Effective sales professionals are recognizing that the skills they need to compete today look different from conventional selling capabilities. This change is a result of business needs and solutions’ becoming more complex than ever before.

Today’s buyers need solutions that go beyond the product or service being sold – they need partners who add value and help them meet strategic goals. Meeting these needs means that sales professionals need to build the confidence and skills required to engage their buyers in high-stakes dialogues.

A high-stakes dialogue is a conversation that is high-risk and high-reward for the sales professional. It’s high-risk because the conversation has the potential to make the customer feel pressured, bring to light a perspective that the customer does not want to hear, make the sales professional come across as pushy or self-serving, or create conflict. High-stakes conversations are high-reward because executing them properly delivers opportunities to help the customer clarify his or her thinking, build trust, and accelerate the decision-making process.

Effectively executing high-stakes sales conversations requires sales professionals to learn three critical skills: asserting a point of view to shape customer thinking, building alignment among stakeholders and “uptiering” to gain access to key decision-makers.

Here, we explore these skills in greater detail.

Asserting a Point of View

Sales professionals who have the ability to assert a perspective that guides or reframes their customer’s thinking can add significant value to the sales dialogue. However, asserting a strong point of view can be risky, because an unskilled sales professional can alienate customers by coming on too strong.

To effectively add value to the sales conversation by asserting a point of view, sales professionals should:

  • Make it clear that their interests are aligned to the customer’s (This preliminary step creates an environment that is more conducive to asserting a point of view.)
  • Use concise, compelling language to deliver the message
  • Ask for the customer’s response (To advance the dialogue, sales professionals need to know if the solution capabilities resonate with the customer’s needs.)

Building Alignment

Purchasing decisions today occur across many stakeholders. In fact, according to an article published by CEB (now Gartner) leaders in the Harvard Business Review, the average number of people involved in the B2B decision-making process is 6.8. Adding to this complexity is that fact that these stakeholders come from “a lengthening roster of roles, functions, and geographies.” Ensuring that this complex web of decision-makers is all on the same page requires skill.

Here are some effective techniques for aligning a diverse audience of stakeholders:

  • Identifying the source of misalignment. In most selling scenarios, the source is fear or communication breakdown.
  • Weave differing customer perspectives into one case for change.
  • Address concerns surrounding risk.


In order to advance a sale, professionals need to understand and gain access to senior decision-makers. Gaining access is one challenge; effectively positioning value and understanding the decision makers’ needs, overcoming their objections and building trust is another challenge.

Gaining access and properly positioning solutions for senior-level decisions-makers requires sales professionals to:

  • Build a foundation for the request by illustrating a compelling case for meeting with the senior team
  • Develop resonant messaging through research and conversations about the information senior-level decision makers need with current account contacts
  • Contextualize insights around the customer’s challenges
  • Foster trust through transparency (The act of sharing information is just as important as the content of the information.)

Sales professionals who build the skills they need to effectively engage their buyers in high-stakes dialogues will experience the benefits of increasing win rates and deal size, reducing sales cycle duration, and improving resource use.