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Is Asking the Tough Sales Questions Mean, Or  Merciful?
Blog / For Sales Pros / Nov 15, 2017 / Posted by Robert Jolles / 5334

Is Asking the Tough Sales Questions Mean, Or Merciful?


There’s really no way to sugarcoat it. It is the most challenging aspect of a salesperson’s job–or for that matter that of a parent or anyone who wants to persuade–to ask the more difficult questions. Such questions are sometimes referred to as “pain” questions. Two weeks in a sales training class will show you that it all comes down to this: Are you able to create pain without creating conflict?

Recently I received an email from a salesperson–someone I know, have coached, and deeply respect. In her email she informed me that she had just utilized those “pain” questions with a client, with great success. She revealed to me, though, that forcing her client to examine the most difficult aspects of his resistance to change caused her to “feel a little mean.”

Her revelation stopped me cold. It made me take a deep breath and swallow hard, for I had to accept the fact that I hadn’t fully done my job with this person. In fact, I’d failed to get across the most important lesson I could ever teach her. When you force someone to answer a difficult question – a question that makes another person feel the pain of not taking action, you are not being aggressive. You are, in fact, being empathetic.

I’ll go a step further. I firmly believe it’s one of the most sincere acts of kindness you can offer another human being. We’ve all seen people who are struggling at home, or at work, and we want to help them. Anyone can come to the rescue with his or her wonderful ideas on what another person should do. It never creates change, but it’s a comfortable conversation. I’m talking about taking the tougher road, but ultimately, the much more successful road.

It hurts to be asked by another person what room the children are in when they are fighting with their spouse, but the answer can lead a couple to therapy. It hurts to be asked what impact not supporting a corporate directive could have on a new, starry-eyed manager, but the answer can save a career.

I want people to understand that the process of persuasion isn’t ruled simply by a tactic. It must be accompanied by an emotion. That emotion is one of empathy. You have to believe in the tough questions you ask, and then you will succeed. You’ll succeed in the art of persuasion, and you’ll succeed because you are exemplifying the art of caring about another person. When you ask difficult questions, it is never mean. It is compassionate and possibly life changing. Once confronted with the tragedy so many endure because of their inability to make tough decisions on their own, you see that these questions are, in fact, merciful.

In the end, you get to save things. You get to save both people and businesses, because the path you took required discipline and courage. The results you initiated changed another person’s life. You were the one who helped someone move past his or her fear of change, and into the future. Doing something like that is never mean. It’s quite the contrary. It is something to be proud of.

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About Author

A sought-after speaker and best-selling author, Rob Jolles teaches, entertains, and inspires audiences worldwide. Rob draws on more than thirty years of experience and his keynotes and workshops are in global demand, including companies in North America, Europe, Africa, and the Far East.

Author's Publications on Amazon

Persuade, Don't Push! Surely you know plenty of people who need to make a change, but despite your most well-intentioned efforts, they resist because people fundamentally fear change. As a salesman, father, friend, and consultant, Rob Jolles knows this scenario all too well. Drawing on…
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How to Run Seminars and Workshops is the classic guide for trainers and presenters in any industry. Packed with clear advice and real-world practicality, this book covers all aspects including planning, setup, delivery, coaching, and more—including valuable guidance on selling your services. This new Fourth…
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The Way of the Road Warrior offers weary business travelers inspiration, advice, and practical skills for conquering the competition while conducting business on the road. This business traveler handbook is written by Robert L. Jolles salesman, consultant, professional speaker, and veteran Road Warrior who has…
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Whether you are presenting a product, giving a press conference, interviewing for a job, addressing an audience - you are selling. Selling is about persuading, and you have to think fast on your feet to be adept at it. As one of the most popular…
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This revised edition of Robert Jolles's classic book on sales technique features brands new material throughout, including illustrations, teaching aids, coaching techniques, and true implementation strategies! When you have a process, you have a way of measuring what you are doing. When you can measure…
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For some, projecting confidence and credibility is second nature. For others, it seems like a foreign language they'll never learn – until now. Rob Jolles delivers down-to-earth solutions for anyone looking to enhance the most basic need of all; to be believed. He leverages his…
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