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Asking the Hard Questions

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Why do agents avoid asking the tough questions? Some agents are just not experienced enough to know what questions to ask and will learn in time. However, some agents have an issue called conflict avoidance. We are raised to not create conflict. Realize that the problem is with you and it has nothing to do with hurting your prospect’s feelings.

So why ask the tough questions? Your job is to uncover an emotional need. Emotions sell. Logic does not. People buy on emotion but are moved to action by logic. We have to provide an emotional justification so they will make a logical purchase. Even those who say they buy logically do so because of how that makes them feel. Asking the hard questions creates conflict, and conflict is necessary before someone will change. If the status quo is comfortable, then people will tend to wait to make a decision. They must feel the loss before they will make a decision.

How do you ask the tough questions?

  • Ask with an attitude of a sincere desire to help. People can tell the difference between phoniness versus sincerity.
  • Have an attitude that you’re supposed to ask the tough questions, because no one else has cared enough to ask the hard questions.
  • Ask for permission to be frank. “Mr. Jones, can I be frank with you?”
  • Use third-person stories to get the hard points across. Refer to examples.

A good setup question is: “Has anyone ever gone over this information with you so that you could understand it?”

Here are some follow-up questions that may help you drill down to the real emotions related to their answers. “How does that make you feel?” or “Why is that important to you?”

What are some of the tough questions


  • “Mr. Jones, at the end of the month, is there more month left over or more money left over?”
  • “Mr. Jones, if you passed away today, what would happen to Mrs. Jones financially?” (Note: A loss of one Social Security check, reduced pension or loss of pension altogether could cause a serious living adjustment.)
  • “Mr. Jones, what if you had a stroke today, and had to spend an extra $2,000 a month for home care? Where would the extra money come from?”
  • “Is there a chance you will outlive your money? Who will take care of your bills and living expenses when you run out of money?”
  • “Are you happy with the returns that you’ve received, especially after paying taxes on them?”
  • “If you’ve experienced losses in the market, how has that affected your retirement plans?”
  • “How important is it to have safe investments with good returns?”
  • “Have you ever known anyone who has had to ask their children for financial help?” (Use a third-person story to bring this point home.)


  • “Since you’ve not planned for your funeral needs, which child is going to be able to come up with the $10,000 to give to the funeral home, because they will do nothing unless they have the money up front?”
  • “If all the children have to fly in for the funeral, will they be able to afford all the travel costs (hotel, plane tickets, food, etc.) and the time off from work?”
  • “When your spouse passes on, what will you do when you lose one of your Social Security checks, and perhaps a pension check as well? Most likely, the pension will reduce and the lowest Social Security check will go away.”
  • “What happens when your spouse passes, and your income drops due to no or reduced pension and Social Security?”


  • “I was talking to the Meyers, and Don said that all three of his children said that they would take care of both he and his wife. However, Don did not want anyone of his children to have to bathe him, change him or dress him. He felt strongly about having professional caregivers do those things for him. Do you feel the same way?”
  • “What happens when you use up all of the savings for your care, and your spouse has nothing left to take care of herself?”
  • “I spoke to [customer name], and he shared that he had been married to [spouse name] for almost [X] years. He had been taking care of her for all these years, and he wasn’t about to stop now. Getting a LTCI plan was just another way of taking care of his wife.”
  • “Did you plan early in life to work hard for 30 to 40 years, save all your money, so that you could give it all to the nursing home?”
  • “Sure, no one plans to need care when they get older, and I hope you don’t. I know that you plan to live to be 110 years-old, and die in your sleep. But, what if you’re wrong?”
  • “Why would you risk everything that you’ve worked so hard for, just to save a few dollars of premium?”
  • “Is choice important to you? Why is that important to you?”
  • “Yes, I understand that Medicaid can still take care of you, and you only give all your assets to the government. However, do you think that it will always be this way in the future?”

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