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Overcoming The Top Selling Challenges of 2019

Exploring Today’s Top Sales Challenges

Richardson’s annual research study of sales professionals across industries offers ground-level insights into changes within the sales environment.

The responses revealed that changes in the business environment are demanding new selling skills. Sales professionals need to be agile. They need the ability to transition from one skill to another as they encounter different challenges. That is, they need to deliver different value propositions across various stakeholders, each with a unique perspective. Success today is about knowing when and where each skill needs to be deployed. The customer’s needs and perceptions change throughout the buying process; therefore, the sales professional must adjust accordingly.

In 2019 successful sales professionals will be able to read each selling scenario and fine-tune their approaches in the moment.

Executive Overview

We surveyed over 300 sales professionals to identify their anticipated sales challenges in 2019. This report provides the top answers to our questions across multiple categories of selling activity. We also deliver our insight into how best to address each of the top challenges.

The most pressing challenge for sales professionals is the increased complexity in selling today. It is no longer enough to rely on one skill. Success now requires managing multiple touchpoints even within one selling opportunity. Sales professionals need to consider how they will maintain a consistent cadence across multiple channels, overcome the buyers’ misperception of what they need, and build allies within the customer decision-making team. A growing sense of uncertainty and unpredictability means that selling now demands balancing between an appeal to logic and emotion.

The second most pressing challenge at 26% was “understanding how to create competitive differentiation,” indicating that many solutions today offer a breadth of features and customization that make it difficult to stand out from other options. Moreover, customers are often already familiar with many of a solution’s features and benefits through their online research.

The third-largest response at 25% was “consistency in executing meetings as an effective team,” illustrating the emerging need to present cohesively in front of multiple stakeholders and seamlessly transition to and from a subject matter expert, as needed.

These responses show that sales professionals need the ability to pair the right selling skill with the right challenge. With agility, sales professionals can quickly flex and adapt in ways that respond to the sale in real time.

Here we examine the survey results in greater detail.

top sales challenges


Customers today face competing priorities. Therefore, sales professionals are discovering that it is getting more difficult to get the customer’s attention, especially in the initial outreach efforts. For this reason, “gaining appointments” ranked as the top challenge facing sales professionals in their prospecting efforts. Part of the customer’s reluctance to engage sales professionals may stem from indications that a less bullish economic environment lies ahead. Additionally, gaining an appointment often entails aligning numerous schedules, as multiple stakeholders are involved in the buying process today.

The second and third highest responses of “getting to the right stakeholder” and “maintaining a consistent cadence of contact across multiple channels” illustrates the fractured nature of selling in today’s market. Multiple decision-makers each have their individual set of priorities and internal demands. Getting these disparate groups to coalesce is an increasing challenge. Sales professionals struggle not only to align schedules but also to address a growing list of needs as the stakeholder count rises. Some sales professionals meet this challenge by engaging buyers in a virtual setting like Zoom or Skype.

Lastly, the prospecting challenge “creating a targeted prospecting strategy,” which was the top challenge in 2018, was not part of the top three challenges in the 2019 study. This change might indicate that sales professionals have access to a plethora of prospecting tools and instead face challenges in getting those tools to have the intended effect.

prospecting challenges

Uncovering Client Needs

The top challenge cited by respondents was “creating value and insight during the conversation with the client.” This was the second most frequent challenge indicated by survey participants last year, suggesting that it is getting more difficult to deliver ideas that resonate with buyers. Meaningful insights can only develop when the sales professional has a deep understanding of the customer’s industry and business and the emergent challenges they need to overcome.

“Overcoming buyers’ misperceptions of what they need” was the second most cited challenge, moving up from the third-place spot last year. These misperceptions often stem from the customer’s online research, which can complicate, obscure, and misdiagnose the problem. Overcoming the buyers misperceptions is a challenging endeavor. Sales professionals must be careful not to offend the stakeholders while, at the same time, shaping their perceptions.

“Exploring client issues and challenges to define the strategic impact of your solution” made its way into third place, up from fourth place last year. Sales professionals are discovering that customers are more guarded and less willing to share their strategic drivers to those who haven’t earned the right to ask.

understanding customers


“Maintaining profitability” was the top challenge for sales professionals. This challenge has replaced last year’s top response, which was “gaining higher prices.” Sales professionals are feeling the pricing pressure as more solutions become commoditized.

Like last year, the top three challenges are connected to pricing concerns, as sales professionals cite “working with clients who continue to reopen the negotiation/more concessions” and “gaining higher prices” as the second and third highest-rated challenges respectively.

The customer’s tendency to reopen negotiations reconfirms the notion that negotiations are an ongoing process. This characteristic of selling today is often due to the multiple stakeholders involved. Sales professionals are working to overcome objections and demands across a variety of decision-makers.

These factors mean that “gaining higher prices” is a serious challenge. Many businesses are becoming less optimistic about future economic conditions and are therefore reluctant to absorb risk. Gaining higher prices represents the dual challenge of getting customers comfortable with a buying decision and getting them to expand the financial scope of the sale or see its full value.

sales negotiation challenges

Buyers Decisions

The status quo has deep roots. “Building a case for change” and “combating the status quo” were two of the top three responses. Customers continue to be reluctant to change their current states. As the pace of business intensifies, buying decisions are getting sidelined as leaders struggle to hit the revenue goal for the quarter or the year. Even if the customers see the value in the solution, they often fear the burden of implementation and adoption that distracts from the growing list of daily responsibilities.

challenges in buyers decisions

The second most frequent answer to the question was “comparing their options.” The nature of business challenges today is more complex than ever. This complexity leads to fractures among the stakeholders. Each has a different way of defining success. Each is accountable for different outcomes and therefore will see the issue in a different way. Just the initial step of defining the challenge is a considerable hurdle, which makes comparing options even more challenging.

Last year, “securing budget” was one of the top three responses to this question. This year, more sales professionals are struggling just to reach this phase of the selling process. Selling today means more than outperforming competing sales professionals because the competition is often an abstract feature like fear, ambivalence, complexity, and routine.

Managing Accounts

Growing key accounts is an ongoing challenge. Sales professionals are recognizing the difficulty of “becoming a trusted advisor” to businesses facing revenue goals and shifting internal priorities. This challenge was the most cited in response to the question of expanding relationships. The responses from last year echo this sentiment, given that sales professionals selected “balancing sales and relationship management” more than any other response in 2018.

The struggle to become a trusted advisor is characterized by challenges in “finding ways to add relevant value for various stakeholders” and “balancing sales with relationship management,” the two responses tied for second place.

Adding value and becoming a trusted advisor requires customer insights that go beyond what the stakeholders have learned on their own.

This base of knowledge leads to different definitions of value across the buying group. A solution has a different value proposition for a CEO than it does for the CMO, CHRO, or even the procurement specialist. The number of minutes sales professionals have in front of these different buyers is shrinking. Therefore, each interaction must add value beyond a list of product features. If the sales professional becomes an active participant in the struggle to solve a business challenge, they will become a trusted advisor.

challenges managing sales account

Selling Skills

As so many of the previous questions indicate, “delivering a compelling value proposition” is the most valuable selling skill in 2019. Previously discussed answers like “creating value and insight during the conversation with the client,” “building a case for change,” and “finding ways to add relevant value for various stakeholders” all trace back to delivering a compelling value proposition.

A meaningful value proposition is rare in a business landscape characterized by commoditization. Quality is not the selling feature it once was. Customers assume all solutions offer quality, and they want more for their business. A resonant value proposition takes these factors into account.

Even a compelling value proposition is not enough; sales professionals need a way to convey the message. They must consider concepts like germane load, which refers to the amount of interpretation the message requires. Messages that require interpretation will not resonate or stick. Make the decision process easy for the customer. Customers are pressed for time and are under pressure. They need memorable messaging that can be absorbed effortlessly.

Respondents also made it clear that asking insightful questions is a valuable skill. This makes intuitive sense, given that the answers to these questions help shape the value proposition.

Unpredictable Markets

Buyers have less certainty about the broader economy. These concerns arise from increasing volatility and shortening business cycles. Some respondents are seeing this phenomenon firsthand, citing “unpredictable market forces.”

Some businesses are already responding to this uncertainty with “reduced income and related budget cuts.” This trend is a concern for sales professionals who have indicated that customers fear a “potential economic slowdown.” A consultative approach to selling works in this environment because it tracks the changes as they unfold. Consultative selling moves with the customer.

Gaining Access to Senior Stakeholders

Sales professionals continue to struggle in their attempts to reach senior stakeholders. With so much focus on pricing, sales professionals often face procurement specialists first. This challenge means that factors like cost become frontloaded in the dialogue. As a result, the sales professional doesn’t have as much opportunity to ask questions, deliver insights, and develop a customized value proposition.

Gaining access to senior stakeholders begins by building a foundation for the request. The most effective way to do so is to draft a value statement that addresses the relevant issue, action, and value. The issue summarizes the customer’s goal or challenge. The action explains how the solution will meet the customer’s needs. Finally, the value must answer the question “So what?” What are the positive outcomes the customer can expect? The more specific, the better.

Increasing volatility has renewed sensitivity to risk among customers. Therefore, sales professionals need improved agility, which is the combination of skill proficiency coupled with an understanding of how and when to use these skills throughout the twisting road that is the buyer’s journey.

Getting the customer’s attention is as difficult as ever. Often, customers view a business purchase as a burden on their time and an exposure to risk. This characteristic of selling today reinforces the idea that sales professionals need deeper insights and a more customized value proposition to uproot customers from the status quo.

Moreover, the power of a strong value proposition is doubled by the fact that it serves to protect or even increase the financial value of the sale.

At Richardson, our approach to helping our customers solve these challenges is to build sales skills through our Connected Selling Curriculum™. The curriculum is a collection of sales training programs built to work together and build upon each other across roles and capabilities to drive a common language and clear approach for sales performance at scale. Contact us to learn more.

About The Author: richardsonsalestraining
Richardson is a global sales training and performance improvement company. Our goal is to transform every buyer experience by empowering sellers with critical skills so they can create value to buyers and drive meaningful conversations. Our methodology combines a market proven sales and coaching curriculum with an innovative and customizable approach to learning that ensures your sales teams learn, master, and apply those behaviors where and when it matters most — in front of your customers. It’s our job to anticipate change in your industry so that your sales team can focus on fostering long-term relationships, becoming indispensable partners for their buyers.