10 Prompts for Deeper Conversations with a Friend or Colleague

Have you ever felt like you want to get to know someone better, but you just have no idea where to start?

In life, it’s safe to say we’re going to meet and interact with all different kinds of people…

On a few lucky occasions, we’ll come across a person that we get along with right away. Usually we know this because our interactions with this person provoke a feeling of trust or comfort. It feels almost effortless to get to know the person, and equally effortless to share personal details about our life…

On the other hand, there are times when we know right away that we are not compatible with someone. Maybe their core values or views conflict with our own, or maybe it’s as simple as their tone of voice just rubs us the wrong way…

But what about the people that we just simply want to get to know better? Maybe you have a hunch that you’d really enjoy someone’s company… but it’s hard to bridge the gap between the niceties of “Hey, how’s it going?”, “I’m fine. How are you?” to “Hey, did you end up deciding to take the day off to visit your cousin in the hospital? I’ve been thinking of you both…”

A client of mine actually reached out to me the other day asking for some ideas on how they can create deeper conversation with their colleagues on a weekend trip they were about to embark on…

And this got me thinking…

When looking to have a deeper conversation with someone, where do you start? Obviously you don’t want to scare anyone off by probing if they’re not very comfortable with you yet, but at the same time, maybe that’s the person who could really stand to gain from opening up about their life. What’s more, sometimes I find that it’s almost easier to confide in a person you don’t know very well, compared to confiding in a spouse or a family member.

In search of how to aid my client in their request, I came up with a list of 10 different ways to invoke deeper conversation with someone:

1) Have each of you make a list of the things that you’re most curious about the other person then take turns answering questions about their area of interest

2) Each of you shares one regret you have in life and what you learned from it (repeating as many times as you please)

3) Each of you writes down 5 answers on individual pieces of paper (answers that involve simple ideas or concepts) then, place each paper into a hat and take turns drawing an answer and trying to come up with the question that you think your answer is responding to.

4) Time Machine Time! Share something about who you were or what your life was like starting at age 5 and working your way up to your current age in increments of 5 years. (What was life like at 10 for you? 15? 20? And continuing on…)

5) Talk about the future you see for yourself and the future you see for your kids. What will the world be like for them and how might you help them prepare for it?

6) Talk about what you love about your romantic partners and what you want to learn to love and accept more of.

7) Discuss what you are most grateful for.

8) If you could change something about the way you were raised, what would it be?

9) Each of you choose one problem you are currently facing, then take the time to share, discuss and reflect on them together.

10) Throw all these questions away and simply ask in each moment what could I say that’s more true? What could we talk about that would matter more? What am I hiding or holding back? What if I shared more of my heart in this moment?

The beautiful thing about this process isn’t just that you’re about to gain a new friend! You also stand to gain from being vulnerable with this person, and will learn more about yourself through these conversations!

If you try any of these conversation-starters out, let me know how it goes!

Happy conversing!