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, 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 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 and Donald C. Kelly on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom.