How to Have Deep Conversations

New week – New challenge! This week we’ll be focusing on having great. Deep and meaningful conversations. Now since I’m no expert, I’ll present 3 expert tips that gives the most bang for your buck when it comes to getting better at deep conversations. I will also outline a clear implementation strategy for the week ahead. YouTube how-to videos in all its glory, but it won’t magically transform you unless you put in some real effort, and a good strategy is half the battle.

But why all the effort? Just imagine yourself being able to truly connect with people, being so caught up in a conversation that time isn’t present anymore. I’m sure you’ve experienced it. If not, it’s about time. More to it, the better you get at this skill, the quicker will you be able to reach this state. Creating special bonds with people you’ve just met is kind of a thrill. It’s Almost addictive. Perhaps you have friends you’ve known your entire life, but never really got through with. Perhaps this will enable you to finally crack the code. Connecting and being more likeable and remembered will favour you in so many ways. Doors and opportunities you can’t imagine will open.

As an example, I can just mention what happened to me this morning when I was down at the gym. There’s a super nice lady that always works out the same time as me on Sundays. And a few week’s back I complimented her for always being so happy and dancing around while resting between sets. Gradually I’ve gotten to know her better, applying all these conversational skills. And this morning when I was about to say goodbye and leave, I told her to have a great day and keep making people smile. But before I had the  opportunity to leave, she asked me if I was single.. Pausing for a second before answering, trying to figure out if she was hitting on me or not ( she’s 50+).

“Yes I am”

She then said that she had a perfect girl she wanted me to meet, and invited me to a Sunday dinner a few weeks from now, where she will to introduce me to this girl. We’ll see how that goes, but the point being – if you’re able to have good conversations and just talk to people without any hidden agenda but because you enjoy it, it will give you so much in return. AND, you’ll start to enjoy it the better you get at it. I know because I used to dread conversations like these, bus as I’ve improved – I now crave them.

But deep conversations don’t happen without first establishing some rapport and progressively deepening the connection. If this is all distant to you perhaps you should go back and look at the previous two week’s challenges, since this is the third and last part of how to develop conversational skills. It started with approaching people and striking up that initial conversation, and we then moved on to more surface level conversation techniques, but still highly usable in a deep conversation context.

But so – just as last week – these tips I’ll be sharing are hi-jacked from Improvement pill’s YouTube channel. That means I don’t own any rights to the videos, I just use it for the purpose of education and don’t make any money out of it. I do recommend you to go check out his channel as it holds a ton of value. Link to the original video can be found here (LINK – Communication Skills – Deep conversations).


  1. SHARING – Share and be vulnerable, by opening first you will make the way for the person you’re talking to also share something deep. Link to where this is talked about in the video:
  1. LISTENING – A key feature to be trusted with continues sharing from there part, is to make them feel that they really are being listened to and have your full attention. Link to where this is talked about in the video:
  1. RELATING – Being able to identify what emotions the other person conveying, so that you can relate and follow up by sharing something similar. Link to where this is talked about in the video:

The objectives

Once a day, Monday through Friday, aim to have at least one conversation lasting at least 15 minutes to enable you to build enough rapport to go deeper. I know from experience that this won’t happen if we don’t plan and schedule it. Everyday life will happen, and yeah You’ll just “do it” tomorrow instead. For me, this means I’m going to schedule 2-3 face-to-face interactions, and have a long phone call or Skype conversation the other days. I’m going to shoot for 30 minutes. Important is to not jam it all into one day, daily is key for efficient progress so we can evaluate, tweak and improve while it’s still fresh.

Good Luck, and commit to me if you really want to do this!


About the author: alenils

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