How to Ask the Difficult Questions

One of the many rewards I receive from interviewing people for their LifeStories is the gratitude from the children and grandchildren of the interviewees. One of the things they typically say is, "I've known them all my life but have never heard that story before." One of the reasons why they've never heard the story is because they never asked the question. The most common reason for not asking the question is because it is a difficult one to ask. Here are my thoughts on asking those difficult questions you've waited a lifetime to ask: Thought #1 - Ask the Question Anyway - "How do I word the question?", "When is the best time to ask it?", Where should I ask them that question?" are all real fears that get in the way. I say, "As the question anyway." The fact that you are concerned with those points should let you know that you are sensitive to the subject. If you let fear, however, get in the way of your asking the question, it will never be asked. All too often, I'll hear at a funeral, "I never knew _____ about them." If you don't ask, you'll never know! Ask anyway.

Thought #2 - Use Empathy - Think to yourself, "If someone were to ask me the same question, how would I want it to be asked of me?" Whatever the answer to that is, use it to ask the question. This is how I formulate many of the questions I use in the LifeStory interviews I conduct. If you follow this advice, your caring and concern for the other person will shine through and make their answer as genuine as it can be.

Thought #3 - They've Been Waiting for You to Ask the Question for a Long Time - While this idea might seem foreign to you, you'll be surprised when they tell you, "I knew you were going to ask me that. I just didn't know when you were going to get around to it." The amazing thing about this is that the've had an answer for you in their mind for a long time. Think about it in your own life experiences...some things you are just not going to volunteer to tell people unless and until they ask. But when they ask, you will gladly answer. It's true!

Thought #4 - Approach the Question with the Benefit of Others in Mind - Here's an example of what I mean by that: "I know you went through a divorce in 1968. Please share with me what experiences you went through and what lessons you learned from those experiences so others (substitute here "your grandchildren", "your children", "I", etc. instead of "others" if it fits) will not go through the same difficult times as you did." Remember, everyone goes through difficult times in life. Most people would be happy to share those experiences if it means being able to help others avoid making the same mistakes they made.

Thought #5 - Sincere Interest and Genuine Curiosity - I've mentioned this before and cannot emphasize it enough. Questions about someone's life should always be asked with sincere interest and genuine curiosity...and you cannot fake either! This is especially important when you ask difficult questions. The person you are asking will see this and will more likely respond favorably.

Be sure to give yourself a pat on the back when you ask those difficult questions. It's a brave thing you are doing and you should reward yourself for doing so.