How to Keep a Conversation Going – Without the Stress

I was fascinated when I heard this story about Richard Branson. Now I’ll share it with you:

Richard Branson is seen as an outgoing, adventurous, rebellious, highly successful entrepreneur. He embodies confidence and produces an aura that makes you think, “It doesn’t matter what he chooses to do, I bet he will be great at it.” He’s even been seen kiteboarding with a naked model on his back.

Branson must have some natural super-ability to connect with people, right?

WRONG. It wasn’t always that way, as Mary Mazzio points out with her insightful article in Time. She writes, “When Richard Branson was a young boy, he refused to talk to adults and would cling to the back of Eve’s skirt.” (Eve is Branson’s mom.) Rather than make excuses for Branson’s behavior, his mother decided to force him to learn how to speak to adults by dropping him off three miles away from home and telling him, “You will now walk home. You will have to talk to people to find your way home.” Oh, and Branson was around seven years old.

Guess what? It worked. “Richard started to become more comfortable interacting with adults,” writes Mazzio. Obviously it didn’t stop there. Branson took it WAY next level and became a famous icon of success and adventure.

And to think, he used to be shy and scared to talk to people.

Social Skills are Learned

Has this ever happened to you…

You’re in the middle of a conversation and you can just tell that it is quickly dying. After the other person finishes their thought it will be your turn to speak. Anxiety starts to build up because…

You have no idea what to say next.

It’s a terrible situation to be in. Trust me, I know because I’ve been there plenty of times. The effects can be devastating.

Maybe you really wanted to get to know the person, but you didn’t get the chance because the conversation died.

Maybe you just wanted to impress someone – it could be your boss, coworker, or even a stranger – but they totally lost interest once the conversation fizzled out.

Or maybe it’s not just one scenario, but a common theme. You want to meet new people and make more friends, but you’re unable to move the relationships further because your interactions don’t last long enough. People lose interest and choose to leave the conversations.

You may have asked yourself, is this what life’s like for someone who isn’t naturally social?

It doesn’t have to be. Just as we learned from Richard Branson’s childhood story, conversational skills can be learned just like most things in life.

Yes, I agree. That is exciting news.

And Branson’s not the only example. Countless people have struggled with the ability to keep a conversation going, only to flip the script and become confident socialites. I can tell you from personal experience that it was stressful just trying to figure out what to say next, let alone knowing how to make it interesting and captivating to the other people. But just as it happened for so many others, the tide has turned for me too. I now enjoy having conversations and love interacting with new people.

But first, I gotta warn you: there is one thing that you must have in order to succeed, and that is the true desire to improve yourself. Hopefully that’s why you’re reading this. If so, you have what it takes.

How Can Social Skills Change Your Life?

Take one minute and think about how your life would change if you really improved your ability to have good conversations with people. Seriously, stop reading for a minute and just think about the differences it could make.

…Minute’s up? Okay, so what kind of difference does it make?

• Are you happier, because your daily interactions are much more enjoyable?
• Do you have more, and better quality, friends – you know, the type that are there when you need help moving into your new place – because the people you meet enjoy talking to you and want to get to know you better?
• Have you removed stress from your life, because rather than becoming anxious during conversations or nervous just thinking about them, you are loving every minute of them?

Think those changes sound unrealistic? Think again. Not only are those improvements completely realistic, but the potential for an EVEN GREATER IMPACT is extremely possible as well. I’ll explain…

Social skills are arguably the most important skills a person needs to learn during their lifetime. They affect:

• Your ability to get the job you want, which accounts for roughly 40 hours of your life each week.
• Each and every relationship you have. That could be your boyfriend/girlfriend, coworkers, friends, family, husband/wife or anyone else you know.
• Your ability to create new relationships.
• So many other aspects of your life. From getting others to help you to negotiating a purchase, anytime you deal with others your social skills come into play.

They will even affect other areas that are less obvious. Let’s say you find out a group of coworkers are in a basketball league together and you love playing basketball. So you ask if you can join their team. Your ability to connect with them using your conversational skills can literally be the difference between them answering, “Sorry, our team is already full” and “Yea dude, that’d be great!”

It’s unfortunate, but the traditional school system has let us down. Social skills are so important to develop, yet they don’t do anything to teach us about them. Sure, school in and of itself is a social setting, but they don’t tell you that these are skills you can learn and improve upon, let alone give you any help with them. That is why I am here to fill in that void.

A Few Quick Notes

Over the years I have developed a repertoire of different strategies that help me keep conversations going with ease and very little stress. Very soon I will be sharing them with you.

But first I just want to preface these strategies by saying that conversations are extremely complex and dynamic. This can be a blessing because you have so many options with how to move a conversation forward, and many of those options can work great. There is not just one right answer. And even if you say something that doesn’t get a good reaction, you might be able to say something else right after it that gets you back on track. However, it can be a curse as well because you have so many options to choose from that you might not know what to say. You can get analysis paralysis, which means you are trying to analyze each option with too much thought and you end up thinking of a bunch of bad reactions you may get from each option, which then keeps you from saying any of them.

So the remedy to this would be to not over-analyze what you say or ask. When you think of something to say, say it. If it’s not the perfect answer, no big deal. If you accidentally offend them or ask a question that is too personal, they will tell you. Just genuinely say sorry and move forward.

Also, keep the context of the conversation in mind. If you’re in a social setting and you’ve started a conversation that the other person seems interested in, then it would be more fitting to try to get to know them. If you’re at the grocery store and started a conversation by asking which salsa to try, it doesn’t make sense to ask them what they do for work. However, if you are at the grocery store and see someone wearing a shirt from the volleyball league you used to play in, it’d be appropriate to mention it and see how they react. If it’s a positive reaction, you can try moving the conversation forward.

For the purpose of these strategies though, I am going to assume that you have started a conversation and are trying to find better ways to keep it going. You can check out my article on how to start a conversation with a stranger if you need any help there. You can also read my article on how to make a great first impression which will help you get your conversations started on the right foot.

Techniques, Tactics, and Strategies for Having Great Conversations

The techniques, tactics, and strategies provided below will boost your conversational skills instantly. The more you read this and understand the underlying principles, the faster and more noticeable your improvement will be.

And the best part is that these techniques are actionable. I will give you specific instructions on how to take the strategy and put it to use immediately.

But to get the most out of this, I recommend you read all the way through the post to fully grasp the different techniques. Then, choose one strategy and work on it until you are comfortable with it and can use it regularly in conversations. After that, choose another strategy to work on and do the same thing. Before long you will have zero trouble keeping a conversation going and you will trade in all that stress for excitement. Let’s start with one of my favorites:

1. The Plunging Stone Technique

When you throw a rock into the ocean, what happens? It hits the water and immediately goes straight down until it hits the deepest spot beneath it. And just as the stone’s goal is to move right through the shallow waters to get to that deep spot, the goal of the plunging stone technique is to move you from a shallow conversation and into a deep one – quickly.

There are two main benefits to this strategy. The first is that you will get the other person to open up and tell you things that they normally wouldn’t talk about in a “typical” conversation. This will help you connect with them better and faster because they will be sharing their feelings, and the reasons for those feelings, rather than just facts. This will make you stand out as someone who is a great conversationalist, even if they do more of the talking, just because you asked the right questions.

The second benefit is that you will get better quality information about the other person (and more of it), which will help you develop the conversation as it moves forward. You can relate to the info (“That reminds me of a time I was…”). You can dive deeper into a topic (“Oh, you’re a lawyer? One of my best friends is a lawyer too. He was telling me…”). Or maybe you are curious about something they brought up, so you ask them questions about it to try to learn more.

To use the Stone Plunging Technique, just use the following “FEW Steps” process:

1. Get a fact about the other person
2. Ask about an emotion related to the fact.
3. Figure out why they felt or feel that emotion.

The first letters of fact, emotion and why make up the F, E, and W in the “FEW Steps” process to help you remember it easily.

Sometimes you can get the “FEW Steps” answered in one question, and other times it will take a little more prodding. Here’s an example of John using this technique:

John: So what do you do for work? (This is where John is trying to get a fact about Chris.)

Chris: I’m a graphic designer.

John: Oh, cool. Do you enjoy your job? (Here he’s asking about and emotion related to the fact.)

Chris: Yea, man. I really enjoy it.

John: That’s awesome, dude. What is it about your job that makes you like it so much? (Now John is trying to figure out why Chris feels this way about his job.)

Chris: Well, I’m a freelancer, so I get to choose which clients I work with, which projects to take on, my workload, etc. That type of freedom is definitely a huge reason I love it so much. But I rent out my workspace from a design company that I’ve built a great relationship with. And I sometimes do work for them, if I choose. So I get the nice social aspect of working in a company, but the freedom of working on my own. Plus, I love the work I do. Creating and designing are what I would be doing in my free time anyway, so I’m killing two birds with one stone by doing it for a living too.

See what happened here? John was able to get Chris to really open up about something he loves. By getting Chris to tell him about his job, John learned so much about him. He didn’t just learn what he does for a living, he learned about his values, what he enjoys and how he was able to creatively make his job fit the lifestyle he wanted.

Most people stop after the first question. Some will ask the second question. But rarely do people dig enough to ask the third, which is the most important part. By taking that final step John was able to get some great information out of Chris, giving him a great opportunity to connect with Chris on a deeper level. I like to relate this to breaking down a beaver dam.

Let’s say you have a lake outside your house and the local beavers constantly build up a dam to raise the water level of the lake and create still, sitting water. (This actually happens and my Aunt and Uncle’s property.) When the water level starts to get too high, you have to go break the dam down again.

It may take around 20 strong jabs with your shovel to break the dam, but you don’t know exactly which hit is going to be the one to release the water flow. Well guess what? It’s similar with conversation and getting people to open up. Sometimes you can ask a person three questions and they won’t respond with much. But then you push it just a little further, ask that fourth question and BOOM, the floodgates open and they start sharing more than you could have imagined.

So remember, just like I said before – sometimes you will get a great answer from just one question and sometimes they still won’t give you much after the third question.

For example, you may ask someone what their favorite part of their trip to New York was, and they could answer with a full-blown story that really tells you why they enjoyed it.

However, it won’t always be that easy. Let’s say you just went through the first two steps – they are taking a music production class (fact), and they really enjoy it (emotion) – and you ask them why they like it so much. But instead of getting a great story or understanding, they just say they like the people in the class.

Rather than giving up or accepting that as the end of this topic, you can try to dig a little further. You could say something like, “Oh, interesting. I expected you to say you really liked the course material but you’re saying it’s the people that really make the class enjoyable?”. Or maybe something simple and to the point like, “What is it about the people in your class that you like so much?”. You never know, that just might be what is needed to really open the conversation.

You may be wondering, “So how do I know how much to prod? I don’t want to annoy and bother them.” And I completely agree. There a few things you want to think about.

Generally, if they respond with a short answer to your “why” question, it doesn’t mean they don’t want to give you a good answer. They may not think you care for more than that or just thought that was the answer you were seeking. So it should be fine to go a little deeper trying to figure out the “why” by asking the question in a different way that hopefully opens it up.

From there, you have to decide if you should continue with it or not. Pay attention to see if they seem irritated, uncomfortable or even just bored with the topic. In any of those cases, cut your loses and move onto a different topic. But it is entirely possible they just didn’t understand what you were looking for and all you need to do is rephrase the question. You will have to make a judgment call here.

One last thing to note before I give you some samples of facts, emotions, and whys and then your action plan. If you are trying to find the “why” to an emotion and it’s something that you obviously know the answer to (like asking Matt if it hurt when his girlfriend broke up with him when you know he was a train wreck), you don’t just want to ask why. Imagine asking, “Why did it hurt when she dumped you?”. Although you could just be curious, it sounds like you are saying you don’t get why he was hurt and are implying that he was just overreacting. To prevent this, it would be better to ask, “Sorry to hear about that. That’s really tough. What was the hardest part of the breakup for you?”.

You are still getting to the why, but rather than asking it in an insensitive way, you are letting Matt know that you understand his situation, you can empathize with him and that you are really curious to know more about the feelings behind this whole thing, maybe so you can learn from the situation.

Here are just a few samples of facts, emotions, and whys:

• Facts – where they work, their job position, who they know, what they read, what they listen to, sports they play/watch, their hobbies and interests, their values and beliefs. It can also be the opposite, like bands they don’t listen to, etc.
• Emotions – their likes, dislikes, fears, joys, worries, stresses, annoyances, curiosities, concerns. Also, things that anger, disgust, uplift, excite, fulfill, energize, arouse, or satisfy them.
• Whys – “What’s your favorite part of…”, “What is it about…that excites you so much?”, “Why don’t you like…”, “Why do you think…stresses you out so much?”

ACTION PLAN: The Plunging Stone Technique

1. Memorize the “FEW Steps” and use the word “FEW” to remind you – FACT, EMOTION, WHY?
   • Get a fact about the other person
   • Ask about an emotion related to the fact.
   • Figure out why they felt or feel that emotion.
2. Go through some plausible scenarios in your head. Pretend you are asking someone these questions and give yourself random answers. How might you respond to get the “why” out of them? Honestly, the more you do this, the better you will get and the easier it will be for you to start applying it to real conversations.
3. Start using it in conversations. A good way to ease into this technique is to use it in conversations you have with friends and family. If my sister went to Disneyland, rather than asking her, “How was it?” like most people would, I might ask, “What was your favorite part of the day?” or “What was the most memorable moment of the day?”

2. Ask Good, Interesting Questions

This technique focuses on getting other people to open up and divulge details about themselves, often in a fun and spontaneous way. Yes, I know your probably yelling at the screen saying, “Rob, the last technique was about asking good questions that make people open up. WTF?!? We can’t just ask them questions all day long!”

Well, you’re right! You definitely don’t want to ask a bunch of consecutive questions like an interview. But I am providing you with an easy-to-follow plan that will help you get much more out of the person you’re speaking to. And all this information will give you multiple conversational threads to work with as you develop the conversation (more on this later). Don’t worry, soon we will be going into the things that you should be talking about.

Now, back to asking good questions. There are a few attributes that your question must have in order to be great. It must:

• Not be a yes or no question (unless it contains a follow-up question that asks for them to go deeper). You want to word your question in such a way that their answer will require a story, a belief, some personal background or anything that just makes them open up to you.
• Be a question that they rarely hear, if ever.
• Make them think about their answer for a while. They shouldn’t have an answer ready since this isn’t a question they often get.
• Be fun! It can have some serious tones to it, but the point is to allow people to dream, relive good and happy memories, and think about alternate lives. When you can give someone the chance to step out of their shoes and visualize an amazing fantasy, they will think that you’re fascinating (and you haven’t even said much!).

I need to give you some caveats though:

1. You need to be in a conversation that the other person seems willing and able to stay in for at least another minute or so. If you’re in an elevator and their floor is arriving soon, it doesn’t make sense to go into this. But maybe both of you are in a long line and it’s a great way to kill the time. So if they look like they want to leave the conversation or you know they will have to leave shortly, take a pass.
2. It will work best if you have a reason for asking, so you should try to preface it by saying, “Earlier I heard this really interesting question and I’m curious how you’d respond.” Or some variation of that, like, “My friend told me this interesting question…” etc.
3. Be prepared with your own answer in case they don’t have much to say or ask you the same question right back. Sometimes people are caught off guard and have trouble coming up with an answer. That’s fine. Be understanding. You can offer your own response to the question to show that you aren’t just trying to dig into their brain and that this is a two-way street. And be sure that your answer paints you well! (More on this in storytelling later.)
4. Not everyone is going to buy in the way you are hoping. This is fine though. You can continue the conversation using other strategies. Sometimes they won’t get that the question is supposed to be fun and creative and sometimes they just aren’t in a creative mood or don’t have the energy. Just don’t take it personally and try to move forward using other means.

To help you understand this strategy better, I am going to give you some sample questions. Feel free to use any of these, or you can make up your own questions if you’d rather.

• “If you could be any famous person, who would you be and why?”
• “If you had an infinite supply of money, what would you spend your time doing and why?”
• “If you could only watch one movie for the rest of your life, what would it be and why?” (You can replace the “watch one movie” part with many other things like, “eat one food” or “do one activity”)
• And here’s one of my personal favorites – “If everyone you’ve ever known in your life disappeared from Earth and you had to start your life from scratch, where would you choose to start anew and why?”

Hopefully you get the idea. You’ll notice that the common theme in both of these first two techniques is to ask the person WHY this is their answer. That is where the conversational gold lives. By applying this strategy, you will notice a dramatic improvement in your ability to open people up and keep the conversation going.

Lastly, here’s another great question inspired by two different articles I read: Nat Eliason’s Second-Degree Dinners post and Steve Errey’s 5 Lines That Will Keep a Conversation Going. This question is a little more serious but can spark some amazing dialogue. So here it is (drum roll please):

“What’s Your Biggest Challenge?”

It can be about work or life in general, but it’s honestly one the of the best questions out there.

ACTION PLAN: Ask Good, Interesting Questions

1. Choose ONE good question to memorize. When you ask it, you want it to sound as natural as possible. Once you’ve asked this question several times, then you can start testing new questions.
2. Think about and memorize the way you would answer this question. You need to be prepared to answer it if they return the question or you need to open up to them before they want to answer.
3. Ask the question in your conversations. Remember to set up the question with a reason, like “My friend just asked me this interesting question. How would you respond?” Again, try using this on friends or family if want to gain confidence before using it on strangers.
4. BONUS: Take a mental note of their response and analyze it later. If it didn’t go over very well, no big deal. Just use it as an opportunity to learn something new and try to think of the possible reasons why.
   • Did you forget to preface it?
   • Did you have poor delivery?
   • Was it an inappropriate time to ask? Maybe you both were discussing an interesting topic and you just cut out of it to ask your question.
   • Were they already a little uncomfortable in the conversation?

3. Take Advantage of Conversational Threads by Listening Intently

A conversational thread is basically a topic of conversation. When someone says, “I like soccer because it keeps me active,” they have given you two conversational threads: soccer and being active.

To keep the conversation going you might pull on one of those conversational threads and run with it. Maybe you respond with, “Oh cool, me too. I play on a coed adult-league soccer team.” Or even, “Yeah, it’s similar for me too. I get bored with running and going to the gym, so I like to play racquetball with my friends.”

You are essentially using the information they provided to keep the conversation going. In the last example, you know that there’s a good chance of keeping or raising their interest by expanding on the topics of soccer or being active. Here’s another example:

For this reason, it is imperative that you become a good listener. Carl Rogers, an extremely influential American psychologist, words it perfectly:

“Man’s inability to communicate is a result of his failure to listen effectively.”

And it’s so true! By listening intently to the other person, you will better understand what they are communicating to you, which will help you relate to what they are saying. Not only that, but you will be much better at picking up on the different conversational threads, which is EXACTLY what you want to do.

The first two techniques in this article teach you how to make people open up, which will provide you with a plethora of useful information about them. By LISTENING to what they say, you can use that information to choose a conversational thread to continue.

When you hear a conversational thread that you think would be great for moving the conversation forward, try to act on it soon after it is mentioned. You don’t want to interrupt the person or end the current topic if it is a great discussion, but commenting on something they say right after they say it is much more relevant and makes more sense. For example, if someone mentions a psychology book they really enjoyed or that they had an amazing breakfast burrito this morning, I am going to jump all over it because those are two topics I want to get into more detail about. (Yup, I love breakfast burritos and am always looking to find better ones, but honestly who doesn’t?).

However, don’t stress out if you miss an opportunity to hop onto a conversational thread that just went by. You can pull on one thread, then let go and grab a different one, then come back and pull on the original thread. As you move through the conversation you will get more threads to pull on and you can always move back and forth between them.

Let’s say Christie mentions how much she loved Dan Pink’s book A Whole New Mind, but I wanted to keep talking to her about the current discussion of African geography (don’t I have fun conversations?!). Well, I can wait until we finish that thread and, once it winds down, bring up the book again. I can say something like, “Wait, you said you read and really liked A Whole New Mind right? I’ve read his other books but not that one. Should I put it at the top of my to-read list?”

A quick side note – some of you might be thinking, “Okay, I get what you’re doing but all you did was take that info and ask another question. I thought we weren’t going to hound people with questions.” That’s a good point. But I was just showing one example of how to get the thread going again. Let’s say Christie responded by telling me that it was a really good book. I could then tell her how I’m not surprised since his other books were good, go into what the other books were about, tell her why I liked them so much, and even go into my thoughts and philosophies regarding human psychology and why people do the things they do.

So the point of grabbing onto conversational threads is to open a dialogue that interests you both and that you both can talk about.

The beauty of this technique is that the number of conversational threads for you to work with will continue to grow as you move through the conversation. And often it won’t take long to get great information. It’s possible for 30 seconds of conversation to provide you with 30 minutes worth of topics to discuss.

This doesn’t mean that you’re forced to take an existing thread though. You can bring up a new topic of discussion in hopes of drawing the other person into that thread. But the point here is to teach you to find things to talk about by listening to the different topics the other person mentions.

I also need to point out that conversational threads can be facts, emotions, beliefs, etc. So don’t just pick up conversational threads about sports, health, and the weather. Try to relate to their emotions too.

For example, if someone tells you they just had an “Aha!” moment while designing something for work and it was such a great feeling, you can try to relate to their emotion of the “Aha!” moment. Maybe you had an “Aha!” moment a while back and you can tell them about that and go into a conversation about how great “Aha!” moments can be and how you think it’s important to try to get more of them into your life.

Lastly, when you are picking a thread out of an existing topic, you want it to be a smooth, natural and understandable transition. If someone mentions how they love roller coasters because the speed is such a thrill to them, don’t respond by saying, “I like racing cars.”

First, let them know you understand what they mean, then show how you can relate to that. So here would be a better response: “I know what you mean. That feeling of flying around is such a rush, I absolutely love it. That’s why I really enjoy racing cars.”

See the difference? In the first instance, you just cut off their thread about roller coasters and introduced yours about racing cars, which can seem rude. But in the second example, you related to what they were talking about (enjoying a thrill) and kept that thread going. The other person could then keep the “enjoying thrills” thread going by saying other things they do that give them a thrill, or maybe they would be interested in your car racing topic and move towards that thread.

ACTION PLAN: Take Advantage of Conversational Threads

1. Listen. Practice doing a better job of listening to people during all of your conversations. Consciously do this as often as possible.
2. Find the different conversational threads. By listening, you will hear the different possible conversational threads. Practice listening for them.
3. Pull on a conversational thread that you think will benefit the conversation. If it is something you both might be interested in, feel free to move into that direction. Make sure to properly transition into the new topic without interrupting the other person or abruptly shutting down a great discussion.

4. Turn One Piece of Information Into a Conversation

Above, I showed you how to find, take advantage and transition into different conversational threads. Now I am going to teach you how to take that one piece of information and turn it into a flowing conversation.

Once you’ve decided which topic you’d like to dive deeper into, you are either going to ask a question regarding that topic or you will relate to it in some way. By adding content to the topic, it increases the chances that the two of you will find something you’re both interested in discussing.

Asking About the Topic

Let’s say someone tells you that they like football, and what do you know, so do you! So you decide you’d like to go deeper into this topic. Well, one great way to do that is by asking them a question regarding football. Here are some examples:

• “Oh really? Me too. Who’s your favorite team?”
• “Oh cool. How’d you get so interested in football?”
• “Do you happen to know who won the Patriots game last night?”

By asking a question related to the topic, you are subtly telling them, “Hey, I was listening to you and realize we both have this in common. I think we’d both enjoy talking about it.” Except you aren’t actually saying those words. But it does show polished social skills.

Obviously, the questions will have to be tailored to the topic (you’re not going to ask who won the Patriots game if you want to talk to them about Sex and the City. But here are some things you may want to ask them about, regardless of the topic:

• Why or how they got so interested in the topic.
• What role it plays in their life.
• How it has impacted their life.
• What they know about it (something they can teach you, inform you about, help you understand, etc.)
• What they do/don’t like about it.

There are plenty of other questions you could ask, so when you hear someone mention a topic you’re interested in, ask whatever question piques your curiosity.

The difference between the Plunging Stone Technique and this one is that the former just gets any piece of information and tries to evoke an emotional response, whereas this technique focuses on choosing any topic that you want to discuss further and diving into it.

Relating to the Topic

You don’t have to ask a question. You can choose to relate to it and add to the discussion, which will hopefully catch the other person’s interest. Here are some possible ways to relate to it:

• With a story. Whether the story involves you or not, stories are a great way to add to the conversation (more on storytelling later).
• With facts. Teach them something that they might not know and show them that you do have knowledge on the topic.
• With curiosity. However, rather than showing your curiosity by asking them a question, you can state your curiosity. You can tell them that you’re interested in learning more about it because you’ve heard great things from other people, or what you hope to gain by putting more time into it, etc.
• With your feelings about it. Maybe it motivates you. Maybe it humbles you. However it makes you feel, you may choose to share these emotions AND the REASONS FOR these emotions.

Relating to the topic with your own comments can be extremely powerful. You get to show the other person who you are through your knowledge, emotions, curiosities, etc. Convey good qualities that the other person likes and you will be on your way to making a new friend.

ACTION PLAN: Turn One Piece of Information Into a Conversation

1. Think of (or write down) a topic that interests you. Imagine you are in a conversation and someone mentions one word related to that topic. Come up with three questions you could ask the other person regarding it and three different ways you could relate to it. Or feel free to come up with more. This will help you get a feel for how this works.
2. Repeat step 1 three more times but with different topics. Practicing this will strengthen the neural pathways for using this type of thought process, which will then make it easier to use in real conversation.
3. Use it in real conversation. When you hear someone mention something that interests you, ask about it or add to it. Just as in the other steps, feel free to start with people you are comfortable with before using it on strangers.

5. Storytelling

A great story can really help you build a connection with someone. Even if it’s not a story about you, it tells the other person a lot about how you think, what you find funny, etc. And if it is about you the story will relay facts about you, which can be much more effective than simply telling the other person directly.

Becoming a great storyteller can take a long time if you really want to perfect it. Just as a comedian tells the same stories over and over until they are perfected, you too will need to consciously comb through your stories and practice saying them to really make them good.

However, there are some tips you can follow which will help your stories instantly. One method to a great story comes from Andrew Stanton, the writer and director of Toy Story. Check out the great infographic from this post (based on Stanton’s rules) from the TED Blog by Kate Torgovnick May. It provides five important aspects to a good story. Here’s my quick synopsis on the five steps:

1. There need’s to be a problem or issue.
2. You take the audience on a journey with you.
3. There needs to be a reason or motivation for going on this journey.
4. The audience needs to relate to and like the protagonist.
5. The winning outcome.

This is great for serious stories. Maybe one of how you got to where you are today and how difficult some of the decisions were to make. But not all stories need to follow this standard format.

As long as the story has some element of surprise, takes the person along a journey and has some emotional swing in it, it can be good. For example, let’s say you were supposed to do a few quick errands one day but they ended up taking way longer than expected. By itself, it’s not that interesting. But if you add in the surprise, emotion and journey, it can be. Here’s a quick story I made out of it:

“That reminds me of our date night the other night. We just had a couple easy errands to run during the day – cash a check and ship a package – before the night got started. So we get to the bank and we’re second in line. No biggie. Then one person finishes and we’re next in line. It’s nice, the line’s moving fairly quickly. But then the one and only bank teller gets this weird look on her face and hurries into the back. Everyone is just confused. We were wondering if someone was robbing the bank or something. The line started building up and people were talking amongst each other in a very confused fashion. We were about to leave and finally she comes back after about 20 minutes. Anyway, we eventually get helped (which then took forever!) and leave the bank after almost an hour.

So we tell ourselves, well, UPS won’t take that long so we’ll be fine. WRONG. They couldn’t figure out the best way to ship our lamp and the staff kept arguing with each other. After almost an hour there of being antsy, we hurry home so we can start getting ready for the night. We got all dressed and ready, looked at the clock, then looked at each other. We could both see it in each other -the exhaustion and pent-up stress – we were over it. We were almost surely going to be late to the movie, so we said, “screw it.” A little disappointed, we ordered pizza, made popcorn and drank wine while watching a chick flick on the floor of our family room, bundled up in a bunch of blankets. It was supposed to be such an easy date night but, you know what, we had a blast anyway.”

This a simple, effective story. It wasn’t much had happened, but I brought the audience along on a journey (the errands, getting ready, then movie at home), with emotions (getting antsy because of the time, racing to get home and ready, the disappointment of missing date night, then the happiness of enjoying it as is), and surprises (supposed to be easy day but wasn’t, supposed to make it to date night but didn’t, supposed to be bummed but enjoyed it).

It’s good to be cognizant of the qualities you are portraying through your stories. It’s a very effective way to say good things about yourself without bragging. Telling a story that took place when you were in Panama is much better than directly telling the person that you went to Panama. Even in the story I just told, it might not seem like I made myself look better, but I did. I showed that I am spontaneous by being able to change date night on the fly. I also showed that I’m fairly positive and don’t dwell on negatives. Even though the official date night didn’t work out, I still had a great time rather than being bummed.

Some last tips: Stay positive. Even if you want to talk about something that didn’t go your way, make it a learning experience or laugh about how it’s funny that things can go SO against you. Or even something that just shows that you’re not letting it bother you and that you don’t dwell on the negatives.

Don’t worry if you screw it up or don’t deliver it well. Stories are rarely told perfectly in regular conversations, so it’s almost expected.

Also, start paying attention to the way other people are telling their stories. Think about what they did/didn’t do well and try to learn from it.

ACTION PLAN: Storytelling

1. Think of something interesting that has happened to you and think about how you could turn it into a good story. Go through this in your head or on paper and see what you can do to really mold the journey, emotion and surprising aspect of it.
2. When you are in conversations, listen for opportunities when you would be able to relate to something the other person said by telling them a story. Even if you don’t end up telling the story in that moment, it is good to get in the practice of listening for those opportunities.
3. And finally, start telling people stories. While talking to people, try to relate to some of the things they say with your own stories. Really make sure to tell them what you (or whoever the story is about) were feeling. It’s critical that the other person understand the emotions that are being felt throughout the story.

6. Remove Your Filter and Be Yourself

My buddy Dan Chang (founder of thefriendformula.com) has a great article on how to make you better at conversations by removing your filter. And it’s a very good point because many people are filtering too much of what they think, preventing a lot of words from coming out during conversation.

Trust me, you don’t want to be like this squirrel:

Your goal here is to say things in conversation when you think of them. Don’t think the thought, then try to decide whether you want to say it, then realize it’s too late to say it and never get the words out. You want to remove the filter that’s keeping you from engaging in conversation.

Now, there is a good reason why we have filters in the first place. We don’t want to offend people, say something that makes us look dumb, or get ourselves into trouble. However, the problem is that many of us have over-active filters that are filtering WAY TOO MUCH out of our conversations.

You want to say these things without worrying about how other people are going to perceive you. Not because you don’t care how they perceive you, but because it’s the worrying about how they perceive you that keeps you from being yourself and keeps you from having a nice flowing conversation – without the stress.

ACTION PLAN: Remove Your Filter and Be Yourself

We can thank Dan for these action steps:

1. Go to a place where you can speak out loud without anyone hearing you (car, bedroom, forest, wherever).
2. For 5 minutes, speak everything that comes to your mind. Yes, everything. It’s going to sound and feel weird – just do it. You will notice that you are probably filtering things even though you are by yourself!
3. Practice this once a day. At first it will be uncomfortable, but you will get more used to it the more you do it. This will teach your brain to be more comfortable speaking your mind in conversations.

Some Parting Words

Before you go, I want to say a few more things that will help your conversations that much more.

First, be passionate about the things you talk about. The energy and emotion you put into your conversations really sell what you are talking about. You don’t need to act like you’re on your 8th cup of coffee, just show that you are genuinely passionate (if you are). The same goes for your curiosity. When you ask questions, show that you are really interested and looking forward to hearing their thoughts.

Second, be positive. You will get much better feedback and interest if you are a positive person. Being a Debbie Downer is a sure way to losing them.

Lastly, support their hopes and dreams. I was just re-reading Charisma on Command (great book) by Charlie Houpert (charismaoncommand.com), which made me want to add this. If someone says a joke, a thought, a belief, an idea, whatever, embrace it and make them glad that they shared it. I’m not saying you have to agree with something that you don’t believe, but positive reinforcement works wonders in conversations. Just bring them up when you can and it will greatly benefit the convo.

That’s it. I hope you are able to put this to good use. These tactics have really helped me build strong relationships in my life, and I know they can for you too.

If you’re interested in learning how to make new friends and build better connections with people, you can also check out my free 8-lesson email course, Making New Friends The Easy Way .