The Challenger Sale

Reverse-engineer a Commercial Insight from seller strengths and validate it against the four-criteria test. Trigger this skill when you need to: - Build a commercial insight or reframe for a teaching pitch - Figure out "what insight should I teach" in a B2B sales conversation - Find a unique angle for a commercial teaching pitch - Reverse engineer a pitch from your strengths (the "Deb Oler question") - Identify which insight to lead with in an insight-led selling approach - Differentiate your pitch from competitors who sell the same category - Determine whether a proposed reframe qualifies as commercial teaching - Start a sales narrative from your solution's unique differentiator rather than customer pain - Create an insight that "leads to" your strengths rather than "leading with" them NOT for: building the full 6-step pitch choreography (use author-commercial-teaching-pitch), tailoring to specific stakeholders (use tailor-pitch-by-stakeholder), or scoring pitch boldness (use SAFE-BOLD framework).

Tailor a Commercial Teaching pitch to each stakeholder role using Functional Bias Cards and route the pitch to avoid the C-suite elevation trap. Trigger this skill when you need to: - Tailor a sales pitch to different roles in a buying committee - Build stakeholder-specific messaging for a multi-stakeholder sale - Create a different message for VP Engineering vs CFO vs procurement - Use a Functional Bias Card to map what each role cares about - Build a stakeholder map for an enterprise deal - Understand who to pitch to first and in what order - Adapt a pitch for different audience roles without losing the core insight - Tailor for resonance with a buying committee - Create per-role pitch variants from a single base pitch script - Build consensus across a buying group before reaching the decision-maker NOT for: building the base pitch (use author-commercial-teaching-pitch first), building the underlying commercial insight (use build-commercial-insight), or diagnosing an existing pitch's structure (use diagnose

Diagnose a deal's taking-control posture: foil-RFP detection, passive/assertive/aggressive positioning, and misconception analysis. Trigger this skill when you need to: - Diagnose a stalled deal to find out why it isn't moving - Determine whether you're in a foil RFP (a verification exercise, not a real opportunity) - Assess whether a rep is too passive, appropriately assertive, or crossing into aggressive territory - Identify misconceptions about "taking control" that are limiting a rep's deal behavior - Understand why you're losing control of the sale or the customer conversation - Apply constructive tension without becoming combative - Evaluate whether a customer is verifying price with a competitor already chosen - Unblock a stalled pipeline deal by diagnosing the control gap - Coach a rep who is too passive or who conflates assertiveness with aggressiveness - Determine whether a rep is helping the customer navigate their own buying process (Lead and Simplify) NOT for: full negotiation planning — concessi

Plan a full Challenger model rollout for a sales organization. Use when someone asks: 'implement Challenger model', 'roll out new sales methodology', 'sales transformation plan', 'change management sales', 'pilot Challenger', 'sales methodology adoption', 'implementation roadmap', 'enablement plan', 'sales training rollout', 'sales change management', 'how do I roll out Challenger', 'Challenger implementation plan', 'sales force transformation', 'how to scale Challenger across the team'. Applies Grainger's four-question pilot framework, star/core/laggard adoption sequencing, 80% adoption target, 20–30% attrition planning, and a four-track parallel workstream design (training, tools, coaching, manager enablement). Produces a rollout-plan.md with pilot scope, adoption sequence, 12-month milestone schedule, and attrition/backfill plan.

Plan a structured coaching session for a sales rep using the PAUSE framework (Prepare → Affirm → Understand → Specify → Embed). Use when a manager needs to: run a 'sales coaching session', 'coach a sales rep', use 'PAUSE coaching', ask 'pre-call coaching questions', run a 'post-call debrief', do 'challenger rep coaching', follow a 'sales manager coaching guide', 'coach the rep not the deal', answer 'how to coach my rep', or build a '1:1 coaching agenda'. Reads rep-profile-assessment.md from classify-rep-profile to identify the rep's weakest Challenger pillar, selects the Appendix A question set for that pillar, and produces a coaching-session-plan.md with pre-call questions, observation focus, post-call debrief, and an embed homework assignment. Also includes a decision gate: if the issue is deal-specific (stalled deal, unknown obstacle) rather than a rep-behavior gap, routes to the sales innovation mode (Investigate → Create → Share + optional SCAMMPERR) instead of PAUSE coaching.

Diagnose a frontline sales manager's effectiveness against the CEB four-driver model. Use when someone asks: 'sales manager effectiveness', 'am I coaching the right reps', 'sales manager diagnostic', 'manager coaching ROI', 'where should I spend coaching time', 'sales manager assessment', 'Challenger sales manager', 'manager drivers', 'front-line manager performance', 'am I a good sales manager', 'sales manager self-assessment', 'coaching time allocation', 'am I spending coaching time correctly', 'democratic coaching', 'why is my team not improving'. Produces a manager-effectiveness-diagnosis.md with weighted driver scores, active anti-patterns, and a concrete time-reallocation plan based on team composition.

Author a Commercial Teaching pitch using the six-step choreography and polish it with SAFE-BOLD. Trigger this skill when you need to: - Write a sales pitch using commercial teaching methodology - Build a commercial teaching pitch from a validated insight - Structure a six-step pitch: warmer reframe rational drowning emotional impact new way solution - Author a sales narrative that leads to your solution rather than leading with it - Build a sales deck following challenger selling choreography - Write a challenger pitch or insight-led pitch for a B2B conversation - Draft a pitch script for a sales rep or sales enablement team - Differentiate a sales conversation by teaching customers something new about their business - Apply SAFE-BOLD to sharpen a teaching pitch before delivery NOT for: building the commercial insight itself (use build-commercial-insight first), tailoring the pitch to individual stakeholders (use tailor-pitch-by-stakeholder after), or diagnosing an existing pitch (use diagnose-pitch-for-comme

Build a pre-call negotiation plan using DuPont's four-step framework and sequence concessions to avoid the proactive-discount and ultimatum traps. Trigger this skill when you need to: - Plan a negotiation for a B2B sales deal before a pricing or concession conversation - Respond to a customer discount request without immediately caving on price - Counter a price reduction demand by broadening the negotiation beyond price - Structure your concession sequence so you trade low-value items first and protect margin - Avoid proactive discounting, escalating concession patterns, or ultimatum traps - Apply the DuPont four-step negotiation framework (Acknowledge & Defer → Deepen & Broaden → Explore & Compare → Concede According to Plan) - Use the Situational Sales Negotiation (SSN) pre-call planning template to score concessions before the call - Build scripted deferral language to buy time without threatening the deal - Prepare for a challenger negotiation with constructive tension - Draft a pre-call negotiation work