How to Successfully Navigate High-Stakes Sales Conversations

Winning a sale means shaping the customer’s point of view. Preconceived notions have deep roots, and the sales professional must dig deep to find them. This high-risk, high-reward pursuit is necessary in an economy in which more sellers are attempting to engage fewer customers.

There are skills sales professionals must master to effectively engage their customers in high-stakes sales conversations: asserting a point of view, building alignment among stakeholders, and accessing senior-level decision-makers.

Asserting a Point of View

Sales professionals have the challenge of navigating and, ultimately, reshaping their buyer’s thinking. They must widen the customer’s purview, revealing the full scope of risks and opportunities. There are four key ways to do this:

  • Articulate meaningful observations in concise, everyday language that is free of jargon.
  • Normalize discussions of risk. Rather than attempt to defray all risk, cite the balance between risk and reward.
  • Balance discussions of risk with expected benefits. Doing so moves the customer through the decision process.
  • Check that the solution value resonates with customers by using reflection questions. Listening and responding to their answers helps shape their points of view.

Building Alignment

Purchasing decisions today occur across many stakeholders. Creating alignment among these groups is difficult because differing emotions are in flux.

Fears of moving forward are often rooted in the components of self-determination theory. This theory asserts that humans have an inherent psychological need for autonomy, competence, and relatedness. Fear of losing control threatens our need for autonomy. Fear of making the wrong decision threatens our need for competency. Finally, our need to connect with others — that is, relatedness — is threatened by fears of diminished reputation.

To build alignment, sales professionals need strategies to address these concerns. You can do this by:

  • Understanding the source of misalignment, which often stems from fear or miscommunication.
  • Coalescing the needs and concerns of various stakeholders into one coherent case for change. Each stakeholder needs to know that they have been heard.
  • Advancing the sale by managing risk. Starting with the decision maker who feels most threatened by the prospect of change.
  • Understanding that stakeholder alignment is a dynamic process because the buyer’s journey is a dynamic process.

Accessing Senior Decision-Makers

A complex, high-stakes sale will almost always involve numerous stakeholders. Unfortunately, it will also involve challenges in reaching those stakeholders. Sales professionals often find themselves engaging procurement professionals before having a chance to speak with senior level decision makers.

Frequently, the initial contact is not the person who will make the final determination. Once the sales professional gains access, they need to understand the decision makers’ needs, overcome their objections, and build trust. Some ways sales professionals can get in front of senior decision-makers include:

  • Building a foundation for the request to meet with senior level decision makers with a value statement built around the issue, action, and value.
  • Developing resonant messaging by performing prework that yields insights that are salient to the customer. Contextualize insights around the customer’s challenges by using the framing effect.
  • Fostering trust through transparency. The act of sharing information is just as important as the content of the information.

Building the skills that empower your sales professionals to confidently engage their customers in high-stakes sales conversations serves to increase win rates and deal size, while reducing cycle time and improving resource utilization.


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