Top 10 Challenges for Salespeople

A lot can be said about today’s selling landscape, but the most accurate description? Noisy. Old ways of selling may no longer reap results. To push out information and hope it sticks likely will no longer work. You have to get personal, tell a story, be memorable and, some would even say, become vulnerable.

“We are currently operating in a time of rapid business disruption, marked by constant change and unpredictability, and a tremendous amount of noise,” says Lance Tyson, president and CEO, Tyson Group. “For salespeople, the digital era is full of starts and stops in their communications with prospects and customers.”

Tyson says that most buyers have a wealth of information at their fingertips, to include product websites and external information available on Google and a host of social media sites. Buyers can form opinions and make decisions in the blink of an eye.

All in all, you need to know your customer. That means knowing what is important to your customer, and understanding how to tell a story that will convince that customer to buy from you instead of someone else.

“Cookie-cutter just doesn’t work anymore,” says Cindy McGovern, Ph.D., CEO of Orange Leaf Consulting and author of “Every Job is a Sales Job: How to Use the Art of Selling to Win at Work.” “Everyone wants a unique experience, and everyone—and everything—is constantly changing. Going into 2020, you need to keep up. We live in a 140-character-conversation world. As a salesperson, you have to sell your customers again and again, in every interaction you have with them. What you did last year isn’t going to work next year.”

10 challenges to face head-on

CANVAS talked with sales-focused thought leaders to learn what every salesperson should expect to face moving into 2020:


1. Buyers have a glut of information at their fingertips

“We live in a world where everyone has a phone full of apps to serve their every need, and devices to measure the value of every step they take and every penny they spend,” Tyson says. “Buyers can now do pricing comparisons with just a few taps, find consumer and peer reviews and other information, and quickly assess the value of a business or service. Suggestive selling is becoming an art form. Salespeople need to build a rapport and help the buyer go through the process, rather than trying to force their decision prematurely.”

2. Do not let a lack of planning become a missed opportunity

“Customers want to be treated as individuals, which means the sales professional needs to get to know each customer’s wants and needs—and what your company has that can fill that need,” McGovern says. “That takes research, preparation and planning. In this day and age, every job is a sales job. When the opportunity arises to get a bit more business out of an existing customer, every employee should be empowered to do it. Customer-facing employees should ask every client, ‘What else can I help you with today?’ before saying, ‘Goodbye.’”

“Customers want to be treated as individuals, which means the sales professional needs to get to know each customer’s wants and needs.”
— Cindy McGovern, Ph.D., CEO of Orange Leaf Consulting


3. Rejection cannot be taken personally

“The key to not taking rejection personally is to never reject yourself,” says John Livesay, Forbes columnist and host of “The Successful Pitch” podcast, and author of “Better Selling Through Storytelling: The Essential Roadmap to Becoming a Revenue Rockstar.” “When you get a ‘No,’ remember it is for now, not forever. Don’t beat yourself up or doubt yourself when you get rejected. Remember who you are is a competent, confident salesperson with a valuable product or service to offer.”

4. The landscape is crowded, and communications are increasingly fragmented

“If emails aren’t getting through in the beginning of the sales process, and LinkedIn is too congested, try sending a note on paper, and then following up with a phone call,” Tyson says. “When communicating with prospects, salespeople are often dealing with an unbelievable mix of conversation fragments coming through a variety of channels, including text, voicemail, emails, phone calls, and more. They need to be agile in their approach and develop the skills to pull all of that information together and advance it forward.”

5. Competitive alternatives are emerging that are more appealing to your customers

“In some industries, product offerings are viewed as essentially being interchangeable, and the consumer does not view them as unique,” says Jill Johnson, president and founder, Johnson Consulting Services. “These types of products can encompass anything from facial tissue to wood products. Consumers often shop for these items based on price. For example, with an item like lumber, consumers are seeking composite lumber alternatives that resolve the issues of maintenance. They are willing to sacrifice some of the quality and beauty found in a traditional lumber product for the easy and maintenance-free option.”


6. Time has become the most precious commodity for most people

“The default process for most salespeople used to be to reach out to a new prospect asking for a meeting or a call,” Tyson says. “But people are becoming more reluctant to give up their time. The most critical skill now becomes either convincing them that you are worth the expenditure of time, or figuring out a way to move things forward without asking them to sacrifice their time.”

7. You do not have to be perfect, but you do have to be memorable

“People relate to people who are vulnerable and transparent,” Livesay says. “Be a ‘progressionist’ who celebrates your progress. To be memorable after you leave a presentation, tell a story that is clear, concise and compelling. A story that is easy to repeat and has an emotional connection will make you memorable.”

CANVAS - Top 10 challenges for salespeople

8. Consumers are influenced by and share opinions on social media

“Consumers look to social media to get opinions about what they should buy and from whom,” Johnson says. “Stay on top of your social media profile, and look at your Star Ratings on all social media platforms. Make sure you have a disciplined approach to monitoring your presence on all social media platforms. Even if there is a glitch, a great response by members of your team handling it can generate a positive comment on social media. This kind of positive commentary is gold!”

9. Good sales professionals must embrace consultative sales

“Leave any remnant of the old, pushy, manipulative sales strategies behind,” McGovern says. “People are naturally suspicious of sales professionals, especially if they detect any sliver of dishonesty or high pressure. The solution for sales pros: Listen with an ear toward discovering exactly what your customer wants or needs. Then, find a product or service that fills that need. Don’t try to sell what you want to sell. Instead, sell what the customer wants to buy.”

“Salespeople need to be able to facilitate conversations in lots of ways,
and bring discipline to the process, even when it seems casual.”
— Lance Tyson, President & CEO, Tyson Group


10. Things often seem deceptively casual

“A text thread about meeting at a coffee shop at some point in the future may seem very casual, but if it’s not handled with a certain degree of formality, it could result in a missed opportunity,” Tyson says. “Salespeople need to be able to facilitate conversations in lots of ways, and bring discipline to the process, even when it seems casual. Some people are naturally good at this, but for others, it requires a conscious effort.”