There’s no sugarcoating it:  The most challenging part of the job of a salesperson, a parent, or of anyone who wants to persuade, is to ask the more difficult questions.  These are the questions that are sometimes referred to as “pain” questions.  If you spend two weeks in a sales training class, you know that it all comes down to one thing:  Can you create pain without creating conflict?

I recently received an email from a salesperson I know; I have coached this person and I also deeply respect her.  In her email, she told me that she had just asked some of those “pain” questions to a client, and successfully, I might add. The process of forcing her client to look at the most difficult aspects of his resistance to change, however, made her “feel a little mean.”

Those four words made me stop what I was doing, take a deep breath, and swallow hard.  At that moment, I had to accept the fact that I wasn’t doing my job.  I hadfailed to teach this person the most important lesson I could ever teach her.  When you force someoneto 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 sympathetic.

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.  If you truly believe in the tough questions you ask, 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’squite the contrary.   It is something to be proud of.