Readers will be surprised to hear that I wasn’t always the charming, hilarious, and stylish personal finance expert they know now.

In fact, I was so awkward, I made Urkel look like Robert Downey Jr.

(Not pictured: Someone who isn’t a completely awkward mess.)

I had no idea how to talk to people. I remember I once talked to someone on the phone and spent a solid TWO MINUTES talking. After I finished, the other person just paused for what seemed like forever before saying, “So…what exactly do you want?”

And I had NOTHING to say.

You’ve probably been there before:

• You walk up to a group of friends talking. Stand there awkwardly while waiting for one of them to notice you. Wish for death.
• You start telling a story to a group of people and — in the middle of it — realize the story sucks. Continue anyway.
• You go to an event and instead of meeting people, pull out your phone and furiously check email.

The good news is being able to talk to people and hold an engaging conversation is a SKILL — and like any other skill it can be learned, honed, and mastered.

A while back I got a question from an IWT reader named Emily. She asked:

“How do you approach companies/or anything else when you don’t have any confidence? I seem to go mentally blank. And the words don’t come out at all. Backwards and not in order.”

It’s a fascinating paradox. With your friends, you tend to have the BEST stories but if you just met a group of people, all of a sudden your mind goes blank and you have nothing to say. Most people are willing to say “that’s how it is,” but you can actually be able to treat this with systems.

Today, I want to teach you a system that’ll help you talk to people and NEVER run out of things to say. All you have to do is craft a Toolbox.

Crafting your social toolboxes

Before you start to brush up on your carpentry skills, you should know that I’m talking about more figurative toolboxes — but just as useful as their physical counterparts.

They are your:

1. Story Toolbox
2. Question Toolbox

At their core, your two toolboxes are documents wherein you write down all of your interesting stories and questions that you can have “ready-made” to share with friends and strangers at dinners, the bar, or even a job interview.

Once you start filling in your toolbox, you’ll start to realize that you’ll never run out of things again as long as you keep them handy.

How to make a Story Toolbox

I’m a firm believer in the idea that telling a Story is the best way to engage someone. It doesn’t matter if you’re with your friends or if you’re trying to sell a product. A good story can make a world of difference when it comes to building a good first impression.

That’s why you always want a large well of great stories to draw on.

You can create your Story Toolbox using any tool you prefer such as:

• Google Docs (what I use)
• Microsoft Word
• Microsoft Excel
• Evernote
• A physical notepad

It doesn’t matter what you record them with as long as you ARE recording them.

These stories could be funny, entertaining, or serious — and you might actually want to organize them as such.

Action step: Create your Story Toolbox

Designate a place to put your stories, and start by adding five of them.

If you can’t think of five good stories, think back to the last time you hung out with your friends or family.

What did you talk about? What made everyone laugh? Every family has an embarrassing/hilarious story. What is it for your family?

Hang out with your friends or family in the next few days, and write down the things you naturally talk about. This will help seed your Story Toolbox for the first time.

How to make a Question Toolbox

If you want to keep the other person you’re talking to engaged, there’s no better way to do it than with a thought-provoking question. It helps you always have something to say and talk to someone you don’t know.

Of course, depending on the context of your conversation, you’re going to want to have different questions for different scenarios.

I remember once, my friend noticed me checking this girl out at a bar, so he goaded me into talking to her. So I approached her and this exchange went down:

Ramit: Hi, I’m Ramit.

Woman: Hi, I’m [whatever].

Ramit: You look like a vodka soda girl. (I know, I know. I don’t know where this horrific line came from.)

Woman: …no.

I was surprised by how she just shut me down, so I decided to have some fun.

Ramit: Aw, c’mon. I’ve been right 100/100 times for the last 5 years. How are you going to break my streak like that?

Woman: I’m a recovering alcoholic.

Shortest. Conversation. EVER. But a funny story now.

If instead, I came in with my question toolbox filled with questions that weren’t awful pick-up lines, I might have had better luck. That’s why you’re going to want to craft different meaty questions for different scenarios.

Action step: Create your Question Toolbox

So the next time you’re making small talk, take note of great questions you hear and ask. Save them in your Question Toolbox for later.

Here are a few good sample questions to get you started:

Networking events/industry conventions

1. What made you decide to do X?
2. What are the biggest challenges when it comes to your industry?
3. If you had to do X again, what would you do differently?
4. As you gained more experience in X, what became more important and why?
5. What would make today/this event successful for you?
6. What still surprises you about X?

Dates

1. What are your biggest goals right now?
2. How do you spend your time?
3. Playful questions like: Which do you like more — pancakes or waffles?
4. What do you hate most about dating? (This question is both interesting and can help you avoid doing the thing they hate.)
5. What’s your favorite restaurant in the city? Why?
6. Which Spotify playlist is the soundtrack to your life?

Baristas/wait staff

1. What’s your favorite thing on the menu? Why?
2. What’s the craziest thing someone tried to order this week?
3. Have you ever written somebody’s name wrong on purpose because you didn’t like them?

BONUS: If you really want to exercise your social muscle, check out my video on improving your social skills. It’s less than 30 minutes.

Enhance your small talk

Small talk is a CRITICAL part of life and building relationships — it’s what helps people get to know each other, establish meaningful connections, and lay down the foundation for great long-term relationships.

The term “small talk” is actually a complete misnomer because of its HUGE impact on forming relationships and developing unshakeable confidence. As such, it takes a lot more care and nuance than just getting right down to the point.

If you walked right up to a CEO you admired at a mixer or convention and said, “I REALLY LIKE YOU. GIVE ME A JOB, PLEASE!” how do you think she’d react? She probably wouldn’t give you that job.

But if you went in with some care, and drew her into an amazing conversation and THEN asked her for a job (or better yet just advice or a coffee meeting), she’d be a hell of a lot more susceptible to it.

The key is realizing that confidence and the ability to carry a good conversation are skills — and like any other skill they can be learned, honed, and mastered.

I used to feel uncomfortable and out of place during social events too — but over time, I’ve developed hacks for confidence in new situations.

I’ll show you exactly how I do it in these 3 short videos. Just enter your email for instant access.

“Help! My mind goes blank when I talk to people”: How to talk to people is a post from: I Will Teach You To Be Rich.