaching Can Fix It)
The Sales Leadership Blind Spot
You’ve hired skilled sales reps, invested in training, and set clear expectations—yet your team keeps their missing quota. Sound familiar? Many sales managers and business owners find themselves stuck in this frustrating cycle, trying every incentive and training session but seeing minimal improvement in motivation and performance.
As a sales leader with over 30 years of experience, I’ve watched many businesses struggle with this exact dilemma. A few years ago, I saw a trend in sales organizations. No amount of incentives or commission strategies seemed to help some companies increase their sales. It wasn’t until I had a fantastic conversation with the owner of a company I was working with that changed how I viewed sales management. This business owner shared that he had changed his strategy with his sales team from managing performance to a coaching strategy, and sales turned around.
The truth? Underperformance isn’t always a talent issue—it’s often a leadership challenge. And the fix isn’t just more training; it’s a next-generation approach to leadership coaching.
In this article, we’ll break down five key reasons your sales team may be underperforming—and how to fix them using modern coaching techniques that resonate with leaders today.
You’re Treating the Symptoms, Not the Cause
The Problem: Misdiagnosing Underperformance
Most sales leaders focus on the symptoms of poor performance—low close rates, missed targets, and declining motivation. But these are just surface-level indicators of deeper issues, such as:
Unclear expectations – Sales reps aren’t sure what success looks like.
Weak pipeline management – Deals are getting stuck, but no one knows why.
Lack of ongoing coaching—Training is treated as a one-time event instead of continuous learning, which is part of the organization's culture.
Low accountability – Poor performers are allowed to coast, dragging the team down.
The Solution: Data-Driven Leadership Coaching
As a leader, your first job is identifying the root cause of performance issues. Instead of assuming, start analyzing:
✅ Review sales calls – Are your sales reps asking the right questions or just pitching features?
✅ Track deal progression – Is your sales team consistently losing deals at the same stage?
✅ Run performance audits – Is your sales team struggling with mindset, skills, or motivation?
The business owner I interviewed shared that when he started leading with data instead of assumptions, he quickly realized his sales team wasn’t closing, which made him dig in further to find the root cause and what he discovered was they lacked confidence in handling objections—and not because they were lazy ( as he had initially assumed). He decided to start coaching through role-playing real-life objections; this hands-on approach made an immediate difference. This story resonated with me as early in my own sales career; the organization I worked for did role-playing 5 days a week at their daily sales meetings. While initially I didn’t want to participate because I was embarrassed, I quickly realized how powerful role-playing was and how it dramatically increased my close rate.
2. You’re Managing Instead of Coaching
The Problem: Micromanagement Kills Performance
Many sales leaders think managing and coaching are the same—they’re not. Managing is about tracking metrics, while coaching is about building relationships and developing people skills.
🔻 The Old-School Approach – Focused on reports, quotas, and reviewing numbers.
✅ The Next-Gen Approach – Focused on mindset, skill development, and behavioural change.
Micromanagement creates a fear-based culture where sales reps hesitate to take the initiative. A coaching culture, on the other hand, builds confidence and self-sufficiency.
The Solution: Shift to a Coaching Mindset
Here’s how to transition from managing numbers to coaching people:
✔️ Ask more, tell less – Instead of dictating solutions, ask your sales reps, “What’s stopping this deal from closing?”
✔️ Schedule weekly 1:1s – Make them coaching-focused, not just pipeline reviews.
✔️ Use the GROW model – Guide reps through Goals, Reality, Options, and Will to solve their challenges.
When I started role-paying early in my sales career, my sales skyrocketed. I rose to be a top performer nationally.
3. Your Sales Training Is Outdated
The Problem: A One-Size-Fits-All Approach No Longer Works
A multigenerational sales team means different learning preferences:
Gen X sales reps prefer structured, detailed processes.
Millennials learn best through collaboration and real-time feedback.
Gen Z sales reps expect bite-sized, tech-driven learning (key tip: these workers are just entering the workplace).
Yet, here we are in 2025, and most sales training programs are static. Worse yet, they were developed in the 1980s with a one-size-fits-all approach that sales reps forget within a week of training.
The Solution: Modernize Sales Training Through Coaching
🚀 Ditch outdated training methods – Replace long lectures with real-world role-playing and coaching-based learning.
🚀 Leverage technology – Use technological sales coaching tools to provide instant feedback on sales calls.
🚀 Encourage peer learning through mentorship – Have senior team members mentor junior ones to create a self-sustaining coaching culture.
The shift from "sit-and-listen training" to "interactive coaching" can immediately transform your team's ability to apply new skills.
4. Your Team Lacks the Right Motivation
The Problem: Sales Motivation Isn’t Just About Money
Many leaders assume more significant commissions = better performance. But today’s sales reps—especially Millennials and Gen Z—are motivated by more than just a paycheck.
🙅♂️ The old-school thinking: Pay more, get more effort.
✅ The reality: Sales Reps want growth, recognition, and a sense of purpose.
The Solution: Create a Purpose-Driven Culture
🔹 Celebrate wins beyond revenue – Recognize deal progression and relationship-building skills.
🔹 Incorporate career development – Show sales reps a clear path to leadership.
🔹 Build intrinsic motivation – Help your sales teams connect their work to a bigger mission (e.g., “We don’t just sell products; we solve real business problems.”).
5. Your Team Is Selling Features, Not Value
The Problem: Focusing on Features Instead of Solutions
Many sales teams still rely on outdated, product-heavy pitches, leading to:
❌ Feature dumping – Overwhelming prospects with information.
❌ Low differentiation – Sounding like every competitor.
❌ Poor objection handling – Losing deals when faced with price pushback.
The Solution: Shift to Consultative Selling
🔹 Teach sales reps to diagnose first sell second – Ask deep-dive questions before pitching.
🔹 Reframe objections as opportunities – Train sales reps to uncover hidden needs instead of reacting defensively.
🔹 Role-play real sales scenarios – Practice how to pivot conversations from "Here's what our product does" to "Here's how we solve your problem."
I have worked with many clients who have struggled with closing sales. Their challenge? They are too focused on their service or product details, which results in them dumping all over their customers. I encourage leaders to ask better discovery questions, speak less, and learn more.
The Future of Sales Leadership Is Coaching-Driven
If your sales team is underperforming, it’s not about working harder but leading smarter.
🚀 Diagnose why your sales reps are struggling instead of assuming.
🚀 Shift from managing numbers to coaching performance.
🚀 Modernize training to fit how today’s salespeople learn.
🚀 Motivate beyond money—focus on growth, recognition, and purpose.
🚀 Help sales reps sell solutions, not just products.
Sales leadership has changed. The leaders who embrace coaching as their core strategy will be the ones who build high-performing, resilient sales teams.
📌 Want to learn how The Confident Close™ can elevate your sales leadership? Let’s connect! 🚀
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