Stop Teaching AI Tools...Do This Instead! | Cherilynn Castleman - 26

Before You Can Sell, You Must Know Yourself | Cheryl Parks - 29

What if success in sales starts long before your first prospect call? Before mastering sales techniques, Cheryl Parks believes professionals must first understand who they are. She joins us to explore how self-awareness, personal strengths, and identity influence long-term success in sales. Meet Cheryl Parks * Cheryl Parks is a revenue growth advisor, sales leader, and strategic operator who helps founders, executives, and sales teams navigate growth with greater clarity, confidence, and execution. With more than 30 years of experience in B2B enterprise sales, she has sold over $25 million into Fortune 1000 organizations and coached leaders to achieve multi-million-dollar outcomes. * Known for her journey from "the shyest girl in the room" to trusted advisor, Cheryl brings a practical, human-centered approach to sales and leadership. She helps organizations identify revenue opportunities, align teams, improve decision-making, and build scalable sales systems without sacrificing trust or connection. * As Chief Revenue Officer at Digital Factory and founder of The Sales Growth Advisor, Cheryl works at the intersection of revenue strategy, leadership alignment, and AI-powered business transformation. She views AI as a tool that enhances human judgment, focus, and performance rather than replacing authentic leadership. * Today, Cheryl speaks on sales, leadership, AI adoption, and revenue growth, helping professionals build sustainable, high-trust approaches to success in a rapidly changing business landscape. Sales Success Starts with Self-Awareness * Cheryl shares practical ways students and new sales professionals can identify their strengths, personality traits, and selling style. From relationship-focused sellers to transactional sales experts, she explains why there is no single path to success in sales. * We also explored how tools such as CliftonStrengths, DISC, Enneagram, Myers-Briggs, and even AI can help individuals better understand where they fit within the sales profession. Developing the Seller You Want to Become * One of Cheryl's most powerful messages is the importance of intentionally creating your future identity. Instead of "fake it until you make it," she advocates for acting like the person you aspire to become while remaining authentic. * She also discusses the value of mentors, personal mantras, continuous learning, and surrounding yourself with positive influences that support your growth. Navigating Setbacks and Growth * Sales careers come with challenges, rejection, and periods of self-doubt. Cheryl offers practical advice for evaluating setbacks, assessing your skills and motivation, and identifying when it's time to pivot, improve, or set new goals. "Sales completely changed my life, literally. It helped me move forward and grow." — Cheryl Parks Resources * Professors interested in curriculum, simulations, lesson plans, and sales education tools can explore Stukent Sales Courseware [https://www.stukent.com/?utm]. Interested in developing your sales skills or growing your business? Reach out to Cheryl Parks and connect with her on LinkedIn [https://www.linkedin.com/in/growth-revenue-ai/] for practical advice on sales, leadership, and personal growth.

What Is The Shadow Discovery Meeting & How You Should Teach It? | Donald C. Kelly & Dr. BJ Allen - 28

Salesforce found that 80% of customers feel salespeople don’t bring enough value to the buying process. At the same time, most sellers think the deal keeps moving forward once the discovery call ends. What many fail to realize is that the real conversations are often happening behind the scenes. That’s why Dr. BJ Allen and I are breaking down the concept of the “shadow discovery” and how professors can better prepare students for the realities of modern enterprise selling. The Reality of Modern Buying Committees * Enterprise selling has become far more complex than it used to be. Buying committees now often involve 8 to 11 stakeholders, and not every influential voice is officially part of the decision-making team. * We also explain how buyers are doing more independent research before ever speaking with salespeople. Between AI tools, online reviews, and peer recommendations, many prospects already have strong opinions before the first sales conversation even happens. What Is A Shadow Discovery? * A shadow discovery is the internal conversation prospects have when the salesperson is no longer in the room. * These conversations can happen in meetings, Slack messages, Teams chats, or side conversations between executives after a discovery call. One negative opinion or unanswered concern during those moments can quickly stall a deal. * Dr. Allen explains why students need to understand that selling is no longer just about the conversation happening directly with the prospect. It’s also about preparing for the conversations happening behind closed doors. How To Better Prepare Students For Enterprise Selling * We also share strategies professors can teach students to help them navigate modern buying committees more effectively. * This includes identifying true internal champions, creating tailored content for different stakeholders, using business acumen to align with executive priorities, and helping champions confidently communicate value internally. * Role plays and real-world sales scenarios can also help students better understand how multi-threading and internal selling actually work during complex deals. “Shadow discoveries are happening. It's a constant piece of the conversation and we need to make sure we're ready for it.” — Donald C. Kelly “Shadow discoveries influence purchasing decisions, and they’re problematic because the salesperson isn’t there.” — Dr. BJ Allen Resources Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom.

Before You Teach Sales This Semester, Listen to This | Donald C. Kelly & Dr. BJ Allen - 27

What actually makes a sales class effective? Is it the lectures, the role plays, the assignments, or the real-world experience students walk away with? We’re breaking down how sales professors can better prepare for the next semester by creating a more practical and engaging learning experience for students. We also share how professors can better understand which lessons actually prepare students for real sales roles. Why Student Feedback Matters More Than You Think * One strategy you can try is giving students an assignment at the end of every semester where they explain the four most important things they learned in class and how they plan to apply those lessons in their careers. * That feedback can help identify which concepts students actually find useful in the real world and which topics may need to be adjusted or removed. * Dr. Allen also shares how often students mentioned time management and planning as lessons that had a major impact on them. * While it may not seem like the most exciting topic, students repeatedly shared how helpful those planning strategies became in preparing them for real sales roles. Building a More Practical Sales Classroom * We also share some of the challenges professors face when trying to balance academic concepts with practical sales training. * Using role plays, prospecting exercises, and LinkedIn outreach activities can give students hands-on experience and help them better understand how sales actually works outside the classroom. * Creating an effective sales class also means reducing the workload for professors while still giving students a personalized learning experience. * Lesson plans, activity banks, simulations, grading tools, and role play exercises can make a major difference for professors teaching sales for the first time. How AI Is Changing Sales Education * Dr. Allen explains how AI role play tools now allow students to practice discovery calls, receive instant feedback, and improve their skills in a low-pressure environment. * Instead of relying only on live role plays or manual grading, AI simulations can create more consistency, repetition, and flexibility for both students and professors. “There’s nothing like having students tell you what they actually found useful for their career.” — Dr. BJ Allen “Hands-on activities help students better understand how sales actually works outside the classroom.” — Donald C. Kelly Resources * Professors interested in curriculum, simulations, lesson plans, and sales education tools can explore Stukent Sales Courseware [https://www.stukent.com/?utm]. * Interested in bringing AI role plays and sales simulations into your classroom? Try Copient AI [https://www.copient.ai/?utm]. * For additional sales education content, listen to The Sales Evangelist [https://thesalesevangelist.com/?utm]. Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom.

Stop Teaching AI Tools...Do This Instead! | Cherilynn Castleman - 26

How do you teach students to actually use AI effectively instead of just relying on random tools and prompts? We invited Cherilynn Castleman, a sales consultant and professor at Harvard University, to discuss how AI is reshaping sales education. She explains why professors should focus less on specific platforms and more on helping students develop true AI fluency. Meet Cherilynn Castleman * Cherilynn Castleman is a sales consultant, AI strategist, and professor at Harvard University, where she teaches courses focused on AI adoption and AI fluency in sales. * She helps sales professionals and organizations understand how to integrate AI into modern sales workflows while still building authentic human connection. * Through her teaching, consulting, and content, Cherilynn focuses on helping people move beyond simply using AI tools and instead develop the confidence and clarity needed to succeed in an AI-driven sales environment. Why AI Fluency Matters More Than Learning Tools * One of the biggest points Cherilynn shares is how quickly AI tools are changing. She explains that between 50 to 100 new AI sales tools are entering the market every single week. That means professors cannot realistically keep up by teaching tools alone. * Instead, students need to understand how to think with AI, communicate with it effectively, and integrate it into their sales workflow. * Cherilynn compares AI fluency to learning a second language. At first, it feels uncomfortable, but over time students develop confidence and clarity in how to use it naturally. Why Companies Are Struggling With AI * Even though companies are heavily investing in AI, many are still not seeing results. * Cherilynn shares that global AI spending is projected to reach $2.5 trillion in 2026, growing 44% year over year. Yet according to MIT research [https://www.forbes.com/sites/andreahill/2025/08/21/why-95-of-ai-pilots-fail-and-what-business-leaders-should-do-instead/?utm], 95% of organizations report seeing little to no ROI from their AI implementation. * The reason? Most companies are focused on tools instead of teaching people how to actually use AI strategically. How AI Can Make Students Better Sellers * One of the most interesting parts of the conversation focused on how AI can help students become stronger communicators and better sales professionals. * Cherilynn explains how students can use AI to: * personalize outreach faster * improve discovery questions * research prospects and industries * create stronger points of view * identify weaknesses in their sales process * Instead of replacing sellers, AI helps elevate them. Teaching Students to Build Better Buyer Relationships * Cherilynn also shares how AI can help students create stronger emotional connections with buyers by improving the quality of their discovery questions. * She explains that 87% of B2B buyers want sales professionals to show up as trusted advisors. * AI can help students prepare better questions, understand customer challenges, and communicate more strategically during conversations. “AI can help you build trust by improving the questions you ask and strengthening your connection with buyers. Develop a POV because your point of view is how you show up.” — Cherilynn Castleman Resources Want to learn more about AI fluency and the future of sales education? Connect with Cherilynn Castleman on LinkedIn [https://www.linkedin.com/in/cherilynn-castleman/] and follow her insights on how AI is reshaping the way sales professionals learn, sell, and build stronger customer relationships. Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom.

The Best Way To Utilize AI In Your Sales Class | Donald C. Kelly & Dr. BJ Allen - 25

Over the last few years, AI has made its way into everything. So how do you actually bring it into your sales classroom in a way that prepares students for the real world? We partnered with Stukent to show you how to use it for roleplay in the classroom. Why AI Is Changing Sales Education * AI is not just a trend. It is already shaping how sales professionals work every day. The challenge for professors is figuring out how to bring that into the classroom in a way that feels practical and relevant. * This is where AI roleplay comes in. Instead of relying only on student to student practice, professors can now create more realistic selling environments. Making Roleplay Feel Real * One of the biggest challenges in teaching sales is making roleplay feel authentic. Students know when it is just practice. * With AI, that changes. The buyer responds in real time, asks questions, and even pushes back like a real prospect would. * That means students are not just memorizing scripts. They are learning how to think, adapt, and respond in the moment. Better Experience for Students and Professors * AI roleplay does not just help students. It also makes things easier for professors. * Instead of reviewing every interaction, AI can handle feedback and evaluation, reducing workload while still giving students a high quality experience. * It also removes bias and creates a more consistent learning environment. Preparing Students for the Real World * The goal is simple. Help students feel what real selling is like before they step into their first role. * With AI, you can adjust difficulty levels, simulate different buyer personalities, and create scenarios that reflect real sales conversations. “One of the best things about AI roleplay is you can adjust the difficulty. For beginners, it can be simple, but at advanced levels, it feels real. I’ve seen it hang up on students within 20 seconds, just like real life.” — Dr. BJ Allen Resources Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom. Learn how you can bring AI into your classroom and more about Stukent here [https://www.stukent.com/].