People enjoy your company when they enjoy being with you, and they enjoy being with you when they feel comfortable speaking about themselves openly to you.

 

It should be clear that the focus is on the other person and not you. It is, therefore, almost a sin to talk about yourself when you haven’t been asked a question if your intention is to build a good relationship with another person. If you want others to like you, have them talking about what interests them the whole time.

 

People normally enjoy reflecting on ‘what if’ scenarios in their head. Pondering these scenarios takes them on a journey through their imagination, which is not only fun because it tickles their curiosity, but also productive as it helps them discover themselves. Therefore, the trick to having other people enjoy being with you is to choose the right question at the right time and taking them on this little voyage through their imagination. They must feel like they are the captain of their ship, and you should be the compass that guides them through a pleasant conversation with your questions.

 

These questions must be light enough to be used at a casual cocktail party, but also require enough depth so that you don’t come across a boring. Below, I’ve picked 3 questions that you can ask that focuses on the the person’s future, past, and present that will guarantee that you two have a great time together.

 

For these questions to be most effective, the setting is important. I would recommend that you create an environment in which the other person feels safe and at ease—think of 1 on 1 setting in a cozy coffee shop or bar on a rainy day, rather than at the club with David Guetta blasting full on in the background.

 

With that said, let’s jump right in.

 

 

1. FUTURE: What do you want to do in 10 years if you had enough time and money to do anything?

 

Nobody knows what is going to happen in 10 years. Maybe the polar ice caps melt and we as a civilization struggle to stay afloat, or maybe you might hit the jackpot in the next lottery and spend the rest of your days on Bali’s sunny beach. 10 years is far enough in the future that keeps things nicely vague, so regardless of the reply the conversation would be nice and light.

 

This question allows the recipient to explore their personal ambition. We often live too much in the present, bogged down by our day-to-day responsibilities, that we forget what is possible. By unburdening yourself from the chains that tie you that today, you allow the listener to look into her best life—and who doesn’t like to think about that?

 

The true beauty of this question is that you have no idea what the reply is going to be. However, I can guarantee you that the reply will be interesting as everybody has some kind of dream. Finding a follow-up question would be a walk in the park and 30 minutes to an 1 hour later you might be having one of the deepest and most meaningful conversations of your lives.

 

 

2. PAST: If there is 1 thing that you could tell your younger self, what would it be and why?

 

I love this question. I picked this question up in an interview with Dominic Barton, former Global Managing Partner at McKinsey, a consultancy. During his time as Global Managing Partner, he called 2 global leaders every day and asked: “if there is 1 thing you could tell your younger self, what would it be and why?”

 

Though the replies Dominic received from global leaders were mostly business related, I’ve discovered that the same question can be asked to everyday people and trigger very interesting conversations.

 

This isn’t a question you can reply to at once because it restricts the person to choose only 1 thing. You also have to think deeply into what ‘younger self’ means. Is it 1 year ago? 10 years? 30 years? As you can see, it will take some time for the recipient to get to a good answer.

 

What is amazing about this question is that you get to listen to the deepest regrets and fears of the recipient without directly asking for it. You have the first seat ticket to discovering an event that is very close to her heart of the recipient. Therefore, it is important that you are responsible for the tone of the conversation: sincere, candid and genuine.

 

There are many ways you can carry this conversation. Depending on what story your partner shares with you, you yourself can share a similar story of your own, or you could ask follow-up questions to dig deeper on why she thinks or feels the way she does. You just need to make the sensible decision to know which path to take.

 

 

3. PRESENT: What could constitute a perfect day for you?

 

I discovered this question from an article in New York Times called “The 36 Questions That Lead to Love“. Actually all the other 35 questions are wonderful, so please feel free to go through the entire list and choose the ones that you find most interesting.

 

The questions in this list are tagged as ‘the ones that lead to love’ but they can be applied to anybody whom you would like to build a positive relationship with.

 

“What could constitute a perfect day for you?” is a question that looks into where your listener is currently in her life. A perfect day seems trivial, but this question provides a window into what the recipient considers ‘perfect’. For some people, this might mean waking up well rested and having a well toasted slice of bread so that butter can be spread smoothly across one side, and for others it might be getting a plane ticket and going to the Alps for skiing.

 

By understanding what your listener enjoys and wants, you can find connections with yourself or dig deeper into their passions and encourage them to share more about themselves. Always remember that the more you allow the other person to speak, the better conversationalist you will become.

 

 

4. TLDR,

 

If you want to become a good conversationalist, the conversation should always revolve around the other person’s interest. This can be done by asking the right questions, some of which we have uncovered today.

 

To have your partner lighten up and excited, ask them: “what do you want to do in 10 years if you had enough time and money to do anything?”. You will be able to listen to her biggest dreams and ambitions.

 

If, however, you would like to talk on a more serious note and do not mind being vulnerable with your partner, then ask “if there is 1 thing that you could tell your younger self, what would it be and why?”.

 

Lastly, if you would like to keep the conversation on a lighter tone and explore what she likes or dislikes right now, ask “what could constitute a perfect day for you?”

 

Are there any other questions that you found helpful to keep a good conversation going? If so, please share with me in the comment section below! I would love to hear your thoughts 🙂