Navigating the Sales & Leadership Skill Set Divide

Salespeople struggle at leading because these require different skill sets. These skill sets reinforce distinguishable and seperate roles within sales forces.

In the fast-paced sales landscape, professionals often strive to achieve impressive results and rise through the ranks, from top performers to sales managers to VP of Sales. However, transitioning from a top-performing salesperson to an effective sales leader can be challenging and sometimes impossible. 

So, why do salespeople struggle to lead? Salespeople struggle to lead because the skills for sales and leadership differ. Great sales traits like goal orientation, self-serving attitudes, and quick thinking don’t always align with leadership qualities such as organization, mindfulness, and foresight. Success in one doesn’t guarantee the other.

This article will explore salespeople’s common struggles in leadership positions and delve into the unique skills required for both roles. 

sales hiring and sales team

Sales Success Doesn't Guarantee Sales Management Prowess

The belief that a successful salesperson will naturally become an effective leader is a common misconception. While outstanding sales performance may indicate a strong work ethic, resilience, and adaptability, these traits alone do not guarantee success in a leadership role. 

Top performers can suffer from the “super salesperson syndrome,” unable to detach from the rush of winning deals and assume one professional identity. The result— is a dive in productivity, disgruntled salespeople start heading for other companies, and the new sales managers or leaders are dismissed. 

Specific skills and qualities required for effective leadership, such as empathy, strategic thinking, and team-building, must be intentionally developed and nurtured in sales forces. 

Individuals and business departments need to recognize that the transition is not automatic and is more often unsuited.

By dispelling this myth, sales organizations can better fulfill senior management roles and prepare their sales professionals for potential leadership opportunities. 


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Difference Between Sales Skills and Leadership Skills

Sales skills are developed through understanding customers, identifying their needs, and persuading them to purchase. Sales reps require excellent communication, negotiation, and problem-solving abilities.

Salespeople often excel in fast-paced sales teams where they must think on their feet and adapt to changing situations.

Below are examples of ten skills for top-performing salespeople:

  1. Effective communication, active listening, and presentation skills
  2. Relationship building, empathy, and customer service orientation
  3. Persuasion, negotiation, and objection handling
  4. Product knowledge and market/industry awareness
  5. Time management and adaptability
  6. Resilience, goal orientation, and self-motivation
  7. Problem-solving, critical thinking, and decision-making
  8. Networking, social skills, and collaboration
  9. Customer-centric approach and understanding
  10. Demonstrating and promoting product value
sales team and sales leader

On the other hand, leadership skills encompass the ability to motivate, guide, and manage a team toward a common goal. Compelling leaders can create a vision, delegate tasks, and foster a positive work environment that encourages collaboration and growth.

While there are certainly some overlapping qualities between successful salespeople and leaders, such as effective communication and a results-driven mindset, the core competencies of each role are fundamentally different. This distinction highlights the need for tailored development plans for individuals transitioning into management responsibilities and guides best practices for hiring for the sales leader role.

The best sales leaders have these skills sets, which differ from other sales team members: 

  1. Strategic thinking, planning, and prioritization
  2. Team building, motivation, and delegation
  3. Empathy, emotional intelligence, and relationship building
  4. Effective communication and active listening
  5. Coaching, mentoring, and performance management
  6. Conflict resolution, negotiation, and decision-making
  7. Problem-solving and adaptability
  8. Time and resource management skills
  9. Business acumen, talent management, and market awareness 
  10. Fostering a collaborative, inclusive work environment, and networking
sales team with sales leader

Difference Between Sales Skills and Leadership Skills

Salespeople are often highly goal-oriented and self-serving, focusing on personal targets and striving for individual success. While this drive can lead to impressive sales results, it may translate poorly into a leadership role.

Leaders need to prioritize the well-being and success of their team members, creating a supportive environment that promotes collective achievements.

Self-serving traits can be detrimental to effective leadership, as they may cause leaders to prioritize their interests over the needs of their team.

To develop a more inclusive and supportive leadership style, individuals transitioning from sales to management roles should focus on empathy, active listening, and a genuine interest in the growth and development of their team members.

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Promoting your Best Salespeople

Promoting sales managers and sales reps to a new professional identity in senior management is a common hiring misstep

When considering the promotion of top performers to a sales manager or VP of Sales role, it is crucial to evaluate several factors beyond their sales success:

  • Sales vs. leadership skills: While a candidate’s sales talent is essential, it doesn’t necessarily equate to possessing leadership abilities. Assess whether they have the required team-oriented skills and adaptability for a leadership position.
  • Impact on performance: Promoting a high-performing salesperson might remove your most valuable independent contributors, preventing your team from making broader contributions to team quotas. 
  • Career growth: So many salespeople aim for career advancement opportunities. Failing to provide a path to leadership might lead them to pursue opportunities elsewhere. However, promoting them only if they possess the necessary leadership skills is essential.
  • Assessing sales proficiency: The sales leader must be the best salesperson on the sales team. Validate the sales manager’s sales abilities through a thorough interview to ensure they possess the required skills and experience.
  • Avoid promotion for promotion’s sake: Refrain from promoting high performers solely based on their sales performance, as their strengths in sales may not translate to leadership effectiveness. Instead, focus on evaluating their potential and aptitude for a leadership role.

By carefully considering these factors, founders and CEOs can make informed decisions when promoting sales managers to VP of Sales positions, ensuring the right fit for both the individual and the organization. 

Soon-to-be managers can benefit from targeted training programs, mentorship, and opportunities to practice and refine their leadership skills in real-world settings.

If you choose to promote sales managers and reps from your sales force, sales firms play a vital role in fostering the right skill set for management trainees. Setting sales managers up for success includes resources, support, and a culture encouraging personal and professional development

Hiring For VP of Sales Roles

To excel in sales leadership, individuals need to strike a balance between their existing sales expertise and the development of leadership competencies.

Hiring the best candidate for your VP Sales role involves recognizing the company and the sales organization’s unique challenges and demands and acknowledging the need for continuous learning and growth.

Hiring a sales leader with the right skill set is crucial for the success of your sales team and overall business profitability.

For instance, consider a fast-growing startup requiring a sales strategy focused on exploration, experimentation, and flexibility. If the startup hires a sales manager with impressive experience in established companies but needs more adaptability, it may struggle to attract new business and meet revenue targets.

Early identification and correction of this mismatch can prevent the worst-case scenario.
In another example, established technology companies hire new managers with aggressive leadership styles. Although the sales organization consistently meets revenue targets, the staff turnover rate increases, leading to the loss of top talent to competitors. This situation negatively impacts the business, staff members, culture, and reputation.

The best-case scenario involves the founder addressing the culture imbalance and redirecting the VP of sales. If left unchecked, the company may lose its best sellers and struggle to compete with rivals.

Thus, selecting sales managers with the appropriate skill set is essential for long-term success and for fostering a healthy work environment.

sales leader speak with prospect and sales team

Selecting the right candidate is crucial, as the job requires leaders to:

  1. Offer clear guidance and demonstrate a comprehensive understanding of the business.
  2. Implement sales processes that emphasize customer experience.
  3. Instill and promote core business objectives, values, and mission.
  4. Strengthen existing customer relationships and foster connections with potential clients.
  5. Develop a sales playbook for consistent and predictable sales growth.
  6. Create a scalable and replicable sales hiring profile.
  7. Nurture talent while reducing turnover, particularly among top talent.
  8. Prioritize recruiting, developing, and retaining team members.
  9. Boost motivation among sales managers, sales reps, and support staff.
  10. Drive revenue growth and elevate performance across sales reps and managers.

Do you have a winning sales strategy?

Understanding why salespeople struggle to lead is essential for businesses seeking sales leadership positions. The skills that make them exceptional in sales only sometimes translate to effective leadership.

Transitioning from a top-performing salesperson to a successful sales leader requires different abilities, including strategic thinking, team building, and adaptability.

Recognizing these differences and nurturing the right skill sets are crucial for a smooth transition and the organization’s success. If your business seeks support addressing why salespeople struggle to lead, consider partnering with our Rose Garden Consulting.

Our team of experts can help identify and develop the right leaders for your organization.

Get started with a Team Assessment to evaluate and improve your team dynamics, or dive in with our Sales Accelerator to boost your sales performance.

Don’t let the challenge of finding the perfect sales leader hold your business back –discover how Rose Garden can help you reach new heights in sales success.


Ali Mirza

About the author:

Ali Mirza is the Founder & CEO of Rose Garden, a national sales consulting organization, and featured in Forbes, Inc, Business Insider, The Huffington Post, Business Rockstars, and The Wall Street Journal.

Ali is a highly sought-after public speaker presenting at multiple national conferences on innovative ways to accomplish transformational growth on your sales team.

Rose Garden provides unparalleled support and guidance to growth-minded founders via sales strategy differentiation, world-class sales culture creation, and exclusive playbooks, processes, and scripts to position them for limitless growth.

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