Mastering the Art of Conversations: Free Preview

You’ve landed on a free preview of the Mastering the Art of Conversations course. We’ve selected two lessons that will help give you an idea of what this course is all about. You’ll find them below. If you’d like to access the rest of the lessons or course materials, you can purchase the course here:

Lesson 6 - Use Conversation Hooks to Start a Conversation with Anyone

“Who you are speaks so loudly I can’t hear what you’re saying.”

Conversation Openers

A lot of time is spent trying to figure out the perfect thing to say to open a conversation. You can find numerous books and classes on memorizing the perfect conversation openers. All the time spent memorizing conversation openers is a waste. When you use these canned openers, you will be perceived as inauthentic, and people can see right through that. To make things worse, you won’t know what to say after you’ve used the conversation opener.

There’s no magic trick for starting conversations

Each conversation is unique and there’s no rulebook on how to start them. You need to incorporate who the person is, where you both are, and what might be happening around you during your conversation in order for it to be successful. But if you don’t know anything about the person, where do you begin?

A flight jacket and a great conversation

One day at work, I came across a person wearing a brown jacket that looked similar to my grandpa’s World War II flight jacket. I decided to bring this up to the person who was wearing it. Ten minutes later, the conversation went from flight jackets to his family’s antique weapon collection, and finally, how he was part of a special task force that oversaw the overthrow of Saddam Hussein’s regime in 2003. Woah. What happened here?

Conversation Hooks

Like it or not, people perceive you based on your actions and what you wear. What you wear sends signals to people about how you’re feeling, what you care about, and how seriously you take yourself. Your actions indicate what’s important to you and what you’re trying to obtain.  A conversation hook can be any object or action that provides you with a slight tell about the person, which makes it easier to start a conversation. 

Examples of conversation hooks:

  • Clothing with your favorite band, movie, or sports team on it. 
  • Your cellphone with a decorative Star Wars case.
  • The book or magazine you took to the coffee shop. 
  • Tattoos, friendly ones that is, best not to ask about the Tattoo related to a crime.

Conversation hooks serve as an indicator to others what you’re interested in, so it makes it much easier to start a conversation. By showing your interests to others, you make yourself more approachable and easier to talk to. The conversation hook provides the much-needed commonality that makes the conversation easier to take place.

Using A Conversation Hook

Now that you have spotted someone with a conversation hook, it’s time to start a conversation. Take the conversation hook and use it as the initial opener to the person. “Hey, I see you like Star Wars, what did you think about The Last Jedi?” “You’re reading Lord of The Rings, what did you think about the battle of Helm’s Deep?” These are all simple examples, but there’s no right way of doing it. The only wrong way of doing it is not acting upon the conversation hooks you see.

Conversation Hooks are Tribal

Not only do conversation hooks represent what you like, but also they indicate what tribe you belong to. Like it or not, we are a very tribal species. We look favorably upon those who are part of our tribe and are more willing to cooperate with tribemates than non-tribe members. If someone indicates they are part of your tribe, it means:

  1. You are inclined to like the person because they are similar to you. 
  2. You have a common interest you can talk about. 
  3. You now have a channel of communication to get the conversation going.

To Do:

  1. Open your conversation journal to practice the exercises for this lesson.
  2. The next time you see someone, see how many conversations hooks you can spot.
  3. What do the conversation hooks tell you about the person?
  4. Try to use the conversation hooks to start a conversation.

Lesson 8 - How to Deepen Relationships for Richer Conversations

“In the end, there doesn’t have to be anyone who understands you. There just has to be someone who wants to.”

The Depth of Your Relationship Defines Your Conversation

Your relationships have a range of conversational norms that are deemed appropriate for the relationship. The level of depth of your relationships can range from unfamiliar, familiar, intimate, and meaningful. The levels are stacked upon each other like a pyramid with unfamiliar on the bottom, familiar on the second level, intimate on third level, and meaningful on the top.

In order to get to the top of the pyramid, you have to give each supporting layer time to harden so it can support the weight of the next level. Each person you know requires a time investment if you wish to increase the depth of the relationship. 

Four Levels of the Relationship Depth Pyramid

Level number 1 – Unfamiliar (Trust level: non-existent):  A stranger, possibly someone you’ve read about, seen around the office, or heard friends mention. Focuses mainly on facts and small talk about work, sports, and what’s on Netflix. Most of your regular conversations with strangers, acquaintances, or colleagues will fall into this category.

  • Examples of Conversation Starter:
    • How are you doing? 
    • How goes your work? 
    • Doing anything fun this weekend? 
    • Have you read or watched anything good recently?

Level number 2 – Familiar (Trust level: low): An acquaintance you’ve spoken with a few times. Conversations have likely stuck to small-talk. Focuses on feelings, goals, and non-polarizing beliefs. Here we can seek out advice for things you’re trying to get done. Talk about hobbies and side projects. Usually, you have these conversations with your friends. 

  • Examples of Conversation Starter: 
    • How are things going with that project you were working on?
    • I heard you were completing your pilot’s license, how is that going?
    • Did you hear Frank landed the promotion? 

Level number 3 –  Intimate (Trust level: medium): You have met this person multiple times, or have worked with them. You share information with each other and are willing to help each other out. Your trust in them has limits, but you feel comfortable being candid about some things.

  •  Examples of Conversation Starters: 
    • Last time we spoke you told me you were having an issue with Mark. Was that resolved? Anything I can do to help?
    • I’m thinking about (buying or doing something), do you have any advice?

Lever number 4 – Meaningful (Trust level: high): We talk about our vision for the future, our core beliefs, and our vulnerabilities. You have built enough trust to  provide the person with feedback regarding issues they are running into and you are receptive towards their feedback. You can talk about small challenges in life such as looking for a new job, trouble at work, relationship issues, etc. At this level, you learn about what drives that person and what they are trying to achieve. Usually, you have these conversations with your close friends.

  •  Examples of Conversation Starters: 
    • I noticed you really have your life together when it pertains to (goals, family, relationships), and I’m sort of struggling. What do you think I can do to improve?
    • Based on what you have said to me, I’ve noticed you have been struggling at work, anything I can do to help? I have a few things that helped me when I struggle at work. Would you be ok if I shared them with you?
    • What do you think about Frank? I’m having an issue with him and I need your advice on how to resolve this.
    • I’m thinking about making a big career move, and I want to know if you had any feedback for me?

Moving Up The Pyramid

In order to increase the odds of you reaching the top of the pyramid, it requires developing trust which is created through familiarity, honesty, and integrity

Familiarity: How often do you contact this person? Does this person see you on a regular basis? By taking time out of your day to regularly meet with this person, you’re demonstrating to them you find value in the relationship.

Honesty: Have you been open to this person? You need to be a little vulnerable to this person and share bits about yourself to show the person you are willing to open yourself up to them. If they see that you’re genuine, odds are they will open themselves up to you too.

Integrity: Has this person asked you to do something? If so, you need to make sure you follow through. Has the person asked you to hold a secret? You will need to hold onto this secret to prove your loyalty to this person.

It takes time to develop that and if you rush to climb the pyramid you will fall off. If you want a real example of this, think of the time you met with someone and within the first 10 minutes, they shared all of their innermost secrets. Ya, creepy.

Testing the Waters

What if you don’t know if you can reach a higher level of the pyramid, but you want to at least see if it’s possible? You would phrase your questions without a leading statement. So instead of saying, “You know what I really think this company needs to change its strategy.” Instead, you would phrase it as a question, “What do you think about our companies strategy?” So it gives the other person room to either start talking about the subject or not. Either way, it allows the other person an opening to express their feelings when they are ready, instead of you exposing yourself and risking hurting the relationship. If the person opens up, good; you might be able to move to a higher level. If the person becomes defensive, back off; and keep the relationship at the current level.

To Do:

  1. Open your conversation journal to practice the exercises for this lesson.
  2. Assess your current relationships to see where they land on the pyramid.
  3. Of the lower level relationships, have you tried seeing what you can do to move them up a level?
  4. Try to move a level 1 relationship to level 2. If you get pushback, relent. If it works, proceed to deepen the relationship.


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Meet Your Instructor

Jordan Thibodeau

Jordan has spent over a decade forging relationships with CEOs, authors, and entrepreneurs through his professional work on Google’s Mergers and Acquisitions Team, and Google’s Talks Program - a TED-like series recorded for offices worldwide. Jordan’s also the community manager and founder of the Silicon Valley Investor’s Club (SVIC).

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