Your cart is empty.
Keep shoppingSmart Tips: Sales, Master Relationship-Driven Selling via AI
Role Play
1,401 students
Smart Tips: Sales, Master Relationship-Driven Selling via AI
53 sales micro-lessons with AI role plays, prompts, and quizzes to build trust, win replies, and close buyer-first.
Created byCherilynn Castleman
Last updated 7/2026
English
English [Auto],
What you'll learn
- Use AI as your prep partner, practice partner, and feedback coach at every stage of the sale, with copy-and-adapt prompts in all 53 lessons
- Master relationship-driven fundamentals that never age: rapport, discovery questions, trust, follow-up, and buyer-first closing
- Practice real sales conversations in AI role plays for every section, and get coaching feedback before the stakes are real
- Build trust AI can't fake: real relationships, referrals, and social proof that make buyers answer you when they ignore automated outreach
- Research any account fast: read a 10-K with AI, build a sharp point of view, and open executive conversations with insight instead of a pitch
- Write outreach that earns replies: emails and InMails built on the 2:1 rule, timed to trigger events, and personalized in minutes with AI
- Ask questions that reveal what buyers really need, using the Four F's, the 5 Whys, and coaching frameworks like GROW
- Protect and grow your accounts: multithread your deals, re-engage at-risk clients, and time expansion so it feels like service
- Prove you can do the skill, not just describe it, with section quizzes that explain why every answer is right or wrong
Explore related topics
Course content
12 sections • 53 lectures • 2h 31m total length
Requirements
- No sales experience required. If you sell anything, a product, an idea, or yourself, you are ready to start.
- A free account with any AI chat tool (ChatGPT, Claude, Gemini, or Copilot). Every prompt in the course works with all of them.
- A willingness to practice out loud. The lessons are short. The growth happens when you use them in real conversations.
- Access to a computer or phone with internet. No fancy tech, no prior experience. Just press play and start building the skills that open doors.
Description
What separates the sales professionals who will win in 2026 from everyone else? They stopped choosing between relationships and AI. They mastered both.
And here is why that combination matters more every month. AI has flooded every inbox and every feed with outreach that sounds polished and says nothing. Buyers can no longer tell expertise from a well-prompted imitation, so they have stopped trusting polish altogether. Gartner projects that by 2028, AI agents will outnumber human sellers ten to one. In that world, the one thing AI cannot counterfeit is a real relationship: a buyer who knows you, a client who vouches for you, a track record with names attached. AI can fake expertise. It can't fake a relationship. The sellers who build both - AI fluency and genuine trust - will own the next decade of sales.
More than 1,200 sales professionals have taken this course and rated it 4.7 out of 5. Here is why it works, and why it just got a complete 2026 upgrade.
Inside, you get 53 short, focused video lessons, each one teaching a single relationship-driven sales skill you can use the same day. The videos are evergreen on purpose. Rapport, discovery questions, trust, follow-up, and buyer-first closing never go out of style. In fact, as buyers grow more skeptical of AI-generated everything, these human skills are appreciating in value. What changes fast is how you apply them, and that is where AI comes in.
Every resource around the videos has been rebuilt for 2026:
An AI Assignment for every lesson. The old tip sheets are gone. Each lesson now includes a step-by-step assignment with copy-and-adapt prompts for today's AI tools. You will use AI as a research analyst, a practice partner, a skeptical buyer, and a feedback coach, and every assignment ends with something you do in a real conversation that week.
A quiz for every section. Why? Because guessing right teaches you nothing. Every question explains why the correct answer is correct and why each wrong option falls short, so even a miss makes you sharper.
An AI role play for every section. This is the part learners tell us changes everything. You practice the full conversation with a realistic AI buyer, manager, or client who responds to what you actually say. You get coaching feedback at the end, and you can replay it until the skill feels like yours. Practice here, so you are confident when it counts.
Want a taste of what is inside? In The Most Important Document Most Sales Professionals Never Read [4 min], you will learn to pull insight from a client's 10-K and open executive conversations with a point of view instead of a pitch. Seal the Deal: 4 Buyer-First Closing Techniques [3 min] shows you how to close in a way that feels like service, not pressure. Crafting High-Impact Emails and InMails [3 min] gives you the 2:1 rule for outreach that earns replies instead of silence. Churn No More: Strategies for Retaining Customers [3 min] helps you spot at-risk accounts and re-engage them before they go quiet. And The Discovery Interview: Asking Powerful Sales Questions [3 min] teaches you to ask the questions that reveal what buyers actually need. Every lesson ends the same way: with something you do in a real conversation this week.
The 12 sections walk you through the whole arc of a relationship-driven sale: the practical fundamentals, hitting revenue targets, sales performance, customer retention, strategic alignment across your company, research and prospecting, relationship building, core techniques, personal development, advanced strategies, and where selling goes next. Start anywhere. Each section ends with a quiz and an AI role play, so you can prove the skill to yourself before you use it with a buyer.
The goal is different from most courses. Finishing a course proves you watched it. This course is built so you can do the work. Every lesson moves you from "I understand this" to "I can do this": prepare better, practice before it matters, perform when it does. AI never replaces your thinking here. It sharpens it. Your voice, your judgment, and your relationships stay yours - which is exactly why buyers will answer you when they ignore everyone else.
Starting is easy. Each video runs three to six minutes and stands on its own, so you can begin anywhere: the skill you need for tomorrow's meeting, the email that went unanswered, the account that went quiet. Five minutes between calls is enough to learn a skill. Fifteen is enough to practice it with AI. On day one, you can prep a real call, rewrite a real email, and rehearse a real conversation.
Every prompt in the course works with the free version of any major AI tool: ChatGPT, Claude, Gemini, or Copilot. If you can type a message, you can run these assignments. No technical background needed.
Who is this for? Everyone who sells, at every level. If you are new to sales, you will build the fundamentals and the AI fluency together, with no jargon and no prerequisites. If you have sold for twenty years, you will keep the instincts you have earned and add the AI edge your next decade requires. Because here is the truth about where selling is headed: everyone will learn AI. The winners will lead with it - and the winners' winners will pair it with relationships no algorithm can copy.
I have spent more than 30 years selling and coaching for Fortune 500 companies, and I now teach sales at Harvard. I built this course for busy professionals who want strategies that work now, taught fast, with zero fluff.
Join the 1,200+ professionals already selling smarter. Pick your first lesson, run your first AI assignment, and finish this week able to say the four words that matter most in sales: I can do this.
Who this course is for:
- Sales professionals who want to close bigger deals in less time, with AI handling the busywork so you can focus on the relationship
- SDRs and Account Managers building buyer trust and multithreaded relationships that survive reorgs, job changes, and the flood of AI outreach
- Sales managers and team leads who want to coach with AI role plays, section quizzes, and proven frameworks
- Entrepreneurs and founders who pitch, partner, and sell every single day
- Career changers and job seekers who need to sell their value with clarity and confidence
- Anyone brand new to sales: no jargon, no prerequisites, and every lesson stands on its own
- Experienced sellers who own the fundamentals and want the 2026 AI edge, because everyone will learn AI, and the winners will lead with it