Sales Experts Answer Your Toughest Outside Sales Questions

We asked 3 sales experts to answer 9 of the most puzzling questions in outside sales. Here’s what they said.

There’s a mystique about outside sales. It can seem like rockstar reps are able to close deals like magic, like they never make a misstep. Because of this, many business leaders have questions about outside sales and how to succeed in that field.

Wonder no more, because Base has asked three sales experts to help explain the facts behind how the best of the best maintain that excellence. Geoffrey James is an author and blogger specializing in sales who’s new book “Business Without The Bullsh*t” is available on preorder. Wendy Weiss is president of, as well as a sales trainer and coach. Elinor Stutz is also a sales trainer and author, and she is CEO of Smooth Sale. Here are their answers to some of the most puzzling, toughest outside sales questions.

1. What motivates outside sales reps?

To get the most out of your team in the field, managers and executives need to understand the forces driving their best reps. Building a strong foundation for your entire sales organization is a must, and that first step can improve everybody’s game. So what’s the biggest motivator?

“Winning. Always,” James said.

Simple enough.

2. How do you spend 15 minutes before a meeting?

When so much of success or failure is determined by interactions with customers, reps need to be consistently excellent in meetings. The experts agreed that a quick review was the best strategy. “Outside sales reps should have already done considerable research on the prospect they are about to meet,” Weiss explained. “Use the 15 minutes before the meeting to review your notes.” James concurred: “Review your goal for the meeting and the general questions you’re going to ask in order to reach that goal.”

Stutz offered some offline insights for pre-meeting prep. “Look for awards, letters from clients, specialty magazines,” she said. “See if high-end artwork decorates the walls or motivational posters. Use any of these topics as small talk opening conversations.” Starting off on the right foot can keep you calm and in the zone through the entire meeting, so flex those observational skills.

3. What are your best coaching tips for outside sales reps?

“My No. 1 coaching tip for outside sales representatives is to ask good questions,” Weiss said. “No. 2 is to listen to the answers.” The ideal combination of communication skills means that a rep can zero in on what their prospective client needs and determine exactly how to deliver it.

“Be yourself!” was Stutz’s advice. “Authenticity shines through above those who use ‘the usual.’” Sales pros need to quickly establish a bond with their potential customers, and personality can go a long way toward making a rep memorable.

4. What traits should a great outside sales manager or rep have?

For the best in outside sales, it may come as a surprise that silence is golden. “The ability to keep his or her mouth shut during a sales call and then provide helpful coaching afterwards,” James said of top manager traits. “The patience never to intervene unless the salesperson actively asks for help.”

Weiss agreed on the rep side, too. “The ability to shut up and listen will go a long way toward helping an outside sales rep be successful,” she said. “Selling is a communication skill, and like any communication skill, it can always be improved.”

Stutz weighed in as well. “The best trait is a willingness to learn, observe and learn – and incorporate only that which rings true into one’s own style again to come across as authentic,” she said.

5. What is the hardest part about closing a deal in outside sales?

“Summoning up the courage to ask for the business, even though if the answer is no, your dreams will come crashing to earth and you’ll have just wasted all that time developing the account,” James said.

Closing, the final stage, certainly is the most nerve-wracking. Despite the high stakes, reps have to call on their own confidence in the relationships they’ve built and the products they’re selling in order to seal the deal.

6. How should you go about writing a script for outside sales?

Stutz and James both voiced skepticism about scripts. “Scripts are not natural and reactions to them are all over the map,” Stutz said. “If you want consistency, develop your own style.” If the script is all that a rep knows, then they’re destined for failure. Don’t let them become parrots reciting lines.

Weiss explained how, when used correctly, scripts could serve as both a guide and a learning tool for reps. “There are certain questions and/or objections that sales representatives know they will hear,” she said. “It is vitally important to be able to respond well.” She suggested using the most common questions to prepare for meetings and inform pitches. “If there are questions or objections that you hear all the time, think of ways that you can preempt them by bringing up that first,” she said. “Bringing up the issue first puts up in control and allows you to frame it in the best possible way.”

7. How should you measure ROI of your outside sales team?

“Actually, I think the term ROI has become a bit buzzwordy and I’m not sure what it really means in a lot of cases,” James said. “I’d probably say compare your cost-of-sales to other companies in your industry. If it’s a lot higher, your ROI is screwed up.”

As he explained, it’s crucial to understand not only what metrics your team is measuring, but why. Make sure that the data you track makes sense for the type of business you run. Find numbers that will give an accurate reflection of your company’s health and bottom line.

8. What are the best books for outside sales reps and/or managers?

Our experts are all prolific authors, and each of them has more valuable insights to share with reps. One of James’ books is an intro to the trade called “How to Say It: Business to Business Selling.” Weiss’ book is titled “The Sales Winner’s Handbook: Essential Scripts & Strategies to Skyrocket Sales Performance.” Stutz wrote “Nice Girls DO Get the Sale: Relationship Building That Gets Results.”

In addition, Stutz mentioned the time-honored classic, “How to Win Friends and Influence People,” as well as “No Bull Selling.” Weiss recommended “Unlimited Selling Power: How to Mastery Hypnotic Selling Skills” by Donald Moine and Kenneth Lloyd and “Influence the Psychology of Persuasion” by Robert B. Cialdini. James has written about sales books before, and suggested titles such as Neil Rackham’s “Spin Selling.”

9. What is the best compensation model you’ve seen in outside sales?

“I’d say a combination of 1) customer satisfaction, 2) revenue booked, and 3) strategic sales (like big name customers who might become reference accounts),” James explained. “Mostly it shouldn’t change much.”

Remember, your reps are motivated by winning. Whatever model your business uses, make sure it reflects and rewards those who are successful at staying on top.

What other questions do you have about outside sales? Leave a comment and we will do a follow-up post.

We were recently named one of 18 Sales blogs to follow in 2014 by Sales Engine!

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