One-on-One Awkward Conversation Starters!

Each week I speak with many people. Often I am having a first-time conversation with strangers. It is part of my daily work. I actually enjoy speaking with complete strangers. It is challenging yet fun to engage in these type of conversations. It means thinking on my feet and making the conversation enjoyable for whomever I chat with. 

Most people avoid having conversations with people, especially with strangers. For most it us it is intimidating and produces feelings of dread.

After having hundreds of awkward conversations, I know one thing for sure; leading the conversation with strangers is super weird! I have often have conversations with people who don’t engage in the discussion. The typical one-liner conversations quickly turn awkward. When there aren’t reciprocating discussions or responsive conversations it becomes terribly uncomfortable. (Picture is of my grandkids dressing up and pretending to have adult conversations.)

Questions that often end up as dead-end conversations are, for most, the worst of experiences. How are you? What have you been up-to? How’s it going? These questions and many more like them have the same thing in common. They all end with a common response. Short 1 or 2-word responses: Okay! Nothing! Not bad! Then what do you do?

So, today I wanted to provide a short article on how to have one-on-one awkward conversations the lead to mutually beneficial relationships. There are several ideas that have helped me during these weird exchanges.

1. Instead of asking yes/no questions, ask questions that  require sentence responses.

I have asked many people permission to pray for them. I do this by not asking a yes/no question. I ask, “HOW can I pray for you?” Read further on this topic The key is to assume the affirmative. 

By asking questions that require more than yes/no answers will help engage a deeper, yet meaningful conversation. Of course, you’ll have to consider the circumstances and the timing of the conversation. Just like humor, short stories and quick punchlines our favorites. If someone appears to be in a hurry it is not the time to deepen the conversation. If there is a reciprocating effect that is happening, then you can go deeper. Nevertheless, asking questions that get them to talk about themselves which is more favorable rather than telling them about yourself. In fact, when the conversation ends too quickly we are tempted to talk about ourselves. This is not appropriate, especially at first. 

 

So often, for even the strongest extrovert, the conversation seems to drag and feel uncomfortable. Too often we cut the opportunity short because we feel awkward. I have heard it said which is often associated with Abraham Lincoln; “It is better to remain silent and be thought of as ignorant than to open your mouth and remove all doubt.” Perhaps our greatest fears is that we will say the wrong thing. These present barriers and often an illusion. We perceive these ideas but often they are not true. Most people are just happy that somebody is willing to chat with them and many are gracious spirits that forgive easily if we are intending to injure the relationship. 

As we assume the affirmative it helps us to further the conversation. Starting with a compliment or discovering something about them is often a positive tactic we could use to engage a healthy interaction.

2. Instead of turning the conversation into an interrogation (the 20-question survey), have a topical discussions.

Many times we make conversations a door-to-door sales survey. It is important for you to feel and appear relaxed. Don’t sweat it! Most people can quickly read into our objective especially when we feel like it’s a set up. Too many of us have received those annoying sales calls or high-pressure experiences and if you come across like a used car dealer then it could be a turn off.

I love church signs. The one here is funny because of the huge social media problem we have today. This one reads: “Tweet others as you want to be tweeted.” I like to think of three significant topics that most people like to talk about. These three topics are easy for any of us to navigate. They include talking about them: the most important topic of all. People also like to talk about simple observations. I find that people most often are okay with talking about values, their values. 

Most people love to talk about themselves so start there. Simple question about them or starting with an observation is a good beginning. While it is cliché, starting a conversation with what do you do or how do you do that engages a persons self interest.

Making quick observations about what you see can turn into a good discussion point. Perhaps it’s the current affairs of the day, that which is in the news or if you are at an event, Ask someone how the organization can improve their experience is a good starting point. Never become defensive if they give negative feedback but they simply offering their insights are both helpful to you and them. Sometimes you might observe that they are or have served in the military or you notice a saying on their clothing or some thing that you can complement about them is a good starting point. Think of ways that you can ask questions related to the genre for which you are observing. 

3. Instead of having in-depth discussions, be okay with simple conversations. 

It’s important to lower your expectations at first. Sometimes we expect that somebody would have a deep insight about a topic. Nevertheless it’s important to be okay with small talk. You have to start somewhere when engaging people. 

As you begin any relationship, it is important to let the conversations be relaxing times of interaction. Don’t rush into the relationship because it is built on trust. To have any relational collateral you have to spend time to build trust. 

Say genuine things that help build up relationships. People can easily see if we are sincere or not. So, therefore be real. Be relaxed. Take the conversational cues carefully so that your impact is felt; don’t try to impress people. I love the saying; “You IMPRESS people from a distance but you IMPACT them up close.”  It is my life statement. I have made every effort to impact people. It is not about you!  It is always about the “other.”

Finally, instead of ending the discussion seek permission to talk again.

As you engage and feel a positive response from your interaction, ask for an opportunity to connect further at another time. Seek to serve their needs as you follow up with relationships. 

Asking for permission to further the discussion you have begun may be a simple as saying, “Are you okay with meeting up in the future?” As you put the controls in the hands of those you engage is important. Making the relationship about them is a key to starting and establishing a good foundation for more discussion. 

Read more on this topic here.

Interesting video you may want to check out. How to avoid socially awkward behaviors.