Ask These Two Questions To Get Past Small Talk

Are you ever having a conversation with someone whom you want to get to a deeper level of conversation but you can’t get past small talk?

Maybe it’s someone you know, and you can’t seem to get beneath the surface. Maybe it’s an employee on your team and sometimes you are at a loss of how to get them to open up without appearing invasive. Or perhaps you find communicating with introverts difficult because they are so quiet.

There are a couple of questions you can ask that will take you to a deeper level of conversation. These questions are like green lights–letting the other person know you want them to share their experiences or thoughts with you. You will likely notice an increased feeling of energy from the other person when you ask them these questions. And introverts will appreciate these questions, as they generally hate small talk, and long to get to a deeper level of conversation when communicating with people they like.

Because authenticity is paramount, I do not recommend asking these questions to manipulate or flatter someone. Only ask them when you truly care about the person you’re communicating with and desire to get to a deeper level with them. And remember–when you ask these questions, you have a responsibility. A responsibility to truly listen rather than to think about your next question or your next answer.

Here are two questions you can ask that can keep a conversation going and take it to a deeper level:

1. “Can you tell me more about that?” or “What’s the story behind that?”

Once someone has shared something with you, there is probably more to the story. And all you have to do to get the “back story” is to ask, When you ask this question, you are relaying to the other person that you want to hear more from them. And when you use the phrase, “tell me more…” or “what’s the story…” you will find that they will share a lot more than they did initially, because you’ve given them the green light that you want to listen. As an introvert, I love asking this question because it results the person going beneath the surface, and I love it when someone asks me this question, because I tend to give brief answers until I know that someone really cares to listen to what I have to say.

2. “Can I get your thoughts on something?” or “Can I get your opinion on something?”

This is an amazing question that can actually cause people to immediately answer with a “yes”, and lean in to intently listen to what it is you want to ask them. Why? Because when you ask someone their thoughts or opinions or advice, you are essentially acknowledging that you value them. It’s like giving a compliment, but with a different twist. I was at a dinner function, and had been in conversation with a woman I know sitting next to me. We had been talking “small talk” for awhile. I asked her, “Can I get your thoughts on something?” She immediately nodded with affirmation and gave me her full attention. Right about that time, we were interrupted by someone who was passing by our table and started a conversation. Once the long interruption ended and the person walked off, I decided to not bring up the question again, but she turned to me and said, “now, what was it that you want my thoughts on?”

Ask these questions in both your personal and your professional life when you want to get to a deeper level with others. You will only gain new insights from them, but your relationships will become stronger as well. And that is what great communication is all about!

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