This particular article is about a topic that people seem to have trouble with, which is: “How do I engage someone with a question I’ve asked a thousand times?”

I don’t know about you, but I’m bored of answering the same questions over and over again. However, there is a really simple answer, but as always the execution can be difficult.

In general, the way people are is that they have been asked some of the same questions all their lives. Sometimes these questions are phrased slightly differently, but still have the same boring impact. These questions are generally generic and do not elicit an emotional reaction from people.

Examples of these types of questions are:

“What is your passion in life?”

“What kind of hobbies do you enjoy?”

“What is your job?”

“Tell me about you?”

The weird thing is that these questions on their own are pretty brilliant, but if you can ask them in a way that a person has never been asked before, it will help make the conversation even easier. This is part of what charisma is.

Imagine if someone had told you that a piece of chocolate cake I had was good. Now imagine that the same person said it was delicious. So he decided to use the word delicious to describe the taste of this chocolate cake.

The third sounds much better because we don’t use the word “delicious” in our daily conversation, and yet it still conveys the message that the cake was delicious but in a way that produced a guilty pleasure. The word delicious is what I would call a “novelty word”. A word that most people understand, grabs the other person’s attention, but is rarely used.

The questions are no different. So you want to think of a way to ask a question, but phrase it differently so that it becomes a refreshing new question.

Passion in life – “If you weren’t in the career you’re in now, what would you like to do?”

Hobbies: “So what are some of the activities you do that make life more enjoyable for you?”

What do you do- “Don’t tell me your job title, but tell me what your favorite part of your job is right now?”

Take the time to think about all the questions you might be asking, but rephrase them in a more interesting way, and see how many more people will want to engage in conversation with you.

Everyday questions can be interesting, but you have to use your imagination. A general rule of thumb when meeting new people at a party, business function, or any event is to say… “Would I like to be asked this question?” And if you don’t, don’t ask.

Here is your personal challenge. Think of a question you’ve been asked hundreds of times, take that question, change the wording, and then test the question on people. See what kind of reaction you get and the questions that work, stick with them. The ones that don’t seem to be effective, you can throw them in the trash of the conversation.