Cultivating a Winning Mindset with Josh Horstmann

Why Even Your Best Salespeople Need Coaching

There’s a dangerous myth in sales leadership—one that quietly erodes performance, disengages top talent, and stifles growth.

It’s the belief that coaching is only for struggling reps.

Josh Horstmann, Operating Partner at Francisco Partners Consulting, tackled this misconception head-on in a recent episode of the Coach2Scale podcast. He made one thing clear: coaching is not a remedial exercise. It’s the key to unlocking the full potential of every sales professional, from new reps to seasoned executives.

If your coaching efforts focus only on struggling performers, you are neglecting your biggest opportunity for growth.

The Best in the World Have Coaches—Why Don’t You?

There’s a paradox in sales leadership. While elite athletes, world-class performers, and industry leaders all rely on coaches, many sales professionals assume they’ve outgrown the need for coaching once they reach a certain level.

But the reality is different, even the best need coaches—not because they are failing, but because they are constantly looking for ways to improve.

Horstmann pointed to examples like Tiger Woods, Tom Brady, and UFC champion Jon Jones. Each of them has multiple coaches guiding them through every stage of their career. And yet, in sales, the moment a rep becomes an “A player,” a manager, or even a CRO, coaching often disappears.

The assumption is that success at one level automatically translates into mastery at the next. But that’s rarely the case.

Why Your Best Reps Still Need Coaching

Most managers devote their coaching time to underperformers, trying to bring C players up to a passing level. Meanwhile, top performers are left to navigate their careers on their own. That’s a mistake.

High performers still need guidance. They just need a different kind of coaching—one focused on long-term development rather than immediate deal execution.

A players don’t need someone micromanaging their sales motions. They need mentorship on leadership, negotiation, strategic thinking, and career progression. They need a manager who can help them refine their craft and push them beyond their current capabilities.

Failing to coach top performers sends a clear message: your development is not a priority. And when that happens, your best reps start looking elsewhere.

The Coaching Trap: Why Most One-on-Ones Are Failing

Horstmann identified another common problem: even when coaching does happen, it often becomes just another forecast review.

Instead of true skill development, one-on-ones become pipeline status updates. Managers ask about deals in the pipeline, reps provide updates, and the meeting ends. This is not coaching.

A coaching conversation should be structured, skill-based, and forward-looking. It should focus on areas of growth—whether that’s refining prospecting skills, mastering negotiation tactics, or preparing for leadership roles.

Yet, all too often, coaching sessions are rescheduled, deprioritized, or turned into last-minute deal triage. The result? Reps don’t feel invested in, and managers miss the opportunity to build long-term capability within their teams.

The Mistake of Promoting Star Reps to Management

One of the biggest missteps in sales leadership is assuming that top individual contributors will naturally make great managers.

Horstmann has seen this mistake play out repeatedly: a star rep is promoted into leadership, but instead of developing their team, they become a super closer. Instead of coaching, they step in and take over deals.

This happens because selling and coaching are two completely different skill sets.

Great sellers know how to hit their number. Great coaches know how to develop others so that the entire team can hit its number.

Before promoting a top rep into management, sales leaders need to assess whether they are prepared to coach and scale a team. Otherwise, they risk turning their best individual contributor into an overwhelmed and ineffective manager.

Building a Leadership Pipeline: The Power of a Virtual Bench

When a management position opens up, many sales leaders scramble to fill the role—often by promoting the nearest available A player.

Horstmann warns against this reactionary approach. Instead, he recommends building a virtual bench—a proactive pipeline of internal and external talent who are prepared to step into leadership roles when the time comes.

This means identifying potential leaders early, giving them team lead responsibilities, and ensuring they receive coaching on management skills before they are formally promoted.

With a strong virtual bench, sales organizations can ensure that when leadership roles open, they have a well-prepared candidate ready to step in—not just a top performer who was next in line.

Coaching as a Competitive Advantage

Coaching is not an optional activity or a reactive measure for underperformance. It is a strategic lever for retention, quota attainment, and long-term success.

Organizations that embed coaching into their culture see measurable improvements:

  • Lower attrition rates
  • Higher quota attainment
  • Increased engagement and job satisfaction
  • A stronger pipeline of future leaders

The best sales teams make coaching a non-negotiable part of leadership.

How CoachEm Helps Sales Leaders Build a Coaching Culture

CoachEm was built to solve this exact problem. As the world’s first AI-driven coaching execution platform, CoachEm ensures that coaching is structured, data-driven, and focused on long-term skill development, not just deal reviews.

With CoachEm, sales leaders can:

  • Identify skill gaps at the individual and team level
  • Provide structured, personalized coaching based on real performance data
  • Ensure that one-on-ones are productive, focused, and actionable
  • Develop a coaching culture that retains top talent and drives performance

If you’re ready to move from reactive deal coaching to proactive skills development, it’s time to rethink your coaching strategy.

Contact a human at CoachEm to start building a culture of coaching that retains and elevates your best people.