TL;DR: The easiest way to connect with anyone at an event intern or CEO is to match your questions to their career stage. Juniors light up when you ask about their dreams: who they want to meet, what would change everything. Executives open up when you invite them to reminisce: favorite memories, how the dots connected. Meet people where they are.

I was standing on a balcony in Cannes during Cannes Lions the networking Olympics watching thousands of brilliant people walk right past each other without saying a word. Not because they didn’t want to connect. Because nobody ever taught them how to start.

So here’s the entire framework. One sentence: juniors want to dream, execs want to reminisce. Get that, and you can walk up to anyone an intern or a CEO and have a real conversation in under a minute.

What’s the easiest way to start a conversation at a conference?

Most people open with “So, what do you do?” It’s fine. It’s also forgettable. That question puts all the work on the other person and leads nowhere interesting.

Try this instead. Figure out roughly where someone is in their career, then ask the kind of question that stage of life actually wants to answer. People early in their careers are looking forward. People deep into theirs are looking back. When your question matches their direction, the conversation flows on its own.

This is the easiest way to connect with someone, whether they’re an intern or the CEO.

No pitch. No performance. Just curiosity pointed in the right direction.

What should you ask someone early in their career?

Juniors want to dream. They’re full of ambition and short on access. The best thing you can do in a conversation is take their ambition seriously. Ask forward-looking questions like:

• Who’s someone in this industry you really want to meet?

• What’s the one thing that would change your career instantly if it happened?

• Where do you want to be in five to ten years?

Notice what these questions do. Their manager asks them about output. Their peers talk about survival. Almost nobody asks them about the future they’re trying to build. You just became the person who did and they’ll remember you for it.

And if you’re the junior in the room? These questions work on other juniors too. Dreaming together is exactly how strong peer networks get built. The people next to you now are the executives you’ll want to know in ten years.

What should you ask an executive or senior leader?

Flip the script completely. Execs want to reminisce.

Think about it. They have the title, the recognition, the track record and almost nobody asks them about the journey anymore. Everyone in the room wants something from them. Almost nobody is simply curious about them.

So give them the opposite of a pitch: an invitation to look back.

• What’s your favorite memory from this event over the years?

• Looking back, how do the dots of your career actually connect?

• If there were a documentary about your career, what would the title be?

That last one always lands. It gives someone who’s spent decades being serious about their career permission to be playful about it for a minute. You’ll hear stories they’d never tell on a panel and you’ll learn more in five minutes than in an hour of small talk.

Why does this framework work on everyone?

Because it’s not a trick. It’s respect.

You’re not working an angle. You’re showing someone that you see where they are. A junior who’s dreaming doesn’t need advice from a stranger they need someone to treat the dream like it’s real. An executive who’s seen everything doesn’t need your elevator pitch they need one genuine human moment in a day full of transactions.

Here’s the part nobody mentions: this takes the pressure off you, too. You’re not performing. You’re not “networking.” You’re just being curious in the right direction. That’s a skill you can use at a 10,000-person conference or a 20-person meetup.

For my fellow firsts the first in your family to walk into rooms like these this matters double. You don’t need a fancy title or a big network to start conversations. You need good questions. And now you have them.

Key takeaways

• Juniors want to dream: ask forward-looking questions about who they want to meet and where they’re headed in five to ten years.

• Execs want to reminisce: ask about favorite memories, how their career dots connect, and what their career documentary would be titled.

• Match your questions to someone’s career stage and the conversation takes care of itself.

• Retire “so, what do you do?” ask something the other person will actually enjoy answering.

• Curiosity beats pitching every time. Nobody remembers your elevator pitch. Everyone remembers feeling seen.

FAQ

What is the best opening question at a networking event?

Skip “what do you do?” and match your question to their career stage. For someone early in their career, ask who they want to meet or where they want to be in five years. For a senior leader, ask about a favorite career memory. One thoughtful question beats ten minutes of small talk.

How do you approach a CEO without being awkward?

Don’t pitch them they’re pitched all day. Instead, invite them to reminisce: ask how the dots of their career connected, or what the title of their career documentary would be. Genuine curiosity about their journey is rare, and it stands out.

What questions should you ask junior colleagues at events?

Ask forward-looking, dream-oriented questions: who they want to meet in the industry, what would change their career instantly, and their five-to-ten-year goals. Taking a junior person’s ambition seriously is one of the fastest ways to build a real connection.

What if you can’t tell how senior someone is?

Default to curiosity and let them steer. Start with a forward-looking question if they answer with decades of stories instead of dreams, follow their lead and switch to reminiscing questions. The framework still works; you just calibrate in real time.

Keep going

• My AI networking follow-up system what to do after the conversation ends: how I capture every contact at an event and follow up two weeks later without losing anyone.

• How to set up your LinkedIn so recruiters find you the profile basics (headshot, cover photo, keyword headline) that turn connections into opportunities.

Want more frameworks like this? Follow @careercolin on Instagram I break down one career idea at a time, built for firsts.

Colin Rocker is a Forbes 30 Under 30 creator, LinkedIn Top Voice, and founder of For The Firsts, NYC’s monthly meetup for first-generation professionals.