3 Keys to Making the Most of a New Connection

About a year ago, I made a note in my notebook that I wanted to get better at getting to know people and asking good questions (see my post on my notebook here). A year later I have made some observations, and through much trial and error I have found 3 keys to making a great connection.
Don't ask people to share their best
Don't ask vague questions
Do ask follow-up questions
Don't Ask People to Share Their Best
Often times when first meeting someone, we ask, "What is your favorite ____?" "What is your best ____?" "What is your worst ____?" It seems to me that these are typically counter-productive. Instead of opening up a conversation, they are one of the quickest ways to shut it down.
These types of questions are hard to come up with answers to on the spot. People feel pressure to figure out the best answer and generally end up giving some half-hearted answer, saying "That's a good question. Let me think about it" and never really answering it, or just giving up immediately.
These types of questions can be useful once you get to know someone, but they are difficult to answer in new environments, under time constraints, and when awkward silences are feared.
Don't Ask Vague Questions
Another common question goes something like, "So, what do you do for fun?" or "What are your hobbies?"
I do not want to say that there is never a situation where you should ask one of these questions. However, be intentional when you ask them.
These can again create pressure for the person to come up with something that sounds good in the environment. To truly get to know someone, it is better to hear their story than about things they do.
There is a fine line between vague questions and open-ended questions. The distinction is that vague questions are hard to initially answer. When you ask vague questions, it is hard to pick out a place to begin answering. There is so much to choose from.
You want to ask open-ended questions which are specific and easy to find an initial answer to, but also have a lot of potential behind them. Give your connection a way to start sharing who they are through a specific and open-ended question.
Do Ask Follow-Up Questions
For some reason people have the tendency to jump around from topic to topic hoping something will stick when they first meet someone. They keep from lingering on any topic too long for fear of running out of material.
I have found that I can learn so much about a person through a good follow-up question. For instance, if we begin talking about their job, I might ask if they enjoy it, whether the industry is changing, or how they came to have that job.
These are all questions that are not very intimidating and easy for someone to answer. Although they are simple, they are open-ended which allows someone to tell a bit of their story. Hearing their story makes it easier to ask pertinent follow-up questions after that.
Instead of staying with surface level questions that no one will remember the answers to, these give you a deeper insight into who the person is, what they value, and how they make decisions. As long as you are polite, it also is non-intrusive because it allows the person to talk about themselves and share the parts of their story that they are comfortable sharing with you.
Final Thoughts
It can be intimidating to initiate a conversation. However, in the past year, I have never regretted trying to get to know someone. Sometimes you will have better success than others, but these strategies have lead to me making new friends, business acquaintances, and even just getting a different perspective from new connections.
Be bold in initiating conversations and courteous in your conversations. I have no doubt that you will learn more about the people you come in contact with and enjoy the interactions.
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