How most people botch a conversation (and how to fix it)

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Candidate,

There are certain truths in life that NOBODY TELLS US. In fact, we're actively misled:

Truth #1: Being nice, alone, doesn't make you attractive
Truth #2: Saving money on $3 lattes and $5 appetizers is pointless
Truth #3: Just being good at your job isn't enough
Truth #4: Buying a house is not the best investment
Truth #5: College isn't for everyone

Yesterday, I told you about a wedding where, years ago, my awkward conversational skills sucked the energy out of the group.

What did I do wrong?

I was asking question after question, thinking I was being polite ("Ask questions! People love to talk about themselves!"), but I didn't know something critical.

Here's a truth nobody tells you about mastering conversational skills: ASKING TOO MANY QUESTIONS IS JUST AS BAD AS NOT ASKING ANY!

Asking questions is a great way to connect with people: True — but INCOMPLETE.

You'll notice that novices often pepper people with questions, making it feel like an interrogation (something I was guilty of for a long time). I call this TMQ Syndrome: Too Many Questions.

"So where are you from?"

"Do you like it?"

"What brought you here?"

"Do you like this wine?"

"How did you get your hair to grow so long without getting split ends?"

"What's your workout?"

OMG, ENOUGH!

Anything else you'd like to tell me?!

BAD advice: Ask questions all day long!
GOOD advice: Add value by asking questions — but also sharing something about yourself. That's how you have a balanced conversation, not a monologue or an interrogation.

It's interesting that we're taught to be better conversationalists by asking questions … but rarely told that asking too many questions is intrusive and off-putting. The truth is, sharing your opinion is how you "carry" your side of the conversation and give them a chance to learn about you.

If you've ever wanted to stop being awkward and talk to anybody …

The first thing to do is NEVER EVER look at 99% of the advice about mastering your conversational skills unless you want to embarrass yourself.

Like this example:

Barf.

It's funny how we think that people should just love us for who we are. WRONG.

You could be the greatest, sweetest, most amazing person … but it's YOUR responsibility to communicate that. If you can't, you lose.

"But Ramit," whiners say, "you're telling me to TRICK people. Ugh! That's so dishonest! They should see me for who I am. I shouldn't have to change."

Real talk: It's not shallow to improve your presentation. In cooking competitions, presentation is half the grade. And if you're honest with yourself, you judge other people for how they look and how they make you feel, so why wouldn't you expect others to do the same?

Another damaging myth about social skills is that you have them or you don't. Like brown eyes, or blonde hair — they're something you're just born with.

While some people are naturally more friendly, approachable, or comfortable in a crowd, social skills are just that — skills. Like shooting a basketball, playing the violin, or baking the perfect cherry pie — with practice, anyone can improve.

Nobody knows this better than me.

In my early 20s, I could have given a masterclass on how to be insecure and socially awkward. Anytime I spoke to someone new, my palms would sweat and I'd be desperately searching for the exit. I hated feeling that way and knew that if I didn't change something, life would pass me by. So I started collecting tools that would help me break out of my shell a little at a time.

One tool that really helped me was something I call the Question Toolbox.

The concept is simple. I would jot down great questions that I'd hear others use in social situations — questions that started conversations, rather than the tortuous, cringey carnage my interrogations were bringing.

Being a systems nerd, I categorized them for different scenarios and different settings so I'd always be prepared no matter what situation I found myself in.

Like a cheat code for social skills.

For example, here are a few of my favorite icebreakers you can try next time you get stuck.

Networking events/industry conventions

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

Dates

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

Baristas/Wait staff

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

Since I started using the Question Toolbox, I've found social gatherings more enjoyable — fun even! By keeping a few of these in your figurative back pocket, you'll never run out of things to say and will always feel like you're in control. No more sweaty palms and planning your escape route.

And that's just one tool of the dozens I've collected.

If you'd like access to all the tips, tricks, and reliable strategies I've learned over the years, check out my social skills course, How to Talk to Anybody.

You'll discover the exact methods that have helped me (and thousands of others) go from awkward and antisocial to being able to work any room with class, comfort, and confidence.

This works in-person and online.

Look, Candidate, social situations don't have to be scary. And learning how to be more likable isn't as hard as you might think. Inside How to Talk to Anybody, you'll find easy, low-risk ways to progress as fast as you're comfortable. Before long, you'll be looking for social opportunities to show off your brand new set of skills.

Don't make the same mistake I did and watch another minute of life pass you by. You owe it to yourself to at least check it out. You have nothing to lose and a wide world of possibility to gain.

Here's the link again.