The Coaching Conundrum—Why Sales Leaders Fail to Develop Their Team


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In this episode of the Sales Leadership Awakening podcast, Steven Rosen and Colleen Stanley discuss the coaching conundrum sales managers face. They emphasize effective coaching in driving sales performance and highlight the impact of formal coaching processes on win rates and overall team success.

Steven and Colleen also discuss the key strategies and frameworks for creating a coaching culture that fosters continuous improvement and empowers sales teams to master essential skills. 

“Coaching is a tricky skill that needs to be understood and learned over time. However, it mostly becomes another item on a company’s to-do list and usually falls to the bottom.”  – Steven Rosen

Key Takeaways:

  • Lack of accountability and effective coaching are major obstacles sales leaders face in developing their teams.
  • Sales managers should focus on skill mastery by honing in on one or two key areas for improvement rather than trying to coach the entire sales process.
  • Consistent coaching sessions and pre-briefing sessions are instrumental in enhancing sales team performance.
  • Effective coaching leads to higher win rates and improved sales performance, while inadequate coaching can result in burnout, low morale, and increased turnover.
  • Regular coaching, focusing on skill development, and implementing a structured coaching methodology are key to creating a coaching culture and driving sales success.
The interactive podbook below contains videos, audio, articles, summaries, transcripts, and YouTube shorts from this podcast episode.

Full Episode Article:

Title: The Coaching Conundrum—Why Sales Leaders Fail to Develop Their Team”

Byline: By sales leadership and coaching experts Colleen Stanley and Steven Rosen


In the Sales Leadership Awakening podcast, Steven Rosen and Colleen Stanley discuss the coaching conundrum faced by sales managers and its effect on driving sales performance. They highlight the impact of formal coaching processes on win rates and overall team success. This article will delve into the key insights from the podcast and explore the themes of the importance of effective coaching, the impact of ineffective coaching, the connection of coaching to avoiding burnout among the themes, and the key to overcoming the coaching conundrum.

The Importance of Effective Coaching in Sales Leadership

Coaching is often recognized as critical to driving performance in the fast-paced sales world. However, many sales leaders struggle to effectively coach their teams, leading to a significant gap between knowing the importance of coaching and actually implementing it. This dilemma, the coaching conundrum, can have far-reaching implications for sales teams and their overall success.

The Impact of Ineffective Coaching

One of the key insights from the discussion is the significant impact of ineffective coaching on sales teams. Studies have shown that companies with a formal coaching process achieve a 28% higher win rate than those without, highlighting the importance of a structured approach to coaching. Additionally, even if coaching is not of the highest quality, it can still improve performance by 17%, underscoring the value of consistency in coaching efforts.

Avoiding Burnout and Maintaining Morale

Another crucial aspect discussed is the link between effective coaching and preventing burnout among sales teams. Burnout often occurs when individuals feel they are not making progress, and the lack of effective coaching can contribute to this feeling of stagnation. By providing consistent and meaningful coaching, sales leaders can help their teams stay motivated and engaged, ultimately leading to higher morale and productivity.

Nurturing a Culture of Support and Development

Ultimately, the key to overcoming the coaching conundrum lies in nurturing a culture of support and development within sales teams. By investing in training, implementing a formal coaching process, and holding managers accountable for their coaching efforts, organizations can create an environment where salespeople feel valued, supported, and equipped to succeed. This approach leads to improved performance and fosters a sense of motivation and engagement across the team.


In conclusion, effective coaching is a cornerstone of success in sales leadership. Many managers fail to coach effectively due to a lack of training and accountability, often relegating coaching to the bottom of their priority list. However, evidence shows that consistent coaching significantly enhances performance, as shown by dedicated managers prioritizing coaching despite busy schedules. This dedication keeps the team on track and drives substantial sales growth, demonstrating the critical impact of coaching on a company’s success.

Sales leaders must recognize the importance of coaching, implement structured methodologies, and ensure accountability to make coaching a consistent practice. High-level executives, such as CROs and VPs of sales, play a vital role in enforcing these practices by providing training and tracking coaching activities. By embedding coaching into the core responsibilities of sales managers and treating it as a key performance indicator, organizations can foster long-term development and achieve exceptional results, navigating the ever-evolving sales landscape with a well-coached, high-performing team.

Republished with author's permission from original post.

Colleen Stanley
Colleen Stanley is president of SalesLeadership, Inc. a business development consulting firm specializing in sales and sales management training. The company provides programs in prospecting, referral strategies, consultative sales training, sales management training, emotional intelligence and hiring/selection. She is the author of two books, Emotional Intelligence For Sales Success, now published in six languages, and author of Growing Great Sales Teams.


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