Increasing Win Rates | Sales Development | Wilson Learning Worldwide

Successful Sales Skills for Increasing Win Rate and Profitability

An Evidence-Based Strategy

Successful Sales Skills for Increasing Win Rate and Profitability

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The old adage claims that “customers love to buy, but hate to be sold to.” Turn that around to the seller’s perspective and salespeople would say that they love to win—but hate to lose.

In the current environment, winning is becoming increasingly difficult. Research by CSO Insights and Aberdeen shows that just 47% of forecasted business closes. A full third of forecasted business is lost, and 21% of opportunities stall indefinitely.1

Salespeople’s drive to win is key to their success—but their drive combined with a challenging environment can cause them to pursue any deal at any cost, which means they invest time and resources on improbable and unprofitable deals.

Sales leaders want to help their salespeople win the right business, selling solutions that address customers’ high-priority issues while being profitable for the selling organization.

So how can salespeople and their managers increase win rates and reduce stalled deals? The short answer: evidence-based judgment calls about which opportunities to pursue.

High-Probability and High-Profitability Opportunities

Any opportunity worth pursuing is anchored to a customer business priority. If the customer or salesperson cannot articulate the business problem or strategies that the solution must address, the customer probably won’t have much urgency to buy. However, assuming an opportunity is mission critical for a top business issue or priority, the salesperson must understand how the customer defines value.

In other words, salespeople must be able to define the opportunity—the “deal”—by articulating:

  • What the organization is trying to accomplish
  • The customer's main criteria

. . . and then answering these questions:

  1. Will the customer buy something?
  2. Does this opportunity have value for me and my company?
  3. Will the customer buy from me?

A “Yes” answer to each of these is good news—it’s time to pursue! One or more “No’s” should give pause. And, the earlier salespeople can answer these questions in the sales process, the more likely they are to invest their valuable time and resources only on high-probability and high-profitability opportunities.

So how do salespeople find answers to these questions? Read on!

1. Probability Analysis: Will the Customer Buy Something?

Probability largely rests on the strategic importance of the initiative to the customer’s business. Never equate an RFP with a strategic initiative; the customer may just be fishing. Sometimes salespeople can get a sense of the relative strategic importance of the purchase from online research, annual reports, and what the customer organization and key stakeholders post on social media. Other times, salespeople will learn this information through dialogue with their key contact and other stakeholders.

Regardless of the source, salespeople should gather evidence of the initiative’s importance beyond one or two people’s opinions. Every sales professional has seen a customer with a “pet project” they’re personally passionate about—but one that goes nowhere.

Another key probability indicator is whether the customer organization has a level of urgency or a compelling event pushing them toward a buying decision. Little will get done without at least one of these—the opportunity will stall and the salesperson will invest a lot of time and energy that, ultimately, leads to no decision.

A resounding “Yes” to this question indicates that the opportunity might be well worth pursuing; it’s certainly worth assessing potential profitability and whether the customer will buy something.

If the answer to this question is closer to “No,” it’s time to rethink whether the deal is worth the time and resources required to pursue. While not a stop sign, a “No” can be a speed bump.

2. Value Analysis: Does this Opportunity Have Value for Me and My Company?

Value lies not only in the potential top-line revenue. It also lies in the cost of the opportunity. That includes the salesperson’s, sales executive’s, and support team’s time and expense before the sale—and ensuring the post-sale implementation budget delivers the required margin.

A “Yes” to this question ensures that the opportunity represents business that’s good for the customer and the selling organization. A “Yes” is required to pursue; a “No” indicates that the deal isn’t profitable enough to justify the pre- and post-sale cost.

3. Position Analysis: Will the Customer Buy from Me?

If the salesperson says “Yes” to the first two questions, the next “Yes” must be the answer to the third question: “Is there compelling evidence that this organization will buy from me?”

Answering this question accurately requires the salesperson to objectively assess their position with the buying organization by considering the stakeholders’ perception of them, their offering, and their company.

The salesperson’s position reflects evidence about:

  • How well their offering matches the customer’s needs relative to their competitors’ offerings
  • The value the customer places on their offering
  • Their credibility with all stakeholders
  • Their company’s reputation

Gathering this type of evidence enables the sales team to assess the relative strength of their competitive position. If the salesperson lacks evidence, the entire sales team needs to talk and ask questions, listen, and determine the strength of their competitive position so that their “Yes” to this question reflects reality, not a pipe dream.

Should We Pursue?

By assessing probability, value, and competitive position, the salesperson and the sales manager can confidently decide whether or not to pursue an opportunity.

Having a “No” response to one of the first three questions isn’t a deal breaker—as long as the salesperson is confident that he or she can execute tactics to improve the probability, value, or position, and that doing so is worth the required time and resources.

For example, if their position isn’t as strong as they’d like, salespeople need to review the evidence and decide what they can do to improve it. They might strategically deploy SMEs to meet with customer technical experts and have their own executives meet with executive stakeholders at the buying organization. They then need to determine whether these tactics will increase the possibility of a win to justify the required investment.

Make Judgment Calls Based on Evidence

This evidence-based approach invites dialogue and discussion based on facts, not on wishful thinking or numbers that can (at times!) be skewed to sweeten a sour deal. Evidence that shows the probability, value, and competitive position provides a basis for ongoing, strategic dialogues with the sales manager and the supporting organization throughout the sales process. Ask:

  • “What does the evidence say?”
  • “Do we believe it?”
  • “What else do we need to find out?”

Asking and answering questions like these takes discipline—and strategically points salespeople toward the opportunities they are most likely to win.

And everyone loves a winner . . . of the right business.


1Insights, 2018–2019 Sales Performance Study, https://www.csoinsights.com/blog/highlights-from-the-2019-sales-performance-study/

To learn more, contact Wilson Learning at 1.800.328.7937 or complete the online form.

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About the Author
David Yesford

David Yesford

David Yesford, Senior Vice President of Wilson Learning Worldwide, has nearly 30 years of experience developing and implementing human performance improvement solutions around the world. He brings valuable experience, strategic direction, and global perspective to his work with clients. Mr. Yesford is an active member of the Wilson Learning Global Executive Board, with current responsibility at a global level. Over the years, he has held strategic roles in our core content areas of Sales and Leadership, as well as e-learning and Strategic Consulting. He has also held managing director positions in both China and India. Mr. Yesford is the contributing author of several books, including Win-Win Selling, Versatile Selling, The Social Styles Handbook, and The Sales Training Book 2. He has also been published in numerous business publications throughout the United States, Europe, Latin America, and Asia Pacific. Mr. Yesford frequently speaks at international conferences and summits, focusing on issues such as sales and sales strategy, leadership, employee and customer engagement, brand, and strategy implementation.

Read more by David Yesford

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