Why Context & Situational Understanding Should Guide Your Go-To-Market Strategy

  • Written by Alice Walmesley & Tom Cosgrove, Gartner
  • Published in Demanding Views

Never has it been clearer that the B2B sales playbook that got us here will not get us where we need to be. The traditional sales model driven by seller interaction is increasingly out of sync with B2B buyers’ preferences for rep-free purchases. While reps play a critical role in engaging customers and closing deals, their perceived inability to align with stakeholder and buying group issues and the emotional tone of a purchase means that customers deliberately avoid them. In fact, Gartner research shows that more than 43% of B2B customers prefer to not interact with a sales rep at all.

Meanwhile, despite customers’ growing preference to avoid direct seller engagement, those that do so display higher levels of purchase regret. The very behavior B2B buyers are seeking is damaging their own chances of a good purchase outcome! Reps have the potential to deliver significant value to customers, but their ability to do so will rely on a different approach to what was valuable to customers previously.

Help Them Make Sense Of All The Information

Sales organizations have responded to customers’ reluctance to engage with sellers by doubling down on improving seller expertise and arming them with high-quality information to prove their worth. However, the amount of high-quality information available for customers to use when making a B2B buying decision has become overwhelming, leading to indecision and a sharply reduced likelihood of making a substantive purchase. Rather than adding to the noise, the best-sellers often help buyers simply make sense of the information they’ve already encountered. Gartner calls this approach “Sense-Making,” and is often distilled down to sellers’ abilities to harness and include customer context in their buyer engagement strategies.

While sense-making is an approach taken by the most successful sellers, it is not solely a seller competency. Nor should sense-making be seen as one-size-fits-all when layered into a commercial interaction. Attempts to connect, clarify and collaborate around buyers’ needs fall short when they are employed ignorant of customer context. As all customers' buying situations are unique, it is increasingly important to deploy bespoke approaches that leverage situational differences to provide empathetic and focused support.

Tailor With Situational Awareness

The clearest path to selling success lies at the intersection of sense-making tactics and what we call “situational awareness.” Situational awareness is built upon the premise that every buying situation is unique, but with patterns that repeat across organizations. Organizations that enhance sense-making (or any other standardized methodology for that matter) with awareness of buyers’ unique “situations” and actions to accommodate for those differences can strengthen confidence with customers, partners and prospects across various purchase types, geographies, industries or whatever differentiates a particular buyer’s circumstances. As each buyer’s journey has become increasingly unique, we need to meet customers where, when and how they want to be engaged with guidance that is directly relevant to their current situation.

To allow sellers to successfully exercise agility, chief sales officers (CSOs) and other sales leaders should invest in enablement to build a scalable understanding of buyer context and using the right content to support buyers in moving toward the next job or task of their process. Therefore, rather than deploying a single, linear playbook for sellers to follow, sales organizations should seek to build sellers’ situational awareness competencies and provide tools that ease the context gathering burden with three primary inputs in mind:

  • Customer buying job(s): Analytics that track customers’ digital behavior and information gathered during sales meetings can indicate the buying task(s) a customer is working on. CSOs and their support teams should map the common customer buying tasks and identify common challenges, including information-related challenges that customers face when making a purchase.
  • Customer context for the purchase: CSOs should identify the common situations, varied stakeholder involvement and broader customer organizational reasons for purchases.
  • Customer purchase type: Customers behave differently depending on how new or disruptive a purchase is, and therefore CSOs should create different scenario plans according to whether the purchase type is cross-sell, upsell, renewal or expansion.

Situations can be extremely varied but often come down to common patterns, purchase types and distinct needs that arise. Using situational awareness and empathy to deliver the type of purchase experience that customers value requires:

  • Analysis of first- and third-party data to diagnose and act upon any differences in selling approaches required by purchase type and specific context. This can be achieved through the employment of Revenue Data Solutions.
  • A will to deviate from complete standardization to a more personalized approach guided by a flexible governance framework.
  • Regular sensing of customer purchase challenges beyond the typical one-and-done buying journey mapping exercise at an “average” buying group versus individual stakeholder level.
  • Linking common customer buying and information-related challenges to tactical buyer support, segmented with situational tuning.

There is a huge opportunity for sales leaders to build an environment where situational understanding and more empathetic behaviors are focal points for optimizing commercial efforts. Commercial teams that work to understand the customer’s perspective and tune their approach based upon those nuances will outperform competitors by successfully boosting customer decision confidence and making the purchase easier.


Alice Walmesley is a director, advisory, at Gartner and Tom Cosgrove is a senior director, analyst, at Gartner.