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I may be wrong but I assume people are described as difficult mostly when they talk too much or with sudden changes of topic, not when they talk/ask too little. I certainly don't know if this is true in your case, but you may want to focus more on (active) listening rather than your focus on questions. So I want to ask people questions that will please ...


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Adding to the previous responses, reflection is a great tool to use in all conversation. A great resource to fully understand reflection and its uses is: Motivational Interviewing: Helping People Change, 3rd Edition (Applications of Motivational Interviewing) by Miller and Rollnick I have had similar challenges as described by OP and this book provided ...


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In my experience, its easy to think that every question you ask someone in a conversation needs to be an amazingly clever, insightful, etc. question, which is generally not the case. Often, the questions that get people to share more, and feel like they are listened to, are simple questions that show that you're interested in what they are talking about. ...


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