RolePlay Mistakes

B2B deals often stall because an internal advocate cannot explain the business case to decision-makers.Biggest MistakesSellers speculate about causes instead of extracting facts, leading to incorrect assumptions.Relying on the customer to explain the value without providing a business case.Best PracticesBuild a concise documented business case: problem, importance, priority, success metrics, stakeholders, approach, investment, next steps.Collaborate with internal advocates to build the business case, making them look good and facilitating approvals.

The discussion explains that sales onboarding fails when organizations emphasize product knowledge instead of teaching a consistent, buyer-focused sales process.Biggest MistakesRelying on shadowing high performers instead of structured onboarding processes.Prioritizing product training over teaching the right questions to uncover buyer needs.Best PracticesTeach salespeople which questions reveal true buyer motivation and change catalysts.Implement a defined, repeatable sales process and indoctrinate hires into it.Provide role-play, ongoing practice, and accessible coaching when sellers get stuck.Create consistent messaging prompts to avoid adversarial language and align team communication.

Ian Altman discusses common mistakes in procurement, emphasizing the importance of not commoditizing oneself. He advises vendors to focus on what's in the customer's best interest rather than succumbing to unrealistic demands for line item pricing and cost disclosure. Altman suggests engaging with line-of-business people to understand client needs and past experiences, which can help tailor services to achieve better outcomes. He recommends shifting the focus from price to results by discussing long-term success metrics with clients. Vendors should articulate their value proposition and be prepared to negotiate based on overall solutions rather than individual items.Biggest MistakesAllowing procurement to dictate pricing and require cost disclosure, leading to commoditization.Accepting unrealistic procurement demands without proposing a results-focused alternative.Best PracticesEngage line-of-business stakeholders early to ensure the solution improves outcomes.Ask and agree on measurable success metrics before selling or delivering.Offer bundled pricing tied to accountability to emphasize solution over line items.Present your success formula and collaboratively adapt it to the client's buying rules.

Ian Altman discusses why demos in B2B sales often fail to generate revenue despite positive feedback. He argues that reps too often focus on the demo as the goal, neglecting the importance of understanding the client's problem and business case. Altman suggests that sellers should first ensure the client has a problem worth solving and that the seller can deliver the desired outcome. He advises tailoring demos to show only the necessary features that address the client's specific needs, rather than overwhelming them with every capability. This approach aligns the demo with the client's definition of success and increases the likelihood of closing a deal.Biggest MistakesTreating the demo itself as the primary sales goal.Showing every product feature and overwhelming prospects.Best PracticesConfirm client has a problem worth solving before discussing product.Use benchmarked examples to help clients estimate costs.Co‑define success metrics and ask client what they must see.Demo only the agreed three or four capabilities tied to outcomes.

Ian Altman discusses why sellers struggle to close deals, emphasizing that the key to success is building trust and focusing on the client's outcome from the initial meeting. He highlights three common buyer concerns: trust, problem severity, and better alternatives. Altman advises sellers to "disarm" clients by showing genuine concern for their results rather than just making a sale. He suggests asking questions about success metrics and potential obstacles, which few vendors do. This approach, known as same-side selling, can lead to faster sales, less price sensitivity, and more repeat business if executed effectively.Biggest MistakesOffering discounts or creating false urgency heightens buyer concern and appears desperate.Asking transactional questions like decision makers and contract mechanics instead of outcome questions.Using the term "closing" instead of framing sales as opening a relationship.Best PracticesDisarm by making the client's outcome more important than the sale.Early in process, define success metrics to measure outcomes together.Ask about potential obstacles to achieving results to build shared focus.Reinforce trust and confidence throughout the sales process so clients see outcome focus.Delivering results drives repeat and referral business.

Ian Altman discusses common blind spots in the use of AI in B2B sales, emphasizing the importance of avoiding proprietary information leakage through tools like ChatGPT and Copilot. He highlights issues with using general-purpose AI for specific sales questions and the potential for AI models trained on Reddit discussions to provide unreliable answers. Altman promotes the Same Side Selling Academy's AI tool, the Same Side Coach, which is tailored to sales strategies and protects intellectual property. He encourages the use of AI for general tasks but advises using specialized tools for specific sales applications to prevent competitors from accessing valuable information.Biggest MistakesAsking detailed proprietary questions in public AI tools, exposing informationAsking general-purpose AI very specific strategic sales questions, getting generic answersCopying and pasting AI responses without reviewing or modifying themBest PracticesProtect intellectual property; avoid feeding proprietary data into broad AI systemsUse AI for transcription, note-taking, and meeting summaries as appropriateUse a domain-tuned LLM (Same Side Coach) trained on sales-specific data

Ian Altman discusses the common trap of assuming a client's initial request for a product is accurate. He emphasizes that clients often need something different than what they initially think. Altman advises salespeople to ask probing questions to understand the client's actual needs and problems. This approach helps build a stronger business case and ensures the product or service provided solves the client's underlying issues. He suggests questions like "What are you trying to solve?" and "What happens if you don't solve this?" to uncover the client's true requirements. This method aligns the salesperson with the client, enhancing the likelihood of a successful sale and long-term satisfaction.Biggest MistakesJumping to the solution without diagnosing the problem first.Providing basic pricing and ordering info prematurely when prospect is excited.Following up without meaningful context, resulting in weak outreach.Best PracticesSlow down to speed up: diagnose before proposing solutions.Focus on outcomes over the sale to ensure the right solution.Build the client's business case: define problem, impact, and measurable outcomes.Engage relevant stakeholders, including end users, to confirm requirements.

Ian Altman discusses common mistakes in procurement, emphasizing the importance of not commoditizing oneself. He advises vendors to focus on what's in the customer's best interest rather than succumbing to unrealistic demands for line item pricing and cost disclosure. Altman suggests engaging with line-of-business people to understand client needs and past experiences, which can help tailor services to achieve better outcomes. He recommends shifting the focus from price to results by discussing long-term success metrics with clients. Vendors should articulate their value proposition and be prepared to negotiate based on overall solutions rather than individual items.Biggest MistakesAllowing procurement to dictate pricing and require cost disclosure, leading to commoditization.Accepting unrealistic procurement demands without proposing a results-focused alternative.Best PracticesEngage line-of-business stakeholders early to ensure the solution improves outcomes.Ask and agree on measurable success metrics before selling or delivering.Offer bundled pricing tied to accountability to emphasize solution over line items.Present your success formula and collaboratively adapt it to the client's buying rules.

Ian Altman discusses the importance of role play in sales, emphasizing that top performers practice more than they perform. He identifies three common mistakes: not role playing at all, lacking structure in role play sessions, and providing overwhelming feedback. Altman suggests a structured approach with three roles: salesperson, customer, and observer, using secret cards to introduce variability. Each 10-minute role play session involves feedback from all three roles, focusing on one key improvement area. This method, practiced consistently, can significantly enhance sales skills and confidence.

Ian Altman hosts the Same Side Selling Podcast featuring SolarInsure, highlighting their success with the same side selling methodology. SolarInsure helps contractors overcome consumer skepticism and profitability issues by offering a 30-year transferable warranty backed by Zurich North America. Despite industry challenges, including tariffs and policy changes, SolarInsure doubled their business in 18 months. Their strategy involves becoming trusted advisors, identifying mutual fit, and focusing on operational excellence. They emphasize consistent execution, role-playing, and maintaining a playbook. SolarInsure's growth is attributed to their commitment to solving customer problems and fostering a culture of efficiency and collaboration.