MasterClass with Scott

Abstract 

This MasterClass features Scott, a seasoned professional in enterprise IT sales. Over the course of his career, Scott has generated over $100 million in sales, becoming a master in selling complex solutions to federal and commercial clients. His story is a testament to perseverance, adaptability, and the importance of disciplined action. This lesson focuses on essential sales strategies, the mindset needed to succeed, and how to turn challenges into opportunities. 

Detailed Narrative 

Like many people in our community, Scott grew up in challenge circumstances. In our video interview, which is a part of this lesson plan, Scott, described himself as being the youngest of three children. He grew up in an environment marked by financial instability and household dysfunction. His said that both of his parents lived as functioning alcoholics. They divorced while he was still young. To cope in that environment, he participated in sports and he excelled in baseball.

Baseball became Scott’s outlet and anchor. His athletic talent opened doors, exposing him to mentors—coaches who saw his potential and urged him to strive for more. A baseball coach encouraged Scott to break the cycle of struggle. If he invested in personal development, not only with sports, but also with school, he could open new opportunities.

That baseball coach gave Scott hope for a better life. It inspired him to pay attention in school and to learn more about steps he could take to advance his life. He chose to prepare for college, and he set a goal of becoming the first person in his family to earn a university degree. Education, he believed, would lead to new opportunities.

Scott didn't describe himself as a gifted student. He simply made a commitment to work through the lessons until he earned the credits necessary to advance. Determination to succeed, more than a love of the classroom, kept him going. To keep pushing forward, he reminded himself of the bigger picture, sensing that a college degree would open doors for him.

Scott’s story highlights the power of making the most of available resources, no matter how limited they may seem. For students without access to formal education or college-degree programs, the path to success still offers countless opportunities for growth. By participating in personal development initiatives, such as our master classes, students can gain valuable skills and knowledge to help them achieve their aspirations.

Tracking progress is a vital part of this journey. In a traditional college setting, students like Scott can develop an academic transcript that reflects their accumulated credits and satisfies degree requirements. However, students in our community may not have the same access to build such transcripts. Instead, they can leverage the tools our nonprofit offers and think creatively. By actively building their profiles on Prison Professors Talent, students can document their achievements, lessons completed, skills acquired, and progress made. These profiles serve as a powerful testament to their dedication, creativity, and resilience, offering a tangible record of accomplishment that stands alongside a traditional degree. Regardless of what the prison system offers, a person can work to develop story-telling skills, math skills, and build a record showing a commitment to self-directed learning. That record becomes an asset, one that a person can leverage later into new opportunities, just as Scott's story shows us.

By committing to their own growth and showcasing their value through sustained effort, students open the door to future opportunities. They position themselves to thrive, make an impact, and create meaningful change in their lives.

After college, Scott started his career in an entry-level, commission-only position, selling tickets for a comedy show at a local mall. The job didn’t require a college degree, as his earnings depended entirely on his ability to sell. It was a challenging role that forced him to develop the skill of striking up conversations with strangers. While he had the opportunity to shadow the company’s owner, who made the work seem effortless, Scott never quite found his stride in the role.

Scott shared a valuable lesson about his journey into the sales profession—a reminder of the universal importance of sales in every industry. Every business relies on customers purchasing products or services, and sales professionals play a vital role in connecting businesses with those customers. To develop skills in selling, however, a person must practice and persistence.

Much like an aspiring comedian stepping onto a stage for the first time, a sales professional must dive in, learn by doing, and refine their craft. Comedians test their material, gauge audience reactions, and adjust their timing until they master the art of making people laugh. Similarly, a successful salesperson engages potential customers, builds excitement, addresses objections, and ultimately closes the deal.

What looks effortless on the surface—whether in comedy or sales—is often the result of countless failures, lessons, and adjustments. Scott emphasized that sales is a numbers game. Facing rejection is inevitable, but it’s also part of the path to mastery. By embracing those challenges, salespeople can hone their skills, learn from experience, and ultimately achieve success. Although he had a short-lived experience selling comedy tickets, Scott learned valuable lessons about rejection, persistence, and the importance of honing one’s craft. 

Facing rejection is not the end but rather the beginning of growth and transformation. Every "no" offers the chance to learn, adapt, and build resilience—the very skills that drive personal and professional success.

For individuals in prison, navigating objections from others can be an opportunity to strengthen communication and persuasion abilities. These skills are invaluable, not only for eventual reintegration into society but also for initiating meaningful change during incarceration.

In Earning Freedom: Conquering a 45-Year Prison Term, I offer many examples of how I faced rejections in prison. Every person in prison hears the same message:

• You've got nothing coming.
• If you can't do the time don't do the crime.
• We don't care anything about your future, we only care about the security of the institution.

Many staff members in prison develop a special skill at denying requests. Yet every individual in prison must learn to overcome those objections. They must be persistent. If they document the effort, writing down the steps they took to grow in the face of adversity, they develop a skill that will bring value to the marketplace after release. As Scott told us, every product or service requires sales, and anyone who chooses to invest in personal development can build a meaningful career in sales.

By documenting instances where they have actively contributed to fostering trust—whether by helping prison administrators or working to shift perceptions within the judicial system—they demonstrate accountability, reliability, and potential. Overcoming objections in this manner can help pave the way for increased liberty and opportunities, serving as a testament to their growth and readiness for a second chance.

Scott transitioned from selling comedy show tickets face-to-face at the mall to trying his hand at telemarketing, where he ventured into the world of technology sales. During the electronics boom of the 1980s and 1990s, he took a desk job cold-calling potential clients, generating leads for senior salespeople. Over the next two years, he refined his ability to build rapport over the phone, mastering the art of connecting with people remotely. This experience became the foundation of his growing career. He not only developed the skills needed for effective prospecting but also deepened his knowledge of the products he sold. Through persistence and practice, he learned how to engage clients, foster meaningful relationships, and keep conversations going—skills that would prove invaluable in his professional journey.  

Eventually, Scott moved into the field of insurance sales. To advance his career in insurance sales, Scott had to commit himself to a rigorous process of learning and professional growth. The role demanded that he pass a state licensing exam, a critical step that would officially qualify him for the position.

Preparing to pass the licensing exam to sell insurance required hours of dedicated study. He needed to master complex concepts, a new language, and regulations specific to the insurance industry. Beyond the exam, Scott also invested significant time in understanding the intricacies of this new field. He immersed himself in learning about policies, risk assessment, and the nuances of customer service within the insurance sector. This effort marked a pivotal moment in his career, showcasing his determination to overcome challenges and succeed in a completely unfamiliar industry.

While selling group healthcare plans to small businesses, Scott learned the art of face-to-face selling, leveraging his growing interpersonal skills to build trust and close deals. He saw this role as a stepping stone, one that taught him to manage a different kind of rejection, requiring him to work continuously on improving his communication skills. He developed new storytelling techniques, and maintain a relentless focus on outcomes.

After a couple years in the insurance industry, Scott's career took a pivotal turn that steered him toward enterprise technology sales. The opportunity arose unexpectedly through a chance encounter with a former colleague who had transitioned from insurance to software sales. While on a layover at the Dallas airport, Scott ran into her and struck up a conversation. She spoke enthusiastically about her new career, sharing that she had recently been promoted to a management position. Seeing his interest, she asked if he would consider stepping into her previous role. Without hesitation, Scott seized the opportunity, setting the stage for the next chapter in his professional journey.

Scott easily navigated the interview process and, for the first time, began selling complex enterprise solutions to Fortune 1000 companies. These high-value deals demanded strategic planning, teamwork, and long sales cycles. Selling to companies making multi-million-dollar investments required Scott to adapt to an entirely new approach.

One key aspect of this process was participating in "four-legged" sales calls—a term I didn't initially understand when Scott mentioned it during our video interview. He explained that because the products were highly technical, each sales call involved two people: an engineer to handle the technical explanations, and a sales professional to focus on persuasive selling. This dynamic was new to Scott, and to get up to speed, he spent his first few weeks shadowing these meetings. With Scott observing, they became "six-legged" sales calls—three people, with two legs each, working together to close the deal. Sitting quietly in the corner, he observed, took notes, and absorbed everything he could to master this collaborative sales process.

His willingness to "learn the ropes" propelled his confidence and skill set, eventually earning him a spot on more sophisticated teams handling multimillion-dollar federal government deals. 

Throughout his career, Scott attributes his success to a robust action plan and a willingness to continuously adapt. Whether it was making cold calls, attending networking events, Scott understood the value of putting in the hard work. He emphasizes that awareness of one’s market, clients, and competition is key to staying relevant and competitive. 

When asked how he remained motivated, Scott referenced his early aspirations of financial stability and independence. He envisioned a future where he wouldn’t have to worry about making rent or covering bills. This authentic drive kept him focused even when the odds seemed steep. 

Today, Scott reflects on his path with pride and appreciation, grateful for the mentors and opportunities that shaped his journey. His advice to aspiring sales professionals, including those in challenging circumstances, is simple yet powerful: "Be a people person. People buy from those they like and trust. Work on your interpersonal skills, and the opportunities will follow." 

Lessons Learned from Scott 

1. Start small and demonstrate resilience—every role, no matter how minor, can lead to greater opportunities. 
2. Sharpen your skills through continuous learning and practice. Focus on communication, product knowledge, and building trust. 
3. Be intentional in networking—it’s not just about who you know but how you position yourself as a reliable and valuable connection. 
4. Master the art of perseverance. Sales, like life, is about persistence and seeing "no" as a step closer to "yes." 
5. Stay authentic and focused on creating value for others. 

Vocabulary Development 

1. Resilience – The ability to recover quickly from challenges or difficulties. 
2. Interpersonal – Relating to communication and relationships between people. 
3. Accountability – Taking ownership and responsibility for your actions and outcomes. 
4. Aspiration – A strong desire to achieve something great or significant. 
5. Prospecting – The act of identifying and reaching out to potential customers. 
6. Momentum – The driving force gained through consistent action and progress. 
7. Adaptability – The ability to adjust and thrive in changing conditions. 
8. Collaboration – Working effectively with others to achieve a common goal. 
9. Rapport – A positive and trusting relationship with others. 
10. Execution – The act of effectively putting plans into action. 

Self-Directed Reflection Questions 

1. How can defining your key aspirations guide your career or personal growth? 
2. What steps can you take today to build your communication and interpersonal skills? 
3. How can rejection strengthen your resolve and future opportunities? 
4. What lessons from Scott’s career resonate most with your current situation? 
5. How can self-directed learning prepare you for the workforce and overcome disadvantages? 
6. Why is authenticity important in building trust and achieving long-term success? 
7. How can networking help open doors and build lasting professional relationships? 
8. What actions can you take to hold yourself accountable for your progress? 
9. How can small achievements lead to larger opportunities over time? 
10. What strategies can you use to remain adaptable in the face of challenges? 

Recommended Books

"How to Win Friends and Influence People" by Dale Carnegie – Through real-life examples and actionable techniques, Carnegie teaches us how small gestures, like remembering someone's name or showing sincere appreciation, can leave a lasting impression. He also highlights the importance of active listening—not just hearing but truly understanding—which we've explored as a cornerstone of effective communication. Additionally, his focus on empathy mirrors the strategies we’ve practiced for understanding others' perspectives to create deeper, more collaborative relationships.

Carnegie's classic relates to the same lessons we learned from Scott in this master class, connecting theory with actionable steps. Carnegie’s principles of taking a sincere interest in others, offering thoughtful compliments, and fostering mutual respect serve as a practical guide for applying the techniques we've learned to both personal and professional interactions. It’s an inspiring reminder that meaningful connections are the key to success, whether in leadership, sales, or everyday life.

One of the key takeaways is the idea of creating win-win scenarios, where both parties feel valued and appreciated. By focusing on mutual benefit, Carnegie demonstrates how to foster trust, loyalty, and long-term relationships—qualities that are invaluable in both professional and personal contexts. The book also touches on subtle but impactful techniques, such as using a person’s name often, giving honest and sincere appreciation, and avoiding criticism or conflict when trying to persuade others.

These timeless principles extend far beyond the workplace, making them universally valuable for anyone seeking to enhance their communication and relationship-building skills. Whether you’re navigating business negotiations, strengthening personal relationships, or simply trying to connect better with the people around you, the lessons from this classic guide provide a roadmap for success in human interaction.


"The Slight Edge" by Jeff Olson – Olson shares the transformative power of small, consistent actions and illustrates how they compound over time to create extraordinary results. The author writes about the importance of building positive habits and making intentional choices, no matter how minor they may seem, as these decisions can significantly impact long-term success.

Much like Scott’s Master Class lesson on professional sales, this book highlights the critical role of daily discipline, perseverance, and the ongoing commitment to self-improvement. It serves as a reminder that no one reaches a high level of professional success overnight. Rather, success results from steady, focused effort over time. It's like building trust and relationships in sales. For anyone looking to master the art of starting small and staying consistent—whether in sales or life—this book can become a great supplemental guide.


"To Sell Is Human" by Daniel Pink – This book challenges traditional sales techniques by illustrating how the modern sales landscape has shifted and why traits like empathy, curiosity, and authenticity are now essential for success. Gone are the days when aggressive tactics and hard sells won over clients; today's successful salespeople understand the importance of building genuine connections. The author shows how understanding customer needs on a deeper level not only leads to better results but also fosters long-term relationships built on trust.

One of the key concepts explored is the power of curiosity and active listening. By asking the right questions and attentively hearing what a client truly wants, sales professionals can tailor solutions that feel personalized and relevant. This approach not only sets them apart from competitors but also establishes them as a trusted advisor rather than just another salesperson. The book emphasizes that sales is no longer just about moving products—it’s about solving problems and creating value, which requires a mindset shift toward understanding and collaboration.

Authenticity, another pillar of the book, is presented as non-negotiable in today's sales environment. Clients are more informed and discerning than ever, and they can easily detect insincerity. The author explains how being transparent and genuine in interactions builds credibility and fosters trust, key elements in securing both initial deals and repeat business. With practical insights and relatable anecdotes, the book provides a refreshing perspective on how empathy-driven strategies can redefine success in sales, offering valuable lessons for anyone looking to thrive in the modern marketplace.

Consider this book as another supplement to this lesson that Scott shared on professional sales.

Recap of Straight-A Guide Lessons 

• Values: Scott’s foundational value was financial stability, which he pursued through hard work and skill development.  He wanted to end the cycle of struggle and alcoholism that he saw in his parents, and defined success by becoming independent.
  
  
• Goals: He set clear, realistic goals, knowing that first he had to develop educational credentials. Although he'd been a gifted baseball player, he understood that a career in the major leagues wasn't likely, so he developed academic credentials that he believed would open new opportunities for growth. Then he applied himself, setting a series of incremental goals that put him in position to seize new opportunities, including selling to the federal government.
  
  
• Attitude: Resilience and optimism fueled his ability to handle rejection and pivot when necessary.  Scott didn't object to taking entry level jobs. He understood that a person could learn from every interaction, and he advanced his career in sales by taking roles that put him on the path to increasing levels of responsibility.
  
  
• Aspiration: During his adolescence, Scott aspired to a better life. But he didn't only dream about it. He saw himself as breaking free from a life where he couldn't pay the rent, or make a car payment. He wanted to become successful, and for that reason, when his coach told him that he could break the cycle of poverty by seeing himself in a new role, Scott took the next step.
  
  
• Action: The next step, for Scott, required action. He had to earn good grades so that he could get into college. He had to complete courses that would lead to academic credentials. Then, he had to get into the field and learn how to master the art of sales, at different levels. He was always taking action to become a master of his profession.  He even went beyond the undergraduate degree, and went on to earn a master's degree through completing night classes.
  
  
• Accountability: Commission-based pay reinforced the importance of self-accountability in his performance.  Scott understood that in sales, a person had to perform. And to perform well meant that a person had to be willing to face rejection. He mastered the numbers game, calling upon 100 people to get a single sale, or participating in a sales cycle that could take several years to complete.
  
  
• Awareness: Scott stayed informed about market trends, client needs, and new opportunities, adapting his strategies to succeed.  His willingness to attend seminars, or to read technical manuals on engineering helped him communicate more effectively with prospective customers. No one paid him to learn, yet he was willing to invest in himself, knowing it would make him more valuable to the customers who trusted him. That effort made more people aware of Scott, opening further opportunities for him to advance his career.
  
  
• Authenticity: His success stemmed from genuine connections and an unwavering focus on adding value.  He put a plan together for his life, then went through a series of priorities, checking one accomplishment off and then the next.
  
  
• Achievement: Incremental victories built his confidence, skills, and career trajectory.  Today, Scott has a sales career that delivered more than $100 million into the marketplace. But he began with an attempt to sell tickets to a comedy show. Every step was an incremental milestone.
  
  
• Appreciation: Scott acknowledged and gave back to the mentors and opportunities that shaped him.  We appreciate him for volunteering with our nonprofit, sharing his wisdom with the video lesson and the many hours he devoted to helping me craft this lesson plan.

Sample Response 

Question: What steps can you take today to build your communication and interpersonal skills? 

This response is a sample. I write as if I were still in prison, sharing what I would have learned, and how I would have used this knowledge to advance me as a candidate for a higher level of liberty, at the soonest possible time.

Response:

In listening to Scott's story, I am inspired to work harder on developing my communication skills. I'm going to begin by reading the different books that Scott recommended. 

I cannot allow the prison system to interfere with my preparations for success. Even within these restrictive walls, the power to shape my future remains firmly within my hands. I can always read, study, and grow, regardless of the circumstances. By immersing myself in books, I gain access to a vast world of knowledge and perspectives that can help me refine my understanding, sharpen my skills, and deepen my resolve.

To demonstrate my commitment to this personal growth, I will write a book report for each book I read, summarizing the key lessons and reflecting on how they will contribute to my success upon release. Through this disciplined practice, I will not only solidify my learning but also inspire others by showing the tangible progress I am making. These reports will serve as a record of my growth, a testament to my determination, and a roadmap outlining how I will transform these lessons into actionable steps toward a brighter future.

To share my book reports with a wider audience, I will publish them on the profile I build on Prison Professors Talent. This self-directed initiative will be a crucial step in improving my writing skills through consistent practice and feedback. By showcasing my reflections and growth through these reports, I aim to demonstrate my ability to extract valuable insights and effectively communicate them—skills that are highly relevant in today's marketplace.

Visitors to my profile will see not only the progress I am making but also the effort I am putting into becoming a person of value. Inspired by the strategies outlined in Scott’s master class on developing a professional sales career, I will use this platform to create opportunities, build connections, and lay the foundation for achieving long-term success.

I know many will judge me for the decades I spent in prison, but Scott gave me hope. He told me that becoming an exceptional communicator could open doors to a successful career in sales. Whether it’s selling cars or any other product, strong communication skills can lead to great earnings. More importantly, those skills can help overcome the stigma and challenges of a criminal conviction or years behind bars. Scott’s words inspired me to believe in the power of transformation through effective communication.

Challenge 

Use your profile on Prison Professors Talent to showcase how you are actively developing the skills Scott discussed. Highlight your actions and progress, showing stakeholders that you’re proactively seizing every opportunity for growth and are ready to contribute meaningfully to the workforce upon release. Explain how your work aligns with the 10 modules of the Straight-A Guide and demonstrates extraordinary potential.

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