Your Toughest Outside Sales Questions Answered


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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. 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 outside sales questions.

Published in: Sales, Business, Technology

Your Toughest Outside Sales Questions Answered

  2. Base CRM 2 Meet the experts. ! ! Elinor Stutz Smooth Sale ! Elinor Stutz started the company Smooth Sale to empower business owners to thrive in the competitive market today. Elinor’s motivational and inspiring talks and articles have garnered serious praise for Elinor as purveyor of fresh ideas in the crowded sales landscape. ! Wendy Weiss ! Wendy Weiss is the president of She’s an authority on lead generation and new business development. She has written and contributed to numerous books on all aspects of business, and is known as the Queen of Cold Calling for her focus on helping businesses learn to make cold calls that get results. ! Geoffrey James Sales Source, Inc. columnist ! Geoffrey James authors the popular Sales Source column on Inc. and has written several books, including “Business Without The Bullsh*t” and “The Tao of Programming.” Geoffrey spent 6 years doing market research and product branding for a Fortune 100 company, and his combination of writing, programming, and business acumen make him a go-to expert for sales leaders. !
  3. Base CRM 3 1. What motivates outside sales reps? ! ! ! “Winning. Always.”
  4. Base CRM 4 2. How do you spend 15 minutes before a meeting? ! “Outside sales reps should have already done considerable research on the prospect they are about to meet.” ! ! “Use the 15 minutes before the meeting to review your notes. Review your goal for the meeting and the general questions you’re going to ask in order to reach that goal.”
  5. Base CRM 5 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. No. 2 is to listen to the answers.” ! ! “Be yourself. Authenticity shines through above those who use ‘the usual’.”
  6. Base CRM 6 3. What traits should a great outside sales manager or rep have? “The ability to keep his or her mouth shut during a sales call and then provide helpful coaching afterwards. The patience never to intervene unless the salesperson actively asks for help.” “The ability to shut up and listen will go a long way toward helping an outside sales rep be successful. Selling is a communication skill, and like any communication skill, it can always be improved.” “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,”
  7. Base CRM 7 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.”
  8. Base CRM 8 6. How should you go about writing a script for outside sales reps? “There are certain questions and/or objections that sales representatives know they will hear. It is vitally important to be able to respond well. 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. Bringing up the issue first puts you in control and allows you to frame it in the best possible way.” “Scripts are not natural and reactions to them are all over the map. 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.”
  9. Base CRM 9 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. 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.”
  10. Base CRM 10 8. What are the best books for outside sales reps and managers? ! “Spin Selling” and “How to Say It: Business to Business Selling” “Unlimited Selling Power: How to Mastery Hypnotic Selling Skills”, “Influence the Psychology of Persuasion” and “The Sales Winner’s Handbook: Essential Scripts & Strategies to Skyrocket Sales Performance” “How to Win Friends and Influence People”, “No Bull Selling” and “Nice Girls DO Get the Sale: Relationship Building That Gets Results”
  11. Base CRM 11 9. What is the best sales 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).”
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