Don’t be a chicken.

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I cannot stop listening to conversations around me. Most people call this eavesdropping, but I call it research. My best estimate is that 90% of conversations are carried out at a very superficial level. In other words, typical conversations follow this model…

John: “How was your week?”
Sally: “Not to bad.”
John: “Anything exciting happen?”
Sally: “Not really. Just work. I did start reading a new book.”
John: “That’s nice. Have you seen any good movies lately?”
Blah, blah, blah, blah… Oh, and yada, yada, yada.

I have overheard 90-minute conversations at the table next to me in a restaurant that had no more substance than the short conversations with their server. Some of the blame for these superficial conversations falls on smartphones, smartwatches, and every other piece of “smart” technology that you carry with you everyday. Most people are more concerned with the notification that just popped up on their phone than with the human being sitting in front of them.

Recently, a study was conducted that discovered having a phone on the table during a conversation lowered the perceived quality of the conversation as well as the connection felt between the two people. The interesting part of this study is that the phone did not even have to belong to either of the two people holding the conversation… the anonymous phone simply had to be present. When the phone was not on the table, the conversations received a higher perceived quality score and the connection between the subjects was rated as being stronger. If an anonymous phone simply sitting on the table negatively impacts a conversation, imagine how much life your personal phone drains from your conversations.

My first (and very easily accomplished) piece of advice to having deeper conversations with others is to put your phone on “do not disturb”, turn the volume off, and put your phone out of site of everyone involved in the conversation… including you. I promise that you will not die when you do this. It may, however, cause you some anxiety. This anxiety will diminish as you make this a normal practice. What this anxiety is telling you is that you are addicted to your phone. I am not using the term “addicted” as a metaphor. The anxiety you feel is similar to the anxiety that smokers feel when attempting to stop smoking or that alcoholics feel when quitting the booze or a chicken feels when it does not receive a food pellet when the blue light shines. Don’t be a chicken. Put the phone out of sight.

With your phone out of the picture… literally, the blame for a superficial and lame conversation falls on you. It is not the other person’s fault. That “other person” probably has not read this article or books on communication or even cares about improving their communication skills. Just by reading this article, I know that you are among a small percentage of people who want to do things better and make life more enjoyable. The majority of people go through life doing the same ol’ thing day after day after day without even considering that they can do something about that. It is up to you to captain this ship.

To guide your conversations into deeper waters, you must learn how to ask the right kind of questions. Deeper questions. Questions that require some thought and more than one or two words to answer. Let’s rework the conversation from above…

John: [Instead of John asking, “How was your week?”] “So, what was the most challenging thing about this week?
Sally: “I had a guy who was not happy with his order, and it took me an entire afternoon to fix it.”
John: “What happened to make him unhappy about his order?”
Sally: [Sally tells her story about what happened.]
John: “What did you do to help him?”
Sally: [Sally shares some more of her story.]
John: “How can you prevent that from happening to someone else?”
Sally: [Sally explains what she can do.]
John: “How great does that make you feel knowing that you spent the afternoon solving his problem? I bet he really appreciated that.”

What is different about this second conversation is the way that John asks Sally about her week. Instead of asking a question that requires very little thought and produces a stock response (“How was your week?”), Sally has to think about the most challenging part of her week; and John now has a dialogue with which he can continue to explore and ask more questions.

Two important things are happening as John continues to ask Sally followup questions based on what she is telling him about this challenge from her week.

  1. With each follow-up question, John is taking Sally from a place of superficial answers to a realm of emotion. By asking Sally for more details, Sally becomes emotionally involved in the conversation as she relives (in her mind) the experience. Of course, if Sally would have said that the most challenging thing about her week was that her dog, Skipper, died, then John could take a different approach and still create a deep conversation. For example… Perhaps John could respond with, “Oh, no! I am so sorry to hear that. How long did you have Skipper?”; and John could continue to ask questions as long as Sally wants to talk about it. The key for John is to guide Sally to all the happy times she had with Skipper. In other words, change Sally’s focus from Skipper’s death to great memories she had with Skipper. If you find yourself in a situation such as this… stay calm, be sensitive, and simply be there for the other person.
  2. John is making Sally feel like she is the most fascinating person in the world. This is my favorite method of building rapport and a connection with someone… Make the other person feel like they are the most fascinating person in the world. This is accomplished by eliminating all distractions and placing your entire focus on the person in front of you, and keep the conversation about the other person by asking questions that encourage them to open up.

I suggest you make a list of 20 questions that you feel comfortable asking others that are designed to elicit an answer that is more than one or two words and makes your conversation partner think. The questions you design should require a response that will allow you to ask more and deeper questions to keep the conversation going.

Here is a list of questions to get your mind started. These questions are designed to elicit an answer about which you can ask deeper questions…

Personal Setting

  • When you were young, what toy do you remember the most?
  • What did you think you were going to be when you grew up?
  • What is your all-time favorite city?
  • What is the most dangerous thing you have ever done?
  • Without telling me what you do, what is the most fulfilling aspect of what you do?

Business Setting

  • What do you ultimately want to be remembered for?
  • If you could go back and tell the younger you only one thing when starting your company, what do you think that would be?
  • What keeps you awake at night?
  • What makes you get out of bed every morning?
  • What one thing in your business could you change that would make the biggest positive impact?

Now, put your phone out of sight; and go practice asking better questions.


Bill Gladwell is an entertainer, speaker, and trainer as well as a self-contained, one-man spectacle and Social Dynamics expert.