Mastering Situational Fluency & Flexibility in Sales Teams | Adapt to Buyer Expectations

Building Situational Fluency and Flexibility in Sales Teams

Effective sales leaders know their teams must be adaptable and prepared to meet buyers' ever-changing needs. Situational fluency—the ability of salespeople to adapt their messaging and approach to align with each buyer's specific challenges and objectives—is among the many skills needed to achieve this.

Situational fluency is especially critical in a world where rapid product innovation, new market development, and shorter product life cycles have become the norm. Salespeople must stay agile, ready to engage buyers with relevant and insightful conversations that demonstrate a clear understanding of the buyer’s context.

However, recent research from Forrester and HubSpot highlights an existing gap in sales performance:

• 77% of buyers say salespeople don’t understand their issues or how to help.
• 70% claim salespeople are unprepared for the questions they ask.
• 78% of executive buyers report that salespeople fail to provide relevant examples or case studies.

These findings suggest that even with significant investment in product and skills training, many sales teams struggle to fully embrace a consultative selling approach. The challenge lies in translating product knowledge into the ability to offer strategic, value-driven conversations that resonate with buyers’ specific needs.

Situational Fluency in the Modern Sales Landscape

In the book The Collaborative Sale, Keith Eades and Tim Sullivan explore how the concept of situational fluency has evolved to meet the demands of today’s buyers. Salespeople who possess situational fluency demonstrate the knowledge, skills, and attitude that modern buyers expect in their interactions with sales professionals.

Buyers have more access to information than ever before. As a result, they are more empowered in their purchasing decisions and evaluations. They now prefer to interact only with sellers who understand their business, their situations, their challenges, and their opportunities. Generalist sellers are no longer welcome in the sales process; buyers want to work with expert specialists who can bring new insights and add value, helping them solve problems and create new opportunities.

In fact, the buyer journey has fundamentally changed. According to research conducted by McKinsey, emotional bonds and loyalty with solution providers come only after the buyer recognizes the value. “Likability” alone is no longer a guarantee of sales success, as today’s buyers demand more than just rapport—they want value, insight, and expertise.

5 Key Components of Sales Situational Fluency

Eades and Sullivan describe five key components of situational fluency that salespeople must master to align with today’s buyer preferences:

• Situational Knowledge – the awareness of a buyer’s circumstances, as well as the understanding of the implications of that situation based on the seller’s experience or learning. A thorough knowledge and understanding of the buyer’s industry, trends, key players, problems, challenges, opportunities, and desired results is a requirement for sellers today.
• Capability Knowledge – the understanding of a solution provider’s products or services, and how those capabilities can be converted into desired results. Sellers need to know what their capabilities do for customers, and not just what the capabilities are.
• People Skills – people buy from people, and they are much more likely to buy from people whom they like. Therefore, sellers must possess good interpersonal skills, so that they can appeal to buyers’ emotions, as well as their intellect.
• Selling Skills – the ability to execute essential selling functions, such as stimulating buyer interest, qualifying opportunities, identifying buyer needs, diagnosing problems, presenting solutions, conveying value, negotiating, and closing.
• Collaborative Attitude – the ability to work with buyers to create or enhance solutions in a spirit of openness and transparency, and to demonstrate that they are acting with the buyer’s interests in mind first.

Practicing Situational Fluency in the Field

While these components represent the necessary competencies for today’s salespeople, they must be expressed in a way that aligns with how modern buyers want to engage. Unfortunately, even well-trained sellers may struggle to implement situational fluency effectively, especially if they fall back on outdated sales techniques.

For instance, one of Richardson’s clients had previously invested in training from another provider that focused on industry and product training, coaching, and improved content resources—but they were not seeing the expected results. After investigating how these sellers were engaging with customers, it became clear why some were still struggling.

Some sellers were still using "old school" sales methods: starting with pitching product capabilities to find a potential fit and then pushing to close a sale. This approach didn’t resonate with the buyers, who demanded to see value and insight before committing to a relationship with a seller. This strategy overemphasized product knowledge while de-emphasizing the collaborative attitude and situational knowledge needed to truly connect.

In contrast, high-performing sellers demonstrated situational fluency differently. They began by studying each buyer’s situation in detail, hypothesizing what capabilities would provide the most value. Then, they presented these insights to the buyer, earning the right to collaborate further. Once the buyer recognized the value of the solution, they were more willing to build a relationship with the seller, who could then guide them toward a buying decision.

Achieving Situational Fluency and Flexibility in Your Sales Teams

To address these challenges, sales organizations need a structured approach that integrates messaging, training, and continuous feedback. Here are three practical ways to develop situational fluency and flexibility:

Solution Messaging Training
This is a learnable and repeatable process that helps marketing teams accurately identify key buyer personas, prioritize their critical business issues, and craft messaging that positions the value of a solution. By aligning messaging with buyer-specific needs, salespeople can engage in more meaningful conversations and establish themselves as trusted advisors.

Sales Tool Utilization
Sales teams can use tools that capture the key business challenges of each buyer role, the underlying causes, and the capabilities required to address them. These tools provide salespeople with a roadmap for understanding the customer’s business environment and how their products or services solve pressing issues. This structured approach enables more fluent and confident conversations.

Conversational Intelligence Practice
Conversational intelligence tools provide an innovative way for sales professionals to study specific business issues, their causes, and the capabilities needed to solve them. These tools help salespeople practice their conversational skills to ensure a consistent level of expertise across the team and enhance situational fluency. Richardson's Accelerate Sales Performance System helps salespeople practice their conversational intelligence skills using "pitch back" technology that allows them to record practice pitches and share them with their managers for feedback.

Driving Agility in Changing Markets

In today’s market, changes happen fast, and sales teams need to adapt quickly. This is especially challenging for distributed teams, where disseminating new messaging and ensuring its adoption can be difficult. Organizations need situational flexibility—the ability to react swiftly to market shifts and new buyer demands.

Here’s how to build and maintain this flexibility:

• Tailor Knowledge by Role: Understanding the specific competencies required for each role within the sales team allows you to deliver the most relevant training to the right people.
• Rapid Learning Sprints: Deliver short, focused training sessions that provide salespeople with the information they need immediately.
• Empower Sales Leaders: Ensure sales leaders are equipped with the tools and sales management training they need to coach their teams effectively. Leaders should be prepared to address not just the business side but also the personal impact of change on their teams.
• Use Video Coaching for Skill Development: Implement video-based coaching sessions where salespeople can practice, receive feedback, and continue practicing until they master the content. This method helps embed new knowledge and ensures salespeople are confident when interacting with buyers.
• Measure and Hold Accountable: Update goals regularly to ensure they are aligned with current market conditions, and measure the outcomes to assess the direct impact of new messaging and training on performance.

Building situational fluency and flexibility is essential for sales teams to succeed. By integrating solution-focused messaging with rapid, role-specific training, and reinforcing new skills through ongoing coaching, sales organizations can ensure their teams remain agile, knowledgeable, and prepared to meet buyer needs. This agility is not only critical in