⭕️ How to Start a Conversation (Without Feeling Awkward)

Hey friend,

If you’ve ever been at an event, standing awkwardly with a drink in your hand, pretending to text because you have no idea how to start a conversation—same.

Over the past few weeks, I’ve been to several events, and even though I literally speak for a living, I still find it uncomfortable to randomly walk up to people and introduce myself.

And I noticed I wasn’t the only one.

Most people, especially our generation, struggle with this. The stats even back it up—67% of Gen Z believe you don’t have to meet in person to build a professional connection​.

Which makes sense. We grew up in a digital-first world. Post-COVID, social skills feel rusty, and networking can feel more draining than exciting.

But here’s the truth:

The relationships that actually move your career, business, or mission forward? They’re built IRL.

So if you want to succeed as a Leader of Today, you’ll have to learn how to meet people, build relationships, and create your own opportunities.

That starts with one thing: knowing how to start a conversation.

read time: 6 mins

p.s: seems like a lot of emails are still not getting delivered, do you mind making sure you move this to your primary inbox, click any link on the newsletter and reply with “Hi Ziyaan” - will be super helpful

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Why Starting Conversations Feels So Hard

Let’s be real—talking to people shouldn’t be this hard.

But between social anxiety, overthinking, and the fear of rejection, most of us make it way more complicated than it needs to be.

Some common thoughts before approaching someone:

• What if they don’t want to talk?

• What if I say something weird?

• What if I run out of things to say?

But here’s something I realized:

Most people at an event feel the exact same way.

They’re also looking for someone to break the ice. They’re also hoping to meet interesting people.

So if you take the initiative, you’re already winning.

The 3 Levels of Conversation Starters

Not all conversations start the same way. Some situations call for quick and casual openers, while others need deeper, more meaningful entry points.

So here’s a 3-level framework you can use for any event, networking situation, or social gathering.

LEVEL 1: The Easy Openers (Low Effort, Low Risk)

These are quick, simple, and effective. Use them when you don’t know where to start.

• Hey, I don’t know many people here—mind if I join you?

• What brought you to this event?

• Have you been to an event like this before?

• I just heard someone mention [random topic]. What’s your take on that?

• I love your [shirt/bag/shoes]. Where did you get it?

• What’s been the highlight of your day so far?

• Who’s been the most interesting person you’ve met today?

• Do you think [event speaker/topic] lived up to the hype?

• What’s one thing you’re hoping to get out of this event?

• I feel like everyone here is way more put-together than me—do you feel that too?

• I know we just met, but do you think we could survive a zombie apocalypse together?

• What’s the best thing you’ve eaten today?

• If you could only listen to one song for the rest of your life, what would it be?

• What’s your go-to fun fact about yourself?

• Are you more of a ‘walk up and introduce yourself’ person or a ‘wait for someone else to start’ person?

LEVEL 2: The Engaging Hooks (Medium Effort, Builds Momentum)

Once the conversation is flowing, level it up with something more engaging and unique.

• If you could invite one person (dead or alive) to this event, who would it be?

• What’s a project or passion you’re working on that excites you?

• What’s the best piece of advice you’ve ever received?

• If you had to describe your job using only emojis, what would you use?

• What’s a skill you wish more people had?

• If you could teleport anywhere right now, where would you go?

• What’s a random fun fact that always blows your mind?

• What’s the most unexpected path that led you to where you are today?

• If someone made a movie about your life, what would it be called?

• What’s something you’ve always wanted to learn but never got around to?

• If you could swap lives with anyone for a day, who would it be and why?

• What’s something that instantly makes you respect someone?

• What’s a trend or habit you think we’ll look back on in 10 years and laugh about?

• If you could have dinner with your past or future self, which one would you choose and why?

• What’s a book, podcast, or article that recently changed your perspective on something?

LEVEL 3: The Deep Dive (High Effort, High Impact)

If the vibe is right and you’re connecting, go beyond small talk with deeper, thought-provoking questions.

• What’s one belief you’ve changed your mind about in the past year?

• What’s something you’re incredibly passionate about but rarely get to talk about?

• If you could design your perfect life, what would it look like?

• What’s a lesson life keeps teaching you over and over?

• What’s the hardest decision you’ve ever had to make?

• What do you think people misunderstand about you?

• If money wasn’t a factor, what would you be doing with your life?

• What’s been your biggest win and biggest challenge this year?

• If you could go back and give your younger self advice, what would it be?

• What’s something that makes you feel truly alive?

• What do you think the world needs more of right now?

• Who has had the biggest impact on your life, and why?

• What’s a random thought that’s been on your mind lately?

• What legacy do you hope to leave behind?

• What’s a defining moment in your life that shaped who you are today?

Bonus: How to Exit a Conversation (Without It Being Awkward)

Not every conversation will be a hit. Some will feel forced, or you’ll just need to move on.

Here’s how to gracefully exit:

• It was great chatting with you! I want to meet a few more people before the event ends, but let’s stay in touch.

• I’m going to grab a drink/refill. Want to come with me?(If they say no, you’ve exited.)

• I just saw someone I need to say hi to—let’s connect later!

• Hey, it’s been awesome talking! Before I go, do you have a LinkedIn or Instagram?

• I have a feeling I’ll regret it if I don’t go introduce myself to [person/speaker]. Wish me luck!

Friend, today will mark my sixth consecutive week of sending this newsletter - we truly are on a winning streak. If you have been here for a while, you know I have struggled with consistency. Just want to say it brings me so much happiness and fulfilment to have the privilege to write to you each week. Truly - it means the world. Thank you for supporting me - if there’s anything I can do for you, literally anything. An intro to someone, a shoutout or just a sound board on a call - don’t hesitate to reply to this email and let me know - I reply to every single email from the community.

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