This article was originally published by MonitorDaily in September 2023.
Reprinted with permission from the author.

Many companies struggle with systemic issues in the expectations, training, onboarding, development process and even hiring of salespeople. Deborah Reuben, CEO and founder of TomorrowZone, sat down with Kelly Riggs, author, speaker and executive business consultant, to discuss his perspective on the “un-training” of salespeople in order to greatly improve corporate leadership and sales performance.

Renowned futurist Alvin Toffler wrote, “In the 21st century, illiteracy won’t result from an inability to read and write, but from a failure to learn, unlearn and relearn.” Leaders are challenged to build culture and enhance performance in a rapidly changing work environment. Fixed mindsets hinder innovation and adaptation. We must be open to new behaviors, skills and mindsets, and embrace new approaches to succeed.

To delve into this, I sat down with Kelly Riggs, author and dynamic thought leader in the fields of leadership, sales development and strategic planning. We explored his groundbreaking Sales UNTraining approach to enhancing corporate leadership and sales performance. The following is our interview condensed and rephrased for conciseness.

Can you share your background and the journey that led to what you do today?

Kelly Riggs: I initially pursued electrical engineering, despite my mathematical abilities, and I quickly realized it wasn’t for me. At 20, I left college, got married and stumbled into my first sales job. Having limited exposure to business, I was quite ignorant about selling but found it fascinating and dove in.

I excelled in the orthopedic field, becoming a back-to-back national salesperson of the year. Transitioning into management, I realized my lack of expertise. I’m not really satisfied with being mediocre, and pursued improvement. I went on to do speaking, coaching and consulting in the corporate world.

After a startup stint, a friend asked for help in leadership, knowing my background in speaking and coaching. I enjoyed the consultative process. So I established my company, The Business Locker Room, in 2005.

I believe business, especially sales, is a competitive arena where only the best succeed. With a background in sports coaching, I thrive on helping and coaching others. Over the past 18 years, my focus has expanded beyond sales to include leadership, team development and strategic planning, all interconnected aspects of success.

How would you describe what you do today?

Riggs: Sales UNTraining is the culmination of my frustration after 18 years of closely working with sales teams, CEOs and business owners. Many of them express dissatisfaction with their sales results, especially during economic downturns or market challenges. This struggle often arises from systemic issues in our training, onboarding and development processes for salespeople. The data shows that only around 6% of salespeople are truly exceptional, while a significant portion, roughly 75%, fall short in various ways. These problems are pervasive and systemic, affecting the entire approach to representing our companies and products in the field. This issue extends beyond the sales department and would be unacceptable in any other aspect of corporate America. My recent “Sales UNTraining” podcast launch underscores my commitment to addressing and rectifying these systemic deficiencies.

What is Sales UNTraining?

Riggs: Sales UNTraining is about challenging conventional approaches and embracing the opposite of what’s currently done – hence the term “untraining.” It’s unlearning old ways and relearning new ones, a fundamental shift. Many companies struggle with training, often focusing on superficial checkboxes rather than deep transformations.

When discussing sales training, the common surface-level concerns, like closing techniques, are addressed. However, true change requires a profound shift in behavior and skills. The aim is consistency, continuity and impactful behavior change, which isn’t achieved through conventional methods like digital modules or classroom sessions.

Consider a scenario: You become skilled at closing deals, but what if you’re engaging with the wrong person or misunderstanding their needs? Context matters immensely. Mere skills training without behavioral change and context is insufficient. The current $70 billion annual investment in sales training within corporate America isn’t yielding desired outcomes.

Sales UNTraining is a disruptive approach that challenges this status quo. It’s a recognition that genuine success demands more than surface-level tactics; it requires a complete shift in perspective and behavior.

How can you effectively reinforce new skills and behaviors?

Riggs: It’s crucial to dissect this into systemic components. Many current leaders tend to apply tactical solutions to strategic issues, like the misdirected focus on closing. However, there’s a broader problem at play.

Consider sales training as an example. It’s not just about initial learning; effective coaching for ongoing improvement is essential. This process requires skilled sales leaders who can assess, coach and provide nuanced guidance. Without such leaders, training lacks the desired impact.

Drawing from my sports experience, effective coaching involves specific role-focused details, not vague exhortations. Merely promoting top salespeople to management can backfire. Many great salespeople lack coaching skills and process methodology needed for effective leadership.

Systemically, we often appoint managers who lack coaching inclination and skills to oversee training and development. This creates a disconnect, leaving us puzzled about underperformance. Too often, promoting the best salesperson to manager yields subpar management and the loss of a top sales performer.

This stems from systemic issues — insufficient preparation, lack of role transition expectations and inadequate leadership training. The complexity of these challenges becomes evident quickly.

How are generational differences and remote work impacting sales teams?

Riggs: To achieve remarkable, consistent revenue growth — something only about one in four organizations achieve — one must align focused leadership, unique talent and effective systems and processes. All three elements are interconnected and systemic.

Navigating generational differences is a significant factor. My co-authored book1 with my son delves into generational leadership’s impact on the workplace. The challenge emerges when older leaders, boomers and Gen X resist adapting to new realities. The real issue lies in leadership adaptability, not generational differences.

Each generation brings change, but leadership’s not generational, it’s relational. Relationship building requires adaptability by the leader. If I’m stuck in my ways, the way we’ve always done it, not innovating, or adapting, we’ll struggle.

In the landscape of remote work, this adaptability is more vital. While remote work affects other sectors, I’ve noticed a comparatively lesser impact on sales, given its inherent adaptability. Remote sales teams are a prime example; we operate successfully across locations.

In a multi-generational environment, the heart of effective sales management lies in understanding and nurturing the perspectives of team members. Building relationships requires time and investment. Without systemic focus on robust sales leadership and identifying and onboarding unique talent, problems inevitably arise. It’s the synergy of these components that drives enduring success.

How can leaders invite generational perspectives?

Riggs: There are a couple of key steps to consider. Many leaders overlook defining their culture, boundaries and desired standards when hiring. They focus on task-based job descriptions rather than discussing the core values, community impact and desired way of doing things.

Intentional relationship-building is often neglected, particularly in today’s remote work environment. We advocate weekly one-onone meetings with a structured template. This approach not only offers crucial feedback, something younger generations value deeply, but also fosters a foundation of trust.

Leadership hinges on influence, and trust is at its core. Without a relationship, trust is hard to establish. To invite generational perspectives, leaders must intentionally shape their culture and workforce vision. Building genuine relationships with team members is vital for securing their buy-in and aligning with the desired direction.

How can leaders build culture in a mixed-mode work environment?

Riggs: You’re playing a long game here, so often we want to band-aid problems. Building culture in a distributed workforce requires a strategic approach. Instead of quick fixes, true success comes from embracing a holistic view. Finding the perfect “born” salesperson or promoting a top performer doesn’t guarantee sustainable growth.

As companies expand, it’s not technical competencies but leadership competencies that determine failure or success. You must have an organizational structure that sustains growth. Emphasis shifts to soft skills, which are not secondary; they are the essence of effective teams. Hiring for technical skills is straightforward, but what truly matters are communicators with strong characteristics that align with core values.

Soft skills often take a backseat, especially in strategic planning. However, intentionally fostering a culture that values these skills and their impact is vital. Many organizations excel in their domain yet stink at growth and scale because they’re not building leadership capacity.

Today’s successful organizations must prioritize education and fostering leadership capacity. Those that don’t focus on becoming educational platforms for talent may find it challenging to survive in the current landscape.

What are you learning about now?

Riggs: Currently, I’m focused on understanding learning behavior. As coaches and consultants, we’re fundamentally in the business of driving behavioral change. By diving into fields like neuroscience, neurophysiology and digital technology, we can fine-tune the process of facilitating rapid behavior change. While personal motivation plays a role, conventional training often hinders effective learning, especially in areas like sales.

This exploration excites me. Emerging research offers fresh insights on this topic. Integrating artificial intelligence into this conversation is also intriguing, particularly content generation. Content alone, even AIgenerated, lacks impact without context and the human touch. The challenge is to merge AI’s efficiency with the human element to provide relevant and applicable insights within today’s corporate landscape. Balancing this interplay will undoubtedly shape the path forward.

What can professionals do today to shape a better tomorrow?

Riggs: I believe leaders can shape a better tomorrow by dedicating time today for deep thinking. This practice has been a hallmark of influential minds, especially in the technology and business realms. We strongly advocate setting aside a focused period, what we call a “leadership window.” Leaders can engage in pondering, considering new perspectives, reading and innovation.

This dedicated time allows leaders to isolate themselves from disruptions and distractions, honing in on core strategic leadership functions. Today’s leaders impact tomorrow’s outcomes through deeper levels of contemplation, paving the way for impactful change.

Current results stem from current actions. To transform outcomes, it’s not just about solving immediate problems but about addressing underlying structural and systemic issues. Therefore, leaders should invest more time in thoughtful consideration of these critical aspects.

1Counter Mentor Leadership: How to Unlock the Potential of the 4-Generation Workplace, by Kelly Riggs & Robby Riggs.


Kelly Riggs is a widely recognized author, speaker and executive business consultant in areas of sales, leadership and strategic planning. Riggs is a former award-winning sales executive, business owner and member of Forbes’ Coaches Council.

Deborah Reuben, CLFP, is CEO and founder of TomorrowZone, an innovative consulting firm bringing forward-thinking insights and original ideas to help companies adopt digital, gain efficiencies and design roadmaps for the future. She holds many industry leadership positions and authored The Certified Lease & Finance Professionals’ Handbook sixth to ninth editions.