These Questions Can Help You Connect with People at a Deeper Level

Thomas Oppong
Dec 17, 2015 · 5 min read

“How in the world do I connect with this person at the event?” This is a common question when trying to relate to people at any place of gathering. Finding creative ways to engage in conversations and connect can become a bit difficult.

These are a few question that lead to a meaning conversation at meetings, networking events and generally at any place where you have to talk to people for the first time. They can help you break the ice with a stranger.

Try these questions next time you’re at a party or a trade show or any event. You’ll find yourself connecting with people at a deeper level than you ever thought possible.

1. What do you do for fun?

You won’t be the first person to ask that question. Someone may have asked you the same question in the past. But the point of any small-talk question is to lead into a conversation. If you or your new contact give answers like “I like to watch movies and play video games”, there won’t be much to talk about. Always follow up with leading questions. But don’t turn the conversation into an interview. Nobody likes that.

Passive hobbies are only interesting to people that share them. Stuff like watching movies, listening to music, watching football, etc. If you do something active, you can explain first-hand what you do for fun that isn’t just observing something else.

Most people don’t do a lot outdoors. And it’s always a bit difficult to talk about what they do for fun. If you don’t have any hobby that’s interesting, and you’re already lacking social skills, the blunt and honest truth is you’re probably not going to be interesting to people.

Get a new hobby you can talk about. But you don’t have to start a new hobby you don’t like. You should genuinely enjoy it to make it fun for yourself before you can even feel comfortable sharing it with others.

If someone asks you that question, don’t just answer; follow up with an anecdote, an interesting question, or anything else that doesn’t let the conversation lull.

If you can’t help but talk about things like movies or watching something for fun, follow up with details specific to you, then you’re not only showing that you really do care about those things, but you’re giving your conversation partner thoughts to follow up on.

Worry less about impressing people, and more about finding common ground. That’s the point of the question.

2. What are you most passionate about?

‘Passion’ is a word so excessively used and almost always blindingly paired with work. What you love to do can be very different from what you do for living. If you make your passion your business, you will probably never work again in your life. Everything will feel like fulfilment.

There is a lot be gained from doing what you love for work. When you are really happy doing something you love, there’s a hint of what you are passionate about right there.

This question can get people talking for a very long time. People love to talk about things they are passionate about. Your response doesn’t need to be focused on work, but it should demonstrate your ability to devote yourself to a particular task or hobby about which you are passionate.

When you’re asked what you are passionate about at a networking event or at other event, it’s a good opportunity to share hobbies, enthusiasms, or whatever is important in your life. You could even talk about projects you are working on apart from work.

If you are asking, you can follow up with other questions like: what caused you to become inspired by the topic/activity. Did you discover it on your own or was it the result of the modelling of others? Is there a greater motivation to act primarily for self- improvement or for the betterment of others?

These kinds of follow up questions can keep you talking about a single topic long enough to keep the conversation interesting.

But if they don’t know what drives them or, they won’t be able to answer you. If they do know what drives them, for whatever reason, they might not be comfortable with sharing with you.

But the one part you do have control of is what you ask after the initial question.

3. What are you most proud of in your life and career?

This question reveals your proudest achievements, and what you choose will reveal a lot about your values and what gives you satisfaction. If you asked what your proudest moments are, you could talk about work achievements, but don’t limit yourself — personal achievements can be just as important.

It really doesn’t matter what you choose, as long as you can explain why it gives you a sense of satisfaction and pride in what you have done.

Other notable ice breaking questions.

You can also start a decent conversations with, “What do you do?” and and you could end up talking about meaning, purpose, and passion. It depends on your follow up questions. Keep your questions open ended and you will be fine.
Follow up with why. When you ask “why”, that’s when you start digging beneath the surface into motivations, dreams, hopes, even fears.

But take note of this: Your “cliche” questions are not the problem when you are trying to start a conversation,it’s how you carry the conversation after, that’s important.True connections take time and effort and there are no simple or superficial questions that will help you forge a deeper bond with a person.

You best practice would be to ask questions about something you apparently share or someone you know and build on that background. Make an observation and ask for their opinion — good or bad. The observation can be bold, outrageous, or on any topic. Just saying “what do you think?” can start some of the most amazing conversations.

The author is the curator at Postanly, a free weekly newsletter that delivers the most popular and insightful long-form posts from top publishers.

A network of business & tech podcasts designed to…

Thomas Oppong

Written by

Founder @AllTopStartups | Featured at Forbes, BI, etc. I share practical tools for productivity, wealth, health and happiness at

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

Thomas Oppong

Written by

Founder @AllTopStartups | Featured at Forbes, BI, etc. I share practical tools for productivity, wealth, health and happiness at

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

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