The Ultimate Guide To Social Skills
By reading this Ultimate Guide you’re already taking the first steps on your journey to a Rich Life. This is only an introduction to the ideas and material you’ll find inside IWT.
I started this site in 2004 while I was studying technology and psychology at Stanford. I’ve spent the time since testing and honing my Rich Life systems on thousands of successful students.
At IWT you’ll learn –
Buy all the lattes you want. A $5 coffee is not going to change your financial life. But learning how to automatically invest, how to select the right asset allocation, and how to negotiate a $15,000 raise will. I believe in asking $30,000 questions, not $3 questions.
Your Rich Life is yours. A Rich Life can be picking up your kids everyday from school. Or buying a $1,000 cashmere sweater. It can be buying a round of drinks for your friends, or traveling for 8 weeks per year. You decide. Your Rich Life is yours.
There’s a limit to how much you can cut, but no limit to how much you can earn. I have readers who earn $50,000/year and ones who earn $750,000/year. We’ve helped tens of thousands of people earn more money by negotiating their salaries, investing, and starting businesses.
Spend extravagantly on the things you love, as long as you cut costs mercilessly on the things you don’t. I don’t believe in cutting back on lattes. In fact, I want you to spend more on the things you love. What if you could double your spending on travel, or eating out, convenience, or charity? I call those Money Dials and I’ll show you how.
The 85% Solution: Getting started is more important than becoming an expert. You don’t need to be perfect to take control of your money. It’s OK to make mistakes. Get 85% of the way there and move on with your life.
Investing should be very boring—and very profitable—over the long term. I get more excited eating tacos than checking my investment returns.
You’re in control. This isn’t a Disney movie and nobody’s coming to rescue you. Fortunately, you can take control of your finances and build your Rich Life.
Money is political. You can simultaneously acknowledge personal responsibility and real systemic problems. This is a core part of the I Will Teach You To Be Rich philosophy. Housing is political. Healthcare is political. Voting rights are political. If you’re looking for bland tips on cutting coupons, this site is not for you.
I consider it a tragedy to live a smaller life than you have to. So many of us have been raised to believe that money is something to be scared of. We use phrases like “I’m not good with money” or “Money changes people.” Yes, money does change people. Money allowed me to dream bigger, to be more generous, and to be more adventurous. It can do the same for you.
A Rich Life is lived outside the spreadsheet. What’s the point of all this saving and investing if you’re simply going to wait until you’re 80 to live? No thanks. I believe that once you’ve set up your finances, you’ll see that the most important part of a Rich Life is outside the spreadsheet—it involves relationships, new experiences, and giving back. You earned it.
Welcome to your Rich Life journey, I’m excited to see what you do next.
What if you could talk to anyone, anytime, anywhere and never worry about awkward silences or saying the wrong things? Wouldn’t that feel great?
When you first meet someone, what do they notice about you? Beyond how you look.
They don’t see your education.
They don’t see how hard you’ve worked.
They can’t tell how funny and nice you are behind closed doors.
All they know is how you make them feel in the first few seconds of meeting them. And if you don’t make them feel good, they’re probably already thinking about how to gracefully and quickly move on. Tough, but true.
If your social skills aren’t where you want them to be, it can be tough to live a truly Rich Life.
That’s why in this Ultimate Guide, I’m going to show you how to quickly and easily improve your social skills. You’ll learn how to use the power of body language and charisma to create lasting connections with people.
The next time you’re out at a bar, a wedding, or an event, you’ll be able to confidently approach new people and always know exactly what to say.
No more being forgettable. No more feeling like a wallflower. And definitely no more awkwardness.
I’ve spent years studying, testing, and refining the best strategies for improving these skills — and I’m going to walk you through how you can improve your social skills in this guide.
For this guide, I’ve also brought in a few of my expert friends. Here’s a snapshot of some of the social skills experts you’ll meet:
Olivia Fox-Cabane: Author of The Charisma Myth
Michael Ellsberg: Author and Public Speaker
Ron Lieber: Award-winning journalist for The New York Times
Why I wrote this guide
I used to be socially awkward.
I would say all the wrong things at exactly the wrong times. Everyone would just stare at me in silence, and I’d burn with embarrassment.
I avoided working on this problem for years because, after all, I was doing just fine. Other than the occasional uncomfortable moment, what was the rush to improve? What were the real consequences of not being socially skilled?
But I realized that’s exactly the point: Things were just FINE.
Just like you can get fat by eating poorly for decades, you can actually do just FINE going through life without connecting with the people around you.
But every day you settle for just FINE, you’re losing out.
Maybe you say the wrong things (and don’t even know it). What do people think about you after you’ve left?
Do you miss out on opportunities and invitations because you come across as awkward?
Or maybe when you talk to someone at a bar, or a coffee shop, or a friend’s house party, you’re forgotten about minutes later?
It doesn’t have to be that way.
Over time, I’ve learned how to improve my social skills and shown thousands of my students how to do the same.
Today, I’m much more confident and charismatic. And even though I’m nowhere near perfect, I’ve given speeches in front of thousands of people and been on national TV. Yes, I said national TV.
And now, I even have my own Netflix show. If you haven’t seen it yet, you can check it out here.
For a guy that used to fumble his way through saying “Hi” to someone new, that’s a huge change.
You can make these same changes. And I want to teach you how because your ability to connect with the people around you is the single greatest competitive advantage you can get.
A Rich Life isn’t just about improving what’s on the inside — it’s just as important to control what people think when they meet you.
In this guide you’ll learn:
Why Social Skills Are More Important Than People Think
Many of us don’t realize the cost of having poor social skills or the power we’d gain if we improved them. In Part 2, I’ll show you why improving your social skills is something you can’t afford to ignore.
How To Make Small Talk
Want to meet new people and be able to start interesting conversations? In Part 3, I reveal the common mistakes most people make and show you some simple ways to make small talk with anyone.
Overcoming Shyness & Building Confidence
Can you learn to overcome shyness and become more confident? Most people assume the answer is no. But confidence is a skill, and like any other skill, you can master it over time.
How To Master Group Conversations – Simply And Effectively
I know firsthand that being that awkward guy (or girl) in social and professional situations is the worst. It’s embarrassing and unpleasant for everyone. Learn my best strategies for overcoming anxiety and being confident in group settings.
How To Be More Likeable
Everyone has that friend who can walk into a bar and talk to anybody with ease. How do they do it? Learn the secrets for getting people to like you, instantly.
Take Your Social Skills to a New Level
It’s time to put your new social skills into action. You’ve learned how to be more confident and taken your social skills to a whole other level. So what’s next?
Part 2 – Why Social Skills Are More Important Than People Think
Have you ever totally embarrassed yourself in front of someone you just met?
Maybe you’ve done something like offered a drink to a recovering alcoholic at a bar? (Yes, I actually did this.) Or told a joke that completely bombed? Or maybe you’ve tried to start up a conversation…only to have it die out a few moments later?
If any of these sound familiar to you, then you know the importance of social skills.
But these examples only scratch the surface.
The true cost of not having this skill goes much deeper than just feeling uncomfortable or embarrassed from time to time.
Here are three key reasons why social skills are so important to your life.
Reason #1 – Poor social skills have hidden costs
You might think social skills only matter for dating and parties, but they’re absolutely crucial in business, too. They can be the difference between getting a massive payday or nothing at all.
Here’s an example: One of my friends runs a successful tech business and was considering acquiring a small, 1-man company.
After a night of drinking, he asked me what I thought of the guy behind the 1-man company. As a friend, I told him the brutal truth: The guy was way too cocky for his experience, I wouldn’t want him on my team, and I told him exactly why.
My friend canceled the acquisition the next day. That guy will never know that his social skills cost him a 7-figure payday.
While it might not be a million-dollar payday that you miss, that same thing is happening in your workplace every day.
Your boss looks at his boss and, at review time, they both agree some people just aren’t management material. Or they’re not ready for the best projects.
If you can’t deal with people the right way, opportunities will keep passing you by. Are they passing you by?
Reason #2 – Even the “naturals” work hard to be liked
Take a second to imagine your favorite celebrity being interviewed on a talk show.
If you want to see someone who applies rigorous testing and practice before taking their work to a public stage, look at Chris Rock. It takes him at least 6 months just to develop an HOUR-long stand up show. But by the time Rock arrives on stage, he’s flawless.
You can take this same approach with your social skills.
Yes, improving what you say and how you interact with others will take some practice. And yes, it can feel a little weird to work on this. But every highly socially skilled person works on this — even if they’re just practicing in ordinary conversations day-to-day.
Reason #3 – If your social skills are missing the mark, nobody will tell you
Imagine you’re about to go on a date or job interview. You don’t know it, but there’s a piece of spinach stuck in your teeth, and even though everyone sees it, nobody tells you about it!
A lot of us go through life like this. We have little idiosyncrasies that turn people off or keep us from making a good impression. Most of us never learn what they are, but once we’re aware of them, our lives can change dramatically.
Here’s an example: Back in high school I applied to dozens of scholarships.
Even though I was a great candidate on paper, I could never get past the interviews. I never understood why until I videotaped myself giving a mock interview. When I watched the tape, I realized I never smiled!
I thought I was coming across as a fun, gregarious guy, but watching that tape I looked like a dull, humorless robot.
That was a crucial piece of feedback that I was missing — and no one in the interviews told me about it. Instead, opportunities just kept passing right by me, and I didn’t know why.
Of course, there are other ways to get feedback besides taping yourself, but the rewards can be just as profound.
Take a look at my friend, Michael Ellsberg, as an example. He’s someone who went from being a total loser in high school to becoming a successful writer, speaker, and author of “The Education of Millionaires.”
And one of the biggest turning points in his life came from getting brutal and honest feedback. The experience was so powerful, he broke down in tears right there on the spot.
In this interview, which you cannot find anywhere else, you’ll learn:
- The very painful — but necessary — starting point for any kind of personal growth work.
- How to get candid, brutally honest feedback from people instead of whitewashed compliments
- The mental strategy for handling criticism from people very close to you (like your parents)
Part 3 – How To Make Small Talk
Do you know someone who can strike up a conversation with everybody they meet? Their conversations look effortless, they often get free drinks at the bar, and they make best friends any time they go out.
How do these people do it? Are they some type of social mutants? Or are they just “naturals” when it comes to talking to people?
They may be gifted, but they don’t have some coveted secret. Instead, they’ve just mastered the art of small talk: That oh-so-elusive skill that many people claim to hate.
But listen, small talk doesn’t have to be icky or boring “How’s the weather?” chats. You can actually use small talk to dive into much deeper conversations. It can be the basis for great relationships and making new friends.
How to be interesting
The key to small talk is being interesting. If you’re not interesting, you can actually see people’s eyes glaze over.
Whenever I used to talk at a party or in work meetings, people would give me blank stares and completely check out. For a long time I had no idea what was going on, but I eventually discovered the mistake I was making.
Check out this short video clip, where I break down exactly what I was doing wrong.
Live small talk teardowns and word-for-word scripts for you to try out
Alright, now that we’ve laid the foundation, let’s dive into the details.
In the video, I explain how small talk really works, give you some simple tips to master it, and even include a LIVE teardown of someone making small talk. You can apply the insights from this conversation to the next one you have and make yours a success.
Check out these small talk hacks:
- How do you make small talk (1:00)
- How to take the active role in the conversation to help it flow in the direction you want it to (1:47)
- How to keep the conversation exciting with an actual teardown interview with one of our IWT students (2:32)
How do you keep the conversation going smoothly?
We’ve all been in conversations that suddenly fizzle out. One minute, you’re standing there chatting away. The next, you’re awkwardly looking around and frantically searching for something clever to say…but the words just won’t come.
Does this happen to you?
It doesn’t have to. With a few easy tricks, you can keep any conversation rolling along at just the right pace — without asking too many questions or talking too much.
Let me show you how in this 2-minute video:
How to skillfully exit a boring conversation
As fun as it is to talk to new people, eventually every conversation must come to an end.
But for a lot of people, it can be hard to escape. Especially if you’ve followed the tips from above, you’ll have people that never want you to go away.
Rather than just awkwardly backing away from them or making lame excuses that you have to go, here’s how you can skillfully end any conversation — and still keep good rapport with the person you’re speaking to.
It’s a simple tip, but it’s ultra handy, especially if you ever find yourself in the midst of a weird conversation and want out.
Watch it here:
The two things in any conversation that make you want to leave (0:30)
What to do when the conversation is coming to a natural close (1:01)
What happens when someone is monopolizing your time and won’t let you go (1:53)
Part 4 – Overcoming Shyness & Building Confidence
We all feel awkward and unsure at times.
Just think back to your first day of high school or at your job. Did you feel vulnerable? Were you unsure of what to say or how to connect with other people?
While that’s a common feeling, what if you could go into new situations without feeling that way ever again? Imagine if you always felt confident and natural when you tried new things or met new people.
You actually can! Like any other skill, confidence is something that can be improved — and even mastered — over time.
Confidence Technique #1 – The Invisibility Cloak Technique
Here is a simple but effective way to cover up your fears and anxieties when entering an uncomfortable situation.
It goes like this: Whenever you’re in a social situation, imagine you’re wearing a cloak that makes you invisible or covers up certain parts of you.
Now, it’d be weird if you walked around with a crazy Halloween mask or cape on and went into a Starbucks saying, “Greetings, how’s your day?”
Not going to go well.
But what if, mentally, you can apply this same tactic? If I go to a conference, I’ll put on my Invisibility Cloak which allows me to feel confident and say, “Who am I going to be today? What is my behavior going to reflect?”
If I want to be a gregarious, friendly, outgoing guy, I’m not changing who I am on the inside to be inauthentic. I’m just changing my behavior on the outside.
What you’ll find is that over time, your attitude will change to match your behavior.
Confidence Technique #2 – Make confidence building a game
Here are two fun ways you can build up your confidence: The 60 Seconds Game and the Compliments Game
How to eliminate shyness for good
Many shy people can use the tactics above to boost their confidence for a little while but find themselves slipping back into their timid habits.
Luckily, overcoming shyness is easier than you’d expect. In fact, it just takes a subtle mental shift to rid yourself of this pesky emotion for good.
In the video below, I’ll show you a simple technique you can use to stop feeling shy today.
- Watch as I shed some light on shyness, and why shy people think and behave the way they do (1:03)
- One way to change the way you think about shyness (1:29)
- One technique to help you become less shy and more confident in your social interactions (2:45)
Remember: Confidence is a skill
Part 5 – How To Master Group Conversations – Simply And Effectively
Group conversations can be very tricky.
Groups come with a lot of moving parts. No one can predict exactly what someone else will say, who will show up, or where you’ll even be. While that’s part of the fun of being in a group, it can be stressful if you’re not sure how to behave or what to say in group settings.
In these situations, it’s normal to feel excluded and anxious. It’s normal to wonder, “What do these people think about me?” All of these things are normal.
But with the right tools and a little bit of practice, you can be as confident talking with a group of strangers as you are with your close friends.
How to feel at ease in groups
The number one thing you can do to make great impressions in group settings is get proactive.
Think about it. How many people just show up to a group event and stand there with their backs against the wall, expecting to be entertained by someone else?
That’s not only rude, it’s a terrible strategy for making a good impression. When you do this, you’re leaving what everyone thinks of you up to chance.
The better approach is to take control of the situation — so you decide how people remember you.
You can accomplish this in a couple of different ways:
1. Brainstorm a list of topics to talk about BEFORE you ever get to the event.
That way you don’t have to stand there awkwardly, trying to come up with clever things to say.
What should be on your list?
People want to talk about what other people are talking about. To get a shortlist, just look at the news, Twitter, or Facebook. The trending topics 26 on these platforms are the perfect kinds of things to bring up in group conversations. Plus, they make for easy icebreakers and allow you to be proactive in striking up conversations.
So you might say something like, “Did you see what so-and-so did at the MTV Video Music Awards OR the VMAs yesterday?” Or, “Woah, did you know what so-and-so is doing?”
It encourages people in the group to chime in and say, “Yeah! I saw that! That was crazy!” Or you’ll have others who say, “No, what’s happening?” Then you can explain it briefly to kickstart a deeper conversation.
It’s a great way to get a group conversation rolling along and everyone engaged.
2. Plan the type of impression you want to leave on people.
To do that, ask yourself:
When you spend some time planning these things out, you can have some conversation ideas on hand that give off the impression you want.
For example, if you want to make people laugh, prepare a few jokes and a list of funny things to talk about. If you want people to know you’re intelligent, do a little research and put together a list of fun facts to drop into a discussion.
The point is by doing this up front, you remove all the guesswork. You’re prepared with material to use when the opportunity is right.
3. Engage everyone in the conversation
The next step to making a great impression in group events is to engage everyone.
One thing that irritates me at group events is when you see two people having a conversation all by themselves. Sometimes they’ll even talk loud enough that no one else can speak.
Don’t be those people. If you’re speaking, engage other people as much as you can.
You can do it by using my humbly titled S.E.T.H.I. technique.
Simple, but very effective. In a group, you naturally trust, like, and gravitate toward people with genuine smiles. In the beginning, forcing yourself to smile more might feel fake, but keep practicing. It’s worth it.
Take whatever energy level you’re at now and add 50% more energy. Test it in small, anonymous places like at a coffee shop. See what kind of reactions you get. Then work up to using it at work and with your friends. You’ll be amazed at the difference.
Fast talking is a sure-fire way to make people tune out. If you’re a fasttalker, forcing yourself to slow down, while awkward for you, will be a welcome change to your listeners.
Your hands can be very expressive. Adding gestures (and not hiding your hands in your pockets or crossing your arms) can dramatically improve your communication.
The most socially fluent people don’t avoid eye contact, nor do they stare down other people. They look at you, they look away, then they come back. You can practice this rhythm, too.
How to instantly and deeply connect with more people
All these tactics help you once you’ve gotten a conversation to spark. But sometimes you’ll need an extra push — a way of deeply connecting with people even if it feels a little weird at first.
That’s why I want to share one of my favorite interviews with you. It’s from a session I had with one of my good friends Ron Lieber.
Ron Lieber is an award-winning journalist who writes the “Your Money” column for The New York Times. Watch as he discusses his techniques for creating instant rapport with someone he meets for the first time.
Here’s just some of what we covered in our conversation:
- How to strike up a conversation with anyone — and go deeper than the generic, “Hi, how are you?”
- The fun “conversational game” you can play to rapidly build your personal-connection skills
Part 6 – How To Be More Likeable
If you were to ask someone, they’d probably say, “Smile more!” That’s good advice, but there is another simple technique just as powerful (if not more) — eye contact.
It seems so obvious, but most people overlook it. They don’t consciously use eye contact, which is a shame because it is one of the most valuable tools you have at your disposal. With a half-second look, you can convey anything from confidence to insecurity to friendliness.
Eye contact is a key piece of my S.E.T.H.I. technique, but I want to give you a special eye contact challenge you can use to quickly improve how you use eye contact.
The Eye Contact Challenge
Yes, I’m asking you to test your eye contact. Notice I’m not saying, “Get better at it!” I want you to see the difference when you try different types of eye contact. When done correctly, it can build rapport and intimacy. When done poorly, it can make you look like a serial killer.
Here’s how to do it: Try holding eye contact for a second longer than you normally would. Practice on your waiter, barista, or the person at the checkout counter.
- How do you feel?
- How does the other person react?
Learning to pay attention to the subtle yet powerful differences can completely change how people respond to you in social situations.
Part 7 – Take Your Social Skills to a New Level
It’s time to put your new social skills into action.
You’ve learned how to be more confident and taken your social skills to a whole other level. So what’s next?
Look for new opportunities to test what you’ve learned. Remember, social skills are learned, and they get easier with practice.
So put yourself into situations where you can try making small talk, play confidencebuilding games, and confidently engage people in group conversation.
As you become more fluent in social situations, the rewards can be huge — from simply being more comfortable around people, to meeting a new circle of friends, to accelerated progress in your career.
Want even more help taking your social skills to the next level? My How to Talk to Anybody program gives you the mindsets, strategies, and word-for-word scripts to easily strike up conversations with anyone, anywhere, without the fear of running out of things to say. You’ll build deeper connections with the friends and co-workers already in your life.