Coaching

When Sales Superstars Become Mediocre Leaders

The core of the problem is deceptively simple: Leading is not selling. 

A top-tier sales performer knows how to hit a number. They are driven, persuasive, and often thrive in a competitive, high-stakes environment. But leadership requires an entirely different set of attributes—ones that must be developed over time. It’s no longer about the rep’s ability to individually “win”; it’s about enabling others to win. 

In other words, the characteristics that made a rep great at selling can work against them as a leader. This is because: 

• Selling is about controlling the outcome and leadership is about coaching others toward it.  
• Selling is about execution and leadership is about vision.  
• Selling is about “me” and leadership is about “we.” 

Key Mindset Shifts: 

• From “I own the result” to “I coach to the result” 
• From self-reliance to team reliance 
• From execution to vision 
• From being the hero to creating heroes 

Even the most confident new leaders experience some version of this drop. They find themselves overwhelmed by ambiguity, unsure how to delegate, and lacking the framework needed to coach effectively. New leaders who were once excelling as reps must now grow in aptitude for an entirely new job. 

Warning Signs of B-Level Leadership:

• Telling rather than coaching 
• Inconsistent accountability 
• Doing the work for others 
• Avoiding difficult conversations 
• Focusing on tactics over strategy 

These are not signs of failure—they’re signs of being early in the journey. But left unaddressed, they result in long-term mediocrity. 

So, why do some highly successful sales reps flop as leaders? 

The challenge isn’t just skill-based. It’s psychological. Many successful sales reps unconsciously resist the transition from individual contributor to team leader. 

Common Pitfalls:

• The “I’ll just do it myself” syndrome: They’re so used to taking ownership that delegation feels like weakness. 
• The ego factor: Their identity is tied to personal success, not team success. 
• Blind spots from past success: What worked for them isn’t always replicable—and they struggle to teach what they’ve never had to break down. 
• Lack of organizational navigation skills: New leaders often underestimate how much of their role is about internal advocacy and influence (working the inside). 
• Struggling with strategic thinking: They’ve been rewarded for executing flawlessly, not for stepping back to see the big picture. 

Recognizing these tendencies is the first step to growth. But it also requires humility—a willingness to start over, despite past success. 

The Internal Transition Challenge

Most new leaders won’t say it out loud, but they’re thinking it: “I don’t know what I’m doing.” 

And that’s okay. That’s normal. In fact, every new leader begins as a “low B” on the Performance Matrix (moderate attitude, low aptitude) simply because they’ve never led before. They have to earn their way back up. 

Key Learning Curve Moments:

• Making hiring decisions that impact team dynamics 
• Putting someone on a performance plan 
• Having to terminate an employee with empathy and professionalism 
• Coaching someone who doesn’t think or work like they do 

Without these experiences—and the support to learn from them—new leaders remain stuck, often burning out or retreating to the comfort zone of execution. 

Making Coaching Time a Priority 

Second-line leaders juggle countless responsibilities—operational meetings, customer interactions, and unexpected crises that constantly demand attention. Amidst these pressures, the simplest yet most powerful coaching tool remains allotting dedicated time. 

Without intentional scheduling, coaching often becomes an afterthought rather than a strategic priority. Hinds emphasizes that second-line leaders must “inspect what you expect” by regularly reviewing coaching reports and development plans. This deliberate focus signals the importance of coaching while providing opportunities to reinforce good practices and course-correct when needed. 

What Top Leaders Do Differently

Great leaders build capacity and create environments where teams thrive, consistently and sustainably. 

Core Behaviors of ‘A’ Leaders:

• Coaching over telling: They ask the right questions instead of giving the right answers. 
• Clear accountability: They drive performance through clarity, not pressure. 
• Strategic decision-making: They think beyond today’s fires to tomorrow’s outcomes. 
• Vision and purpose: They inspire, align, and motivate with more than just targets. 
• Frameworks and systems: They build structures that help teams scale without them having to be in the room. 

Breaking the Pattern—Development Pathways for Mediocre Leaders

Nearly every new leader starts out as a solid ‘B’. However, with the right development, coaching, and exposure to challenges, many new leaders can grow into outstanding ones if intentional about it. 

What Development Looks Like:

• Structured skill-building paths: Not just product training but leadership skill-building (coaching, accountability, emotional intelligence) 
• Mentorship, modeling, and coaching: Pairing new leaders with experienced  leaders who can share insights and support 
• Real challenges: Rotational assignments, special projects, or temporary team leadership roles 
• Deliberate practice: Encouraging leaders to intentionally work on one leadership skill at a time (e.g., giving feedback, facilitating team meetings) 
• Regular feedback loops: Using tools like the Performance Matrix to measure growth in both aptitude and attitude 

Conclusion 

Top sales performers are valuable assets. Turning them into great leaders requires more than a title and a new comp plan. It requires a rethinking of how leadership potential is identified, developed, and supported. 

Organizations that invest in developing their leaders gain a massive competitive edge. Not just in numbers but in culture, retention, and the ability to scale. Because when leadership works, everything works.