How to Master Conversational Skills

Conversational skills were not always my strong suit.
Maybe you can relate — I’d walk into a room, maybe do a quick circuit around it, and go stand awkwardly in a corner.


Not good.
But my pain can be your salvation. After crashing and burning enough times, I discovered conversational skills aren’t a super power that you have to be born with. Anyone can make interesting, comfortable conversation with complete strangers if they learn a few simple tricks.
Mastering these skills is what lets me frequently host events, speak in front of large crowds, and even make guest appearances on shows like The Today Show, Fox News, and CNN.

The myth of the “natural”

It’s fascinating to me that social skills are one of the most important skills we can develop — maybe THE most important skill — yet we rarely look at it as a teachable, learnable skill that we can improve on.
Instead we believe that some people are “naturals” at conversation.

Ugh. This guy.
The truth is, we all start at different levels, but everyone can improve their conversational skills. Master these 3 fundamentals and you can talk to anybody — no awkwardness required.

1. How to start a conversation
2. How to join a conversation in progress
3. How to hold a conversation

How to start a conversation

I’ve developed 3 scripts that work in nearly any situation. Notice how ordinary they are. That is intentional! The truth is, we’re not searching for magic novelty words. We’re simply looking for a way to connect and build rapport.

• “Hi. How’s your morning going?”
• “Hi. I don’t think we’ve met. I’m Ramit.”
• “Good morning. How are you?”

The value in these scripts is not in their novelty, but in their utility: You can use these, starting immediately, and see how they evoke positive responses in others around you.
How many times have we walked past doormen, bartenders, people on the street, baristas — using our headphones and phones — to avoid small talk?
We can change that starting today. It’s easy to nod and shrug and then go back to your same old patterns of behavior. But I want to challenge you to just a small baby step — say hello! Use just ONE of these openers to start a conversation with a stranger today.

TRY TODAY: Test openers in low-stakes environments
The general openers above are great “easy outs” when you’re struggling to think of something to say. They get you past the hardest part: the start. But, we can take this a step further with low-stakes experiments. Ideal situations include greeting the mailman, checkout clerks, or even customer service reps on the phone.
Servers and baristas are paid to be friendly, so this is a perfect low-stakes situation. Just be aware of your environment: For example, don’t make your first conversation attempt when there’s a line of 50 people behind you!
They’ll ask how you’re doing, and what you’d like to order. Instead of ordering your “regular” (in my case, a tall iced green tea, unsweetened), SMILE first, then try one of these instead:

• “What’s good? (Answer: “Everything!”) “No really, what do you get when no one’s looking?” From here, you can order their suggestion (“That sounds good, I’ll try it”) or stick to your usual (“Cool, I’ll have to try that next time”).
• Non-offensive, safe-for-work jokes like “Have you ever purposely misspelled someone’s name on the cup because you didn’t like them? Like, I’d totally spell my name ‘Raw Meat.”
• “Seriously, what’s the craziest order you’ve gotten this week?” Notice how “this week” helps them narrow down the question so they can answer it easily. You do not want to be asking deep philosophical questions at this stage of the game!

Smile and keep the tone light. This is fun! Treat it like a game and watch what happens.

How to join a conversation in-progress

Group conversations can be terrifying. We show up, we meet people we don’t know, and freak out. We tell ourselves things like, “I don’t know what to say. If I speak up, I’ll sound stupid. I should just be quiet and listen. Why would anyone listen to me?”
So today, let’s reframe how we think about group conversations. It’s not, “Why would anyone listen to me?”, but instead, “I have a lot of value to add. What’s the best way I can add it here?”
Here’s 3 ways to add value:

• Inject a fresh perspective into the conversation. When you are standing close by, say “I don’t mean to eavesdrop but…” You are acting as a “breath of fresh air” and adding value to a conversation that is already going on.
• Ask the questions everyone else is thinking. We naturally don’t want to ask for clarification. It makes us look dumb, we feel foolish, we wonder if we missed something that everyone else got. The tactic here is to think of yourself as the curious beginner. Someone’s talking about something and you say, “I’m sorry. I didn’t quite get that. What does that mean?” The curious beginner is not afraid to look stupid. They are actually making other people feel comfortable by asking the questions that everyone else wants answered.
• Give observational compliments. Another great way to join a conversation in progress is with observational compliments. Psychology shows us that we like people who like us. Complimenting someone in a thoughtful, authentic way can be one of the best things you do to become more likable. This is not as simple as, “Nice dress,” or “I like your shirt.” An observational compliment is something like this, “You know, you seem pretty adventurous. I know a lot of management consultants, and I don’t know any of them who would do scuba diving in their off time. Seems pretty cool.”

Hold the conversation

Asking great questions can be one of the best ways to ingratiate yourself with someone, particularly if there’s a silence in the conversation. As we’ve all heard, people love to talk about themselves. So if you can ask a very penetrating, piercing question, something that really cuts to the core of what they’re interested in, they’ll love to respond.
However, asking too many questions can be problematic. I show you what I mean (and how to strike that balance), in this 2 minute video:
Here’s a few examples of great questions that you can ask.

• “What made you decide to do X?”
• “What was the biggest challenge when it came to X?”
• “If you had to do X again, what would you do differently?”
• “As you gain more experience in X, what became more important and why?”
• “What’s been your favorite part about X?”

Notice that some of these questions are more appropriate for professional conversations. Others are appropriate for fun conversations. If I’m at a bar, I’m not going to say, “Tell me, what was the most interesting thing you realized about your career progression?”
That’s just weird. I might say, “What’s your favorite thing about eating in this city?”
Don’t think that you should only ask questions. Respond to their answers in a way that builds a connection. You want to share a little bit about yourself as well. You can talk about your background, your family, what you do for work, something interesting you discovered at work, something you’re struggling with that you’ve been trying to get a handle on for the last few months.

TRY TODAY: Tell more and better stories
Storytelling is the “invisible thread” that runs through truly great conversations.
If you watch someone who has great conversational skills, you’ll notice that not only do they ask questions, but they talk about themselves. Celebrities who go on those shows are, of course, inquisitive and friendly, but they’re there to talk about themselves in an engaging way.
Have you noticed how celebs always have fun, amusing stories to tell?
While it seems like these stories unfold off-the-cuff, they’re actually tested, refined, and practiced for months in advance. In fact, these stories often go through many iterations before they’re ever ready to be told in front of an audience.
Thousands of my students have used stories effectively to land their dream job, pitch clients, meet VIPs, or even make new friends.

I’ve put together a one-page checklist including the 5 steps to develop, refine, and tell compelling stories. You can download it below for free. In just a few minutes, you’ll be on you way to vastly better conversations.

Discover how to have great conversations using great stories