Why Delivering a Tailored Insight is Essential to Sales Success

The 2011 research that inspired “The Challenger Sale” revealed a surprising foundational fact: the sales experience is the single biggest driver of customer loyalty. Yet the gap between what buyers want and what sellers deliver is wider than ever. More than a decade of research shows us that sellers aren’t doing enough to engender that loyalty. What gives?

When we retested buyers’ opinions in 2020, they rated seller capability as down 40% from the previous year. The most critical skill to buyers, demonstrating unique insight, was down 52%.

This erosion of trust might be one reason that as recently as 2022, 75% of B2B buyers told Gartner they preferred a completely seller-free buying experience. Or why most sellers (89%) in our 2020 survey reported identifying their business problems themselves—without the input of sellers.

In an era of cringy AI-fueled outreach and “personalization at scale,” who can blame those buyers? To break through the garbage, sellers must deliver a story that deconstructs a buyer’s thinking, leads toward a new solution, and dismantles their underlying beliefs and assumptions. Challengers call it a Commercial Insight.

What is a Commercial Insight?

Challengers know to avoid the stale “What keeps you up at night?” question. Instead, they aim to tell customers what should be keeping them up. The Challenger Sales Methodology teaches sellers to execute this new approach through a six-step choreography that forms a Commercial Insight.

But what’s to be done in a new era of selling where buyers believe they already know what they need? Buyers move through nearly 90% of the sales process alone, and when they do finally reach out to sellers, these buyers arrive with solid perceptions. Sellers hoping to close in this environment must ask: “Is that perception reality? Do they truly understand their needs? And are they building consensus around something that exists in the marketplace?”
The second step in the choreography, known as the Reframe, gives sellers this opportunity. As they build their Reframe, they can directly address even the most entrenched beliefs of these highly-researched customers. Ideally, the right Reframe:

• Makes the customer think differently
• Drives toward action
• Leads to your solution
• And will reveal
  • An unrecognized problem
  • An underappreciated problem
  • A misunderstood cause of the problem

As sellers build their Reframes, our Principal Executive Advisor and Global Head of Insights and Messaging Michael Schaumberger recommends addressing three problems. Learn more in this short clip from our recent on-demand webinar.

How do you ensure your Reframe compels your prospects to act?

The Importance of Tailoring

Tailoring – one of the four foundational Challenger skills – happens when sellers use their understanding of what’s driving the customer to customize their message for resonance. Challengers know how to deliver the right message to the right person at the right time.

Many programs, approaches, and tools offer alternatives to Tailoring that promise significant results with minimal effort. However, Tailoring for resonance involves going far beyond knowing details about a person’s professional or personal experiences. It sometimes means delivering a different message to each stakeholder, understanding pain points throughout an organizational chart, and even changing your message in the middle of a call based on answers to your pointed questions.
It isn’t easy – and it’s often executed incorrectly.

Ineffective Tailoring looks like:

• Delivering the same message to everyone
• Tailoring to only one level
• Offering the wrong message to the right stakeholder (i.e., don’t give Procurement a demo)

Effective Tailoring looks like:

• Aligning messaging to industry and company
• Customizing to the role and personality of the individual stakeholder
• Drawing additional insights as new stakeholders enter the conversation and bring them up to speed

Tailoring helps sellers earn the right to deliver Commercial Insight. When executed correctly, the Challenger Choreography helps establish sellers as trusted advisors—a role that few can claim, according to our research on buyer perception. This is only possible with a level of understanding, perspective, and thoughtfulness achieved through intense planning and earned experience. While that may be daunting, one essential skill most sellers are already practicing that immediately helps them improve their Tailoring is listening.

While most successful sellers already practice “active listening” (if they didn’t, they likely wouldn’t be successful), few are skilled enough to listen in a way that allows them to synthesize and build a Reframe on the fly. In this short clip from our on-demand webinar, Challenger Account Executive Charryse Bigger explains why developing this muscle can aid your Tailoring efforts.

A Tailored Insight Earns Buyer Trust

Buyers are smart, savvy, and sick of generic sales pitches—but they’re also still looking for a guide. Challengers succeed by reframing their customers’ thinking and pointing directly to a solution only they can provide. No matter how far along buyers may think they are in a purchase process and how rep-free they may think they want their experience to be, a successfully Tailored Reframe can change their thinking and give sellers an opportunity to earn their place as trusted advisors.

For more on building a successful Reframe, including a tear-down of two real-life examples, watch our on-demand Winning The Challenger Sale Webinar, How to Build a Successful Reframe.