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Getting to Know You – How deep can you go?

how-deep-to-discuss2I have a friend who’s always said you don’t have to get to know someone in the first 5 minutes… or even the first few times you meet. It takes a lifetime to get to know someone. How true that is. And yet, for many, our tendency is to rush and learn as quickly as possible if someone we meet will remain an acquaintance or become a true friend.

While people seem to be increasingly good at texting, snap-chatting, tweeting and facebook posting, conversation is becoming a lost art. Perhaps this is part of the reason why icebreaker questions and conversation prompts have proliferated online. Another explanation could be the fact that our lives are increasingly complex and the number of people we “connect” with has grown exponentially. In response, our tendency is to find communication shortcuts and determine as quickly as possible if we want to invest our precious time into getting to know someone better.  Whatever the reason, we hunger for new questions to prompt conversations–prompts that are a step up from “do you come here often?”

4 levels of discussion prompts

In recent years, I’ve scanned through hundreds of conversation prompts that folks have posted online. Some I’ve found to be pretty good; but others, to be honest, are rather uninspiring. Admittedly, determining the right question to ask to start a conversation, is hard.  The “best questions” to ask may depend on your goals, how well you already know the other person, the type of relationship you want to develop, and how intimately you want to connect with them. In other words, how deep do you want to get?

When evaluating and considering discussion prompts, think of these four levels as a continuum from easy-to-answer surface questions to deeper and more introspective let’s-get-personal questions:

  • LEVEL 1: Icebreaker questions – surface questions to stimulate casual conversation
  • LEVEL 2: Common ground questions – find shared interests and build new relationships
  • LEVEL 3: Getting to know you questions – probing prompts to get to the real you
  • LEVEL 4: Deep-Dive questions – deeper discussions to build intimacy and understanding or to address specific challenges

Through this lens, those discussion prompts that I initially found to be uninspiring are better understood as Level 1 “Icebreaker questions.”  If you just want to scratch the surface or make light conversation, then there’s nothing wrong with a question like, “What’s your favorite fast food restaurant?” or “What’s your favorite cartoon character?”  Such questions are not necessarily conversation starters or relationship-builders, but they can help you break the silence and get people talking to, and maybe laughing with, each other.

For those who want to go a little deeper than simply talking about the weather or other superficial topics, Level 2 discussion prompts help people find common ground — that is, topics and interests they might share. These prompts should be easy to answer and not delve too deeply into inner secrets. The goal is to use these questions to determine with whom you might like to build deeper relationships.

Moving down to Level 3, Getting to know you questions start to uncover the real person. While these may take a little more thought to answer, they are likely to reveal more about an individual’s goals, ambitions, and past experiences. Prompts that fall into these categories include: A high school regret, How your birth order affected you, Something I’d like to learn, A major decision, A memorable moment, etc.

Level 4 Deep-Dive questions can grow more intimate or delve into a specific topic like stress, diversity, or team dynamics. In Mandy Len Catron’s New York Times essay, “To Fall in Love With Anyone, Do This,” she references a study by psychologist Arthur Aron who “succeeded in making two strangers fall in love in his laboratory.” The study went like this: “A heterosexual man and woman enter the lab through separate doors. They sit face to face and answer a series of 36 increasingly personal questions. Then they stare silently into each other’s eyes for four minutes.” 6 months later, the couple married! In his study, Aron categorized his questions into three levels. He skips over the more trivial icebreaker questions, starting with this one: “Given the choice of anyone in the world, who would you want as a dinner guest?”; and ending with, “Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.”

The two core principles in his study are:  1) as you grow more comfortable, you become more willing to answer personal questions; 2) the experience of discussing personal topics truly does bring people closer together.

“A lifetime” vs. “the right questions”

While not everyone looking for conversation prompts is hoping to fall in love, many long for a way to connect more deeply with the people in their lives–at work, at home, and in the community.  Depending on your goals, and how deep you want to go, you can find loads of discussion questions online, as I mentioned earlier.  Unfortunately, they’re generally not sorted by goals or levels of conversational intimacy.

An easy and playful resource for discussion topics that are categorized by level are the Trainers Warehouse line of Thumballs (created by Answers in Motion). Each ball is imprinted with 32 specially selected prompts for a specific depth of communication — breaking the ice, finding common ground, getting to know each other  and diving deep. If the sequence of questions is not important (as it is in the 36 Questions), the spirit of play brought in by the Thumball can also help to reduce stress and foster increased sharing.  You might choose to have each participant answer a different question, or have everyone respond to the same prompt before jumping to the next one.  Thumball activities are also incredibly easy to facilitate. All you need to do is select the one best suited to your group’s needs.

Although it might take a lifetime to truly know someone, a handful of really good discussion prompts can get you pretty close, in a much shorter time.

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