Challenger sales methodology: 5 steps for success in 2026

Sales teams often know their product inside and out. Every feature, benefit, and competitive advantage has been memorized. Yet deals still stall in the final stages, and prospects still choose competitors despite a superior solution. The issue isn’t product knowledge, but approach.

The Challenger sales methodology flips traditional relationship-building on its head. Instead of responding to customer needs, Challenger sellers teach prospects about problems they didn’t know they had. They bring cross-industry insights that reframe how buyers think about their business. They take control of conversations with data and perspectives that competitors can’t match. Research from Gartner (formerly CEB) shows Challenger sellers win 40% more deals than their peers because they align with how B2B buyers actually make decisions.

This guide walks through the complete Challenger sales methodology, from understanding the core framework to implementing it across revenue teams.

Key takeaways

• Master the Three T’s to win 40% more deals: teach customers new perspectives with commercial insights, tailor messages to each stakeholder’s priorities, and take control of conversations with data-driven confidence.
• Focus on commercial insights, not product features: bring surprising, relevant information that challenges customer assumptions and connects directly to their business challenges; this differentiates you when products become commoditized.
• Map and engage every decision-maker systematically: B2B purchases involve six to ten stakeholders with different priorities, so identify all players early and adapt your core message to resonate with each person’s specific role and concerns.
• Track Challenger behaviors with real-time CRM analytics: platforms like monday CRM enable revenue teams to monitor insight delivery frequency, stakeholder engagement rates, and conversation control metrics that predict deal success and identify coaching opportunities.
• Implement systematically across your entire team: assess current capabilities, develop commercial teaching strategies, build stakeholder-specific messaging, and coach with data-driven insights to see measurable improvements in six to twelve months.

What is the Challenger sales methodology?

The Challenger sales methodology is a research-backed approach where sales reps teach customers new perspectives about their business, tailor insights to specific stakeholders, and take control of sales conversations. Rather than just building relationships or responding to stated needs, Challenger sellers bring unique insights that reframe how customers think about their problems through a distinct sales strategy.

This methodology came from CEB’s (now Gartner) research on over 6,000 sales reps. They discovered something surprising: top performers don’t just build relationships. They win by bringing cross-industry perspectives and data that shift how customers see their own business.

A Challenger seller might reveal hidden costs in a prospect’s current approach that outweigh perceived switching costs, or introduce competitive threats the customer hasn’t considered. The approach works particularly well in complex B2B sales environments where buyers have extensive information but lack the broader perspective that experienced salespeople bring.

The 5 seller profiles every sales leader should know

The original research identified five distinct seller profiles based on behavioral patterns and performance outcomes. Understanding these profiles helps sales leaders identify which reps have natural Challenger traits and which need development.

The original research identified five distinct seller profiles based on behavioral patterns and performance outcomes. Understanding these profiles helps sales leaders identify which reps have natural Challenger traits and which need development, as each brings different strengths to the sales process.

• Hard Worker: shows exceptional work ethic, arrives early, stays late, follows up consistently with prospects, never gives up on opportunities.
• Relationship Builder: prioritizes strong personal connections with clients, focuses on customer service and responsiveness, maintains long-term relationships after deals close.
• Lone Wolf: operates independently with minimal oversight, follows personal instincts rather than prescribed processes, and achieves results through unconventional methods.
• Reactive Problem Solver: responds quickly to customer issues, excels at addressing technical questions, provides detailed product knowledge and reliable service.
• Challenger: teaches customers new perspectives about their business, tailors messages to different stakeholder priorities, takes control of sales conversations with data and insights.

While all profiles can achieve sales success, Challengers consistently outperform others in complex B2B sales environments when supported by a well-defined sales process. They excel particularly when deals involve multiple stakeholders and extended sales cycles.

Why do Challengers win 40% more deals?

Challengers outperform other seller profiles because they align with how B2B buyers make decisions. B2B buyers complete extensive research before engaging sales teams, using an average of 10 channels across the purchasing cycle and arriving with predetermined requirements and vendor shortlists.

B2B buyers expect insights they can’t find on their own. Sure, they’ve got product specs, reviews, and competitor comparisons at their fingertips. But what they’re really looking for? Cross-industry trends, competitive intelligence, and data that speaks directly to their specific challenges.

Complex B2B purchases typically involve six to ten decision-makers with different priorities, and eight in ten B2B decision-makers will actively look for a new vendor if performance guarantees aren’t offered. Challengers excel at identifying all stakeholders, understanding their unique perspectives, and tailoring insights to address each person’s specific concerns. This comprehensive stakeholder engagement accelerates decision-making and reduces the risk of late-stage objections.

When products and services become commoditized, the insights salespeople bring become the primary differentiator. Challengers prevent stalled deals by proactively addressing obstacles, challenging status quo bias, quantifying the cost of inaction, and providing stakeholders with the business case they need to move forward.

Master the 3 T's of Challenger selling

The three T’s form the core framework that defines Challenger methodology. These aren’t sequential steps but interconnected capabilities that work together throughout every customer interaction. Mastering each component enables sales teams to differentiate through insights rather than features.

1. Teach with commercial insight

Commercial insight isn’t just information; it’s perspective that reshapes how prospects think about their business. Unlike basic product knowledge or industry trends, real commercial insights surprise prospects, connect directly to their situation, and point toward action, all while subtly leading to your solution without feeling like a pitch.

Effective commercial insights must meet specific criteria:

• Challenge assumptions: present information the prospect hasn’t considered, revealing blind spots in their strategy.
• Connect directly: link to the prospect’s business model, competitive position, or operational challenges.
• Drive action: lead to specific steps the prospect can take, whether investigating hidden costs or exploring new strategies.
• Provide evidence: support claims with data, patterns, or cross-client examples.

Commercial insights emerge from industry research, customer data analysis, and cross-client pattern recognition. When a salesperson notices that companies implementing specific operational changes achieve 30% faster time-to-market across multiple clients, this pattern becomes a commercial insight for prospects who haven’t made those changes.

2. Tailor your message to each stakeholder

B2B purchases involve multiple stakeholders with fundamentally different priorities and decision-making criteria. Tailoring means adapting your core commercial insight to resonate with each stakeholder’s specific role and interests.

Different stakeholders require different messaging approaches:

• Economic buyer: focuses on ROI, budget impact, and strategic alignment — emphasizes financial implications like revenue at risk from competitive threats.
• Technical buyer: concerned with implementation complexity and system integration — addresses technical feasibility and required resources.
• User buyer: interested in day-to-day usability and workflow impact — shows how solutions improve their specific processes.
• Coach/Champion: your internal advocate who helps navigate the organization — provides stakeholder-specific talking points they can use.

Stakeholder mapping is essential for effective tailoring. During discovery, identify all potential stakeholders, understand their roles and priorities, and track their communication preferences. Revenue teams find success using a centralized CRM to maintain detailed stakeholder profiles throughout long sales cycles, tracking each person’s concerns, preferred communication channels, and engagement patterns.

3. Take control of the sales process

Taking control means proactively guiding the conversation and sales process rather than reactively responding to customer requests. This demonstrates confidence and helps prospects navigate complex buying decisions more effectively.

Control manifests in several key ways:

• Structure meetings: lead with agendas that advance the sale rather than letting customers dictate conversation flow.
• Ask tough questions: probe into areas customers might prefer to avoid, such as budget constraints or competing priorities.
• Challenge assumptions: respectfully question beliefs when data suggests alternatives exist.
• Drive next steps: propose specific actions and timelines rather than waiting for customer direction.
• Guide evaluation: suggest criteria based on what actually predicts success and help prospects avoid common mistakes.

Questions like “What happens if you don’t solve this problem in the next six months?” force prospects to confront the cost of inaction and create urgency around decision-making.

5 steps to implement the Challenger sales method

Understanding Challenger methodology differs fundamentally from successfully implementing it across a sales team. Each organization must adapt the approach to their specific context, sales cycle, and market dynamics. These five steps provide a systematic framework for rolling out Challenger methodology effectively.

Step 1: identify and develop Challenger behaviors

Assess current team capabilities to identify who demonstrates natural Challenger tendencies versus who needs significant development. This assessment should evaluate multiple dimensions of Challenger behavior rather than relying on subjective manager opinions.

Key assessment criteria for identifying Challenger potential:

• Comfort with challenging assumptions: does the rep respectfully push back on questionable statements or simply agree to maintain rapport?
• Teaching ability: does the rep bring new perspectives to customer conversations or primarily present product features?
• Message tailoring skills: does the rep adapt their approach for different stakeholder types or deliver the same pitch regardless?
• Conversation control: does the rep guide the sales process proactively or let customers dictate pace and direction?
• Track record of insights: do customers reference learning something new from this rep or view them primarily as a product expert?

Create an evaluation rubric scoring each rep on these criteria using a onetofive scale. Reps scoring four to five across most criteria are natural Challengers who need refinement. Those scoring two to three can develop Challenger skills through focused training.

Step 2: create your commercial teaching strategy

Develop a systematic approach to creating commercial insights that sales teams can use consistently. This centralized approach ensures quality control while reducing the burden on individual salespeople to become industry experts overnight.

Build your insight development process around key research areas:

• Industry trend analysis: monitor trade publications and analyst reports to identify emerging trends affecting target customers.
• Customer data mining: analyze patterns across your customer base to identify what separates high performers from struggling ones.
• Cross-client learning: document lessons from customer implementations to develop insights about what works in specific situations.
• Competitive intelligence: track competitor moves and market positioning to understand how your customers’ competitive environment evolves.

Transform raw data into compelling stories that resonate emotionally while remaining factually grounded. An insight about supply chain risk becomes more powerful when illustrated with a specific example of a company that suffered unexpected disruptions.

Step 3: build stakeholder-specific messaging

Systematically adapt core insights for different stakeholder types using a repeatable framework. This structured approach ensures consistent quality while making it easier for reps to execute Challenger methodology effectively.

Map the complete buying committee early in the sales process, including people who might not attend meetings but influence decisions behind the scenes. Research each stakeholder’s position, responsibilities, and likely concerns based on their role.

Consider how a commercial insight about digital transformation in manufacturing would be tailored:

• For the CFO: emphasize that companies delaying digital transformation face 25% higher operating costs within three years.
• For the IT director: focus on how legacy systems create integration challenges that compound over time.
• For the operations manager: highlight how manual processes slow response times to customer requests.

Organizations achieve results when they leverage modern platforms like monday CRM for systematic stakeholder tracking, recording each decision-maker’s concerns, questions, and engagement patterns throughout long sales cycles.

Step 4: coach your team with data-driven insights

Challenger coaching requires different approaches than traditional sales coaching. The behaviors being developed are more nuanced than simple activity metrics like calls made or meetings scheduled, so coaching must focus on skill development rather than just output.

Focus coaching on specific skill development areas:

• Insight development and delivery: Help reps identify patterns in customer data and practice delivering insights in compelling ways.
• Stakeholder identification: train reps to systematically identify all stakeholders early and develop engagement strategies for each
• Conversation control techniques: practice guiding customer conversations toward productive outcomes while remaining collaborative.
• Objection handling: develop the ability to respectfully push back on customer assumptions with data and insights.
• Discovery questions: master asking questions that uncover stakeholder priorities and validate commercial insights.

Implement varied coaching methods including role-playing challenging conversations, insight development workshops where teams analyze customer data collaboratively, and peer learning sessions where top performers share their approaches. Teams discover that advanced solutions like monday CRM enable them to track behavioral patterns and performance metrics that inform coaching priorities.

Step 5: measure success with CRM analytics

To understand whether Challenger implementation is progressing effectively, you must track both leading indicators (behaviors) and lagging indicators (results). This dual focus provides a complete picture, connecting the team’s daily actions to high-level business outcomes.

Leading indicators to monitor:

• Discovery call duration: Challenger conversations typically run longer because teaching and challenging takes more time than presenting features.
• Stakeholder engagement rates: number of unique stakeholders contacted per opportunity and frequency of interactions.
• Insight delivery frequency: how often reps reference commercial insights in customer communications.
• Educational content usage: frequency of sharing insight-based content versus product-focused materials.

Lagging indicators to track:

• Win rates: overall close rates and segmentation by deal size and complexity.
• Deal velocity: average sales cycle length from initial contact to close.
• Average deal size: whether Challenger selling leads to larger deals as teaching uncovers broader needs.
• Pipeline progression rates: how quickly opportunities move from stage to stage.

Build dashboards that track these metrics over time. Establish clear baselines before rolling out Challenger methodology, then set targets aligned with your industry benchmarks. Measure performance consistently and compare results against established standards to assess progress.

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Compare Challenger to other sales methodologies

Understanding when and why to choose Challenger over other methodologies helps sales leaders make informed decisions about which approach fits their specific sales environment. Each methodology serves different buyer types and sales complexity levels.

Challenger vs. solution selling

Solution Selling has been a go-to methodology for decades, but how does it stack up against Challenger? The key difference lies in who drives the conversation and when value gets introduced.

Solution Selling works well when customers have defined problems and actively seek solutions. Challenger becomes more effective when customers may not fully understand their challenges or when differentiation comes through insights rather than product features.

Challenger vs. SPIN selling

SPIN Selling revolutionized sales questioning techniques, but Challenger takes a fundamentally different approach to information exchange. While SPIN extracts information from customers, Challenger delivers insights to them.

SPIN Selling excels at uncovering customer needs through systematic questioning. Challenger focuses on teaching customers about needs they didn’t know they had by presenting external insights and data.

Challenger vs. MEDDIC

MEDDIC and Challenger serve different purposes in the sales process, which is why many high-performing teams use them together. MEDDIC tells you what to qualify, while Challenger tells you how to sell.

MEDDIC helps ensure proper qualification and process management. Challenger provides the approach for customer interactions within those qualified opportunities. Many organizations successfully combine both methodologies.

Accelerate Challenger adoption with AI and automation

AI and automation solve specific Challenger implementation challenges around insight development, stakeholder tracking, and coaching at scale that previously required extensive manual effort. These technologies make Challenger methodology accessible to teams without dedicated research resources.

Generate commercial insights at scale

AI helps sales teams develop and maintain commercial insights more efficiently than manual research alone. This capability is particularly valuable for mid-market teams lacking dedicated research resources.

AI systems monitor thousands of news sources, research reports, and market data feeds to identify emerging trends. Automated tracking of competitor announcements and customer reviews provides real-time competitive insights. Natural language processing extracts key findings from lengthy research reports, summarizing insights relevant to specific industries.

AI analyzes patterns across customer implementations to identify what separates high-performing customers from struggling ones. For example, AI might identify that companies completing specific onboarding steps within 30 days achieve ROI 40% faster. This pattern becomes a commercial insight for prospects about the importance of early implementation investment.

Revenue teams gain value when they use CRM platforms with AI capabilities that extract information from customer interactions, summarize communication patterns, and suggest relevant insights based on similar customer profiles.

Automate stakeholder tracking

Automation solves one of Challenger’s biggest implementation challenges: managing complex stakeholder relationships across multiple deals without losing track of individual preferences and concerns.

AI-powered automation transforms stakeholder management in several key ways:

• Automatic stakeholder identification: AI identifies stakeholders mentioned in emails, meeting notes, and CRM records, building organizational charts that show reporting relationships and influence patterns.
• Communication pattern analysis: machine learning analyzes response patterns to determine each stakeholder’s preferred communication channels, optimal contact times, and content format preferences.
• Engagement tracking and alerts: automation monitors stakeholder behavior like email opens and content engagement, triggering alerts when engagement patterns change or opportunities arise.

For example, automation might track that a CFO stakeholder consistently opens emails containing ROI data but rarely engages with technical content, responds most frequently to Tuesday morning messages, and has become less responsive recently. This triggers alerts for the sales rep to reach out with financially-focused insights at the optimal time.

Enable real-time sales coaching

AI and automation scale Challenger coaching beyond what sales managers can accomplish through manual call reviews and periodic one-on-ones.

Natural language processing analyzes recorded sales calls to identify Challenger behaviors and flag missed opportunities for coaching discussions. AI provides in-call suggestions for insights to deliver, questions to ask, or objections to address based on conversation context. Machine learning identifies patterns across successful and unsuccessful deals, suggesting coaching priorities based on which behaviors correlate most strongly with wins.

AI might analyze a sales call and identify that the rep delivered a strong commercial insight but failed to challenge the prospect’s assumption about internal resources handling implementation. The system flags this as a coaching opportunity and suggests specific language the rep could have used.

Transform your revenue team with monday CRM

Organizations achieve measurable improvements in Challenger methodology adoption when they leverage comprehensive CRM platforms that specifically support teaching, tailoring, and taking control at scale. The right technology foundation accelerates skill development and ensures consistent execution across the entire sales team.

Track Challenger behaviors in real time

Real-time visibility into Challenger implementation helps sales managers identify coaching opportunities and recognize successful execution as it happens. Modern platforms like monday CRM provide this immediate feedback loop that accelerates skill development and ensures consistent methodology adoption.

Monitor key Challenger behaviors with real-time tracking capabilities:

• Conversation quality metrics: track call duration, participant engagement, and conversation topics to identify whether reps are conducting substantive Challenger conversations that teach and challenge rather than just present features.
• Stakeholder engagement patterns: automated tracking of email opens, content downloads, and meeting attendance across all decision-makers shows which reps effectively engage the full buying committee with tailored insights.
• Deal velocity indicators: real-time measurement of how Challenger behaviors impact deal progression identifies which activities actually move opportunities forward and which need refinement.
• Coaching alerts: when stakeholder engagement numbers drop or deal velocity slows, automated alerts trigger coaching conversations focused on specific Challenger behaviors that need improvement.

Scale commercial teaching with AI

AI capabilities specifically support the “Teach” component of Challenger methodology by helping sales teams develop insights faster and personalize them more effectively. monday CRM democratizes commercial teaching, making it accessible to teams without dedicated research resources.

Extract patterns from customer interactions, implementation data, and success metrics to identify what separates high-performing customers from struggling ones. Monitor market data, competitive intelligence, and industry research to identify emerging trends affecting target customers.

Analyze which insights drive the most stakeholder engagement and pipeline progression, continuously refining the insight library based on what actually works. Automatically adapt core insights for different industries, company sizes, and stakeholder types, creating tailored versions without requiring sales reps to manually customize every presentation.

Unite sales, marketing, and customer success

Organizational alignment across the revenue team ensures Challenger methodology extends beyond initial sales into the entire customer lifecycle. Consistent experiences for customers get created while the value of commercial insights across all touchpoints gets maximized with monday CRM.

Marketing and sales collaborate to develop commercial insights, with marketing providing research and thought leadership while sales contributes frontline customer intelligence. A centralized repository of Challenger content accessible across teams ensures everyone uses current, approved insights.

Customer success insights about implementation challenges and expansion opportunities inform new commercial teaching points that sales uses with prospects. Complete visibility into the stakeholder journey from marketing engagement through sales conversations to customer success interactions prevents disconnected experiences.

“There’s probably about a 70% increase in efficiency in regards to the admin tasks that were removed and automated, which is a huge win for us.“

Kyle Dorman | Department Manager - Operations, Ray White

"monday CRM helps us make sure the right people have immediate visibility into the information they need so we're not wasting time."

Luca Pope | Global Client Solutions Manager at Black Mountain

“In a couple of weeks, all of the team members were using monday CRM fully. The automations and the many integrations, make monday CRM the best CRM in the market right now.”

Nuno Godinho | CIO at Velv

Build your Challenger sales advantage

Challenger methodology transforms how sales teams engage with informed B2B buyers by leading with insights rather than features. The approach requires systematic implementation across insight development, stakeholder engagement, and conversation control. Organizations that commit to the process see measurable improvements in win rates and deal velocity.

Success depends on matching the right methodology to your sales environment. Challenger works best in complex B2B sales with multiple stakeholders and extended decision cycles. Teams selling to well-informed buyers who’ve already completed extensive research benefit most from the teaching and challenging approach.

The combination of a proven methodology with a comprehensive CRM platform accelerates adoption and scales impact across entire revenue teams. Organizations that leverage platforms like monday CRM to track Challenger behaviors, automate stakeholder management, and enable real-time coaching see faster skill development and more consistent execution, with companies achieving best-in-class value-realization practices seeing about 7 percentage points higher net revenue retention than peers.

The content in this article is provided for informational purposes only and, to the best of monday.com’s knowledge, the information provided in this article is accurate and up-to-date at the time of publication. That said, monday.com encourages readers to verify all information directly.