Insight Selling

Why do some salespeople consistently win while others—seemingly just as qualified—come in second place? In Insight Selling, Mike Schultz and John E. Doerr tackle this mystery head-on. Drawing from their RAIN Group research on over 700 major B2B purchases, they reveal that sales winners aren’t just better at pitching products—they sell differently. They bring insight to the table. These sellers educate buyers with new ideas, collaborate to co-create solutions, and inspire action by reframing how buyers think about problems and possibilities.

The authors contend that today’s most successful sellers operate in a radically changed environment. Buyers are flooded with information, have access to endless options, and approach purchasing with skepticism. Solution and consultative selling—once dominant methods—are no longer sufficient. The “value” used to reside in the product or service. Now, in a world of commoditization and parity, the seller has become the value. Schultz and Doerr argue that selling has evolved into an intellectual and creative pursuit: winning sales requires leading the buyer with insight, not following with features.

The Core Framework: 3 Levels of RAIN Selling

The book’s backbone is the RAIN Group’s “3 Levels of RAIN Selling” model—Connect, Convince, Collaborate. These levels emerged from the study comparing winners to second-place finishers. Winners excelled not simply by having strong products, but by mastering all three levels simultaneously:

• Connect: They connect the dots between buyer needs and solutions—and connect personally with buyers through empathy, trust, and authenticity.
• Convince: They persuade buyers that the return is worthwhile, the risk is acceptable, and they themselves are the best choice.
• Collaborate: They work with buyers as partners, not participants—co-creating solutions and ideas to achieve shared goals.

This trifecta demonstrates how insight permeates every level of the sales process. Connection builds trust, conviction reduces risk, and collaboration transfers ownership of ideas from seller to buyer. The result? Buyers not only purchase more confidently—they stay loyal longer.

From Product Value to Seller Value

The authors present a compelling argument: in most industries, products and services have become interchangeable. Buyers no longer differentiate based on what they buy, but whom they buy from. As Schultz and Doerr put it, “In a sea of perceived sameness, the sellers themselves are the difference.” This insight selling revolution marks a profound shift—sellers must now help customers see and act on opportunities they didn’t even know existed. The seller transforms from vendor to change agent.

This leads to their twin concepts: Opportunity Insight and Interaction Insight. Opportunity insight means educating the buyer about new ways to think and new strategies to pursue. Interaction insight means co-creating ideas through conversation. Exceptional sellers blend both. When buyers say “They helped me see possibilities I didn’t realize,” that’s opportunity insight at work. When they say “They challenged how we think about this problem,” that’s interaction insight.

Cognitive Reframing and Change Agency

Behind every act of insight lies cognitive reframing—the ability to help buyers see problems, strategies, or opportunities differently. Schultz and Doerr redefine the seller as a change agent. Sellers must lead buyers out of their comfort zones by providing perspectives that alter how they view truth and possibility. “Difference means change,” the authors assert; sellers who fail to provoke change simply remain part of the status quo.

This principle mirrors ideas from The Challenger Sale by Matthew Dixon and Brent Adamson, but Schultz and Doerr emphasize a key distinction: challenging the buyer must serve the buyer’s best interest, not the seller’s ego. Insight selling isn’t about provocation for provocation’s sake—it’s about collaboration that creates mutual success. Sellers who push too far become arrogant; those who push too little fade into irrelevance.

Why Insight Matters Now

Buyers may enter the sales process informed, but they’re often overwhelmed by options and conflicting data. Schultz and Doerr reference Barry Schwartz’s The Paradox of Choice: more information doesn’t produce better decisions—it drives paralysis. Insight restores confidence. Buyers crave understanding, not just information. When a seller educates, collaborates, and convinces with insight, they become indispensable guides through complexity—a trusted advisor rather than a transactional vendor.

Ultimately, Schultz and Doerr’s message is one of transformation. You can’t just sell products anymore—you must sell ideas that matter. By embodying the RAIN framework and leading with insight, you become what every modern buyer really wants: a partner who helps them win. The book promises more than techniques—it offers a mindset shift from selling solutions to selling change itself.

Winners combine rational resonance (ROI) with emotional resonance (empathy, validation). Buyers buy with their hearts and justify with their heads. Relationship sells first, insight follows.

Ask Better Questions to Create Insight

Inquiry is as vital as advocacy. Great questions demonstrate competence and push buyers into the learning zone. The University of Memphis study cited by the authors found that knowledgeable people ask “why,” “what if,” and “how” questions—precisely the disruptive inquiry needed to unlock insight. Schultz suggests eleven types of disruptive questions that challenge assumptions and spark cognitive reframing, such as “What will happen if you don’t act?” or “Why did you settle on this strategy?”

From Rapport to Partnership

Once buyers trust your expertise and character, relationship strength grows into partnership. The authors provide a diagnostic grid—from “transactional” to “essential”—for sellers to assess relationship depth. At the highest level, buyers say: “Losing this provider would be catastrophic.” To reach that tier, you must make yourself indispensable through empathy, insight, and trust-based influence. (Compare with Charles Green’s The Trusted Advisor, where trust is built through credibility, reliability, and intimacy.)

After connection comes conviction—the ability to make buyers believe in change. Sellers must help buyers see why an idea is worthwhile, minimize perceived risk, and build emotional commitment. Schultz and Doerr devote an entire chapter to storytelling as the key persuasive tool.

Storytelling as Cognitive Transport

A powerful story moves people. Neuroscientific studies show that listeners’ brain patterns synchronize with storytellers’, a process called neural coupling. The authors use this as proof that storytelling triggers both emotion and understanding. Jeff Park of Catamaran notes that sellers who say “Have you ever thought about...” followed by a client story earn his attention. Stories create empathy and serve as proof points for insight.

The Convincing Story Framework

Schultz’s seven-part storytelling structure offers a roadmap for persuasion: Connection, Dissatisfaction, Desire, Dissatisfaction Layering, Breakthrough, Results, Action. Each stage builds belief.

• Start with Connection—show you understand the buyer’s world.
• Then amplify Dissatisfaction—make the status quo painful to maintain.
• Show a clear Desire—paint a vision of an attractive future (the 'new reality').
• Layer dissatisfaction and reveal obstacles so buyers feel the need for change.
• Provide a Breakthrough—your insight or new idea that resolves despair.
• Present Results—credible ROI evidence and emotional satisfaction.
• End with Action—invite collaboration, not just a purchase.

Fear of Loss and Risk Reduction

Borrowing from behavioral economics, Schultz emphasizes loss aversion: buyers are motivated more by avoiding pain than pursuing gain. Sellers must spotlight what happens if nothing changes—the danger of stagnation. They also must minimize perceived risk in four areas: the seller, the offering, the company, and the outcome. When buyers trust all four dimensions, belief becomes action. (Compare to Daniel Kahneman’s notion that “losses loom larger than gains.”)

A Personal Metaphor: Buying Heart Surgery

In a deeply human analogy, Schultz recounts choosing a groundbreaking fetal heart surgery for his son. He applies the same resonate-differentiate-substantiate model: he wanted the surgery (resonate), trusted Boston Children’s Hospital as the best option (differentiate), and believed the surgeons could deliver (substantiate). The story illustrates that even life-and-death decisions follow emotional resonance, rational justification, and trust—the same principles governing complex business buys.

In the third level—Collaborate—buyers and sellers become partners in success. Schultz and Doerr discovered that the top two factors distinguishing winners from second-place finishers were “educated me with new ideas or perspectives” and “collaborated with me.” Collaboration transforms selling from persuasion into shared creation.

Collaboration as a Human Drive

Drawing on Kurt Lewin’s classic psychology experiments, the authors show that involvement beats persuasion. Homemakers who participated in group discussions were ten times more likely to serve new foods to their families than those lectured to. Similarly, buyers act on ideas they help shape. Collaboration builds “psychological ownership”—the buyer feels the idea is theirs.

The PATHS to Action Framework

To make collaboration systematic, RAIN Group developed PATHS to Action: Premise, Assumptions, Truths, Hypotheses, Solutions. Sellers use this five-step facilitation method to run effective meetings:

• Premise: Define the reason for meeting—problem, opportunity, or paralysis.
• Assumptions: Explore beliefs and perspectives around the situation.
• Truths: Filter assumptions to uncover verified facts.
• Hypotheses: Generate and evaluate possible paths forward.
• Solutions: Co-create an actionable plan with buyer commitment.

This process turns selling into leadership. The seller becomes the facilitator of breakthroughs, not just a messenger of features.

Desire and Ownership

Psychological ownership changes the game. When buyers help shape the idea, it becomes part of their agenda. Schultz notes that collaboration works equally well when sellers drive demand (“You should consider this new approach”) and when buyers drive demand (“We need help achieving our goal”). Either way, involvement deepens trust and accelerates decisions.

As Jeff Park of Catamaran said, “You’re on display at every opportunity. Through a nine-month process, collaboration proved we were the right choice—it was something they could feel.” In short, collaboration converts intellectual alignment into emotional commitment.

Trust underpins every level of insight selling. Schultz and Doerr describe trust as the foundation upon which risk-taking and change become possible. Buyers only follow advice to the extent they trust the seller.

Three Components of Trust

• Competence: Buyers must believe the seller can deliver. Knowledge, preparation, and business acumen are key signals. Bright Horizons CEO David Lissy expects sellers to understand his business model deeply before proposing solutions.
• Integrity: Buyers trust sellers who act in their best interest—even recommending competitors if necessary. Beneficial Bank’s Gerry Cuddy recounts turning away a profitable deal because it wasn’t right for the client, earning lasting loyalty.
• Intimacy: The depth of personal connection that enables candid conversations. Genuine rapport and shared experience transform professional relationships into enduring partnerships.

Earning Time with Executives

High-level clients don’t lack time—they lack trust in who deserves it. Schultz outlines how to earn access: establish peer-level presence (gravitas), get over self-doubt, jump the impact hurdle (discuss big ROI topics), and engage personally. Executives ultimately invest their time in people who bring both insight and authenticity. (Compare with Patrick Lencioni’s notion in Getting Naked that vulnerability earns client confidence.)

Trust transforms advice into influence. A buyer may resist an idea from a stranger but welcome the same counsel from a trusted advisor. Developing trust takes time—but once earned, it makes selling effortless. As Schultz concludes, “Selling is insight; insight requires trust.”

Becoming an insight seller isn’t just about learning techniques—it’s about developing the right attributes. Schultz and Doerr identify the inner qualities that differentiate true change agents from average performers. The best sellers don’t just know what to do—they want to do it and will do it consistently.

Tendencies: What Drives Action

• Passion for Work and Selling: Without genuine enthusiasm, effort becomes compliance instead of commitment.
• Conceptual Thinking: The ability to see patterns and design innovative strategies.
• Curiosity: Drives deep discovery and lifelong learning—essential for insight.
• Sense of Urgency: Avoids the “law of diminishing intent,” moving action forward before momentum fades.
• Assertiveness: Courage to challenge thinking and stand by convictions.
• Money and Performance Orientation: Align motivation with results.

Qualities: How Action Is Executed

• Gravitas: Substantive presence and credibility that commands respect.
• Business Acumen: Understanding how decisions impact the buyer’s success.
• Perseverance: Commitment to long-term success in complex sales environments.
• Integrity and Emotional Intelligence: Balances assertiveness with empathy to maintain trust and composure under pressure.

Schultz warns that arrogance and meekness are twin traps. Insight requires confidence balanced by humility and compassion. Emotional intelligence ensures you challenge constructively, not combatively. (Similar to Daniel Goleman’s findings in Emotional Intelligence that empathy and self-regulation determine professional success.)

Insight selling demands sellers who think like educators, act like consultants, and lead like visionaries. As Leonard Schlesinger of Harvard sums up, “The meat isn’t being nice—it’s being systematically knowledgeable.”

Not all buyers are ready for insight. Schultz and Doerr categorize buyers into two buying modes and six personas, helping sellers tailor their approach.

Two Buying Modes

• Problem-Solving: Buyers seek fixes for underperformance. They’re open to change but focused on eliminating pain points.
• Future-Seeking: Buyers want growth and innovation. They invest to reach ambitious goals.

Non-buying modes include satisfied and euphoric states—where inertia or success prevents action. Sellers should prioritize problem-solving and future-seeking buyers who “want to change.”

Six Buyer Personas

• Decisive Danielle: Direct, assertive, results-driven. Loves bold ideas—show ROI clearly.
• Consensus Claire: Collaborative and cautious. Requires alignment and diplomacy—facilitate group agreement.
• Relationship Renee: Warm and enthusiastic. Values connection—harness her energy as a champion.
• Skeptical Steve: Reserved realist. Provide evidence, not hype—slow trust builder but steady supporter.
• Analytical Al: Data-driven perfectionist. Needs abundant proof—insight selling demands patience here.
• Innovator Irene: Creative maverick. Loves testing boundaries—ideal buyer for opportunity insight.

Understanding who’s in the room—and what drives them—prevents misfires. A Decisive Danielle may thrive on challenge, while a Consensus Claire views it as confrontation. Schultz advises sellers to “read the room and calibrate their provocativeness throttle.” In essence, know who wants bold change and who needs gentle guidance.

Insight selling succeeds when sellers match their style to both buying mode and persona. A future-seeking Innovator Irene, for instance, will embrace radical ideas, while a satisfied Analytical Al will resist even minor change. Tailoring insight to buyer psychology turns understanding into conversion.

Schultz and Doerr conclude with a practical roadmap for organizations. Developing insight sellers isn’t a one-off event—it’s a cultural pursuit. Too many companies run short sales workshops that entertain but fail to transform. Real growth requires alignment, fluency, assessment, process, engagement, reinforcement, and evaluation.

The Seven Failures of Sales Training

• Failing to align goals with training needs—wishful thinking replaces real planning.
• Ignoring sales knowledge fluency—accuracy without speed and depth leads to paralysis.
• Overlooking attributes—skills can be taught, mindsets must be chosen.
• Neglecting process and methodology—training must sync with systems like CRM.
• Delivering boring events—without engagement, nothing sticks.
• Skipping reinforcement—learning fades after 120 days unless sustained.
• Lacking evaluation and accountability—without metrics, improvement stalls.

The authors urge firms to treat training like health care, not entertainment: maintain diagnosis, treatment, and follow-up, not just motivational injections. Reinforcement, coaching, and continuous improvement ensure change persists. They cite Aberdeen’s data: best-in-class organizations invest twice as much in training and see 80% of reps hitting quota versus only 6% among laggards.

Building Insight Culture

Effective organizations combine capability (skills and knowledge) + attributes (motivation and mindset) + action (clear processes and goals) + evaluation (feedback loops). When these align, sellers can do, will do, know what to do—and keep getting better. Insight selling becomes more than a technique—it becomes organizational DNA.

Final Metaphor: Building a Cathedral

In the epilogue, Schultz compares the journey to constructing a cathedral, brick by brick. Selling made simple, he says, doesn’t exist—like mastering guitar or neurosurgery, excellence takes time, focus, and discipline. Products may be interchangeable, but people never will be. The insight seller isn’t building a wall; they’re building an enduring masterpiece of trust and value.