How to Start a Conversation in 4 Steps

3 min read
15 Feb

WARNING: this 4-step guide will empower you with the tools you need to experience incredible conversations. 

Step #1: Why am I having this conversation?

A conversation is like a fire, it needs a good purpose to be worth the effort.

There are two broad types of conversations:

1)     Meaningful - When you converse to learn, discuss, debate, convince, inspire, and so on.  

2)     Meaningless - When you converse for the sake of avoiding awkward silence. 

If you understand your motives early on it will be easier for you to guide your conversations in a meaningful direction. 

Step #2: Who is my audience?

Pay attention to understand the deeper picture of the person you’re speaking with:

  • How comfortable is this other person with me currently?
  • Are they dressed conservative or adventurous?
  • Do I know the people they hang out with?
  • What topics do I think they would find interesting?
  • What kind of jokes and questions would they be comfortable with?

Note: don’t pre-judge them based on their appearance. Confirm your assumptions through conversation.

You must do everything in your power to make this person feel COMFORTABLE and ENGAGEDDoing so will pay huge rewards by earning likability and establishing strong rapport. I'll speak about these topics in a later article.

Step #3: What material do I have to work with?

You must consider what flammable material you have in your situation to start the fire. Look closely at your surroundings. If you can’t see enough tinder and kindling, then the fire is going to die before you can add more fuel.  

In non-bushman terms, if there isn’t enough situational stuff to comment on, compliment on, or question about, then developing follow-up questions to build the conversation's momentum will be challenging. 

The material that you can consider to spark the conversation with is stuff like:

(A) Do they have any cool gadgets?

(B) What are they wearing?

(C) What are they doing?

(D) Is there anything unordinary going on?

(E) What do they look interested in?

(F) What do you think they are feeling?

The health of the conversation depends on your ability to follow up on your ice-breaking remark.

Never expect the other person to carry the conversation if you’re the one who initiated it. You become the fire-fanner once you initiate a conversation; you’re the one who keeps it alive by asking follow-up questions. You take control and transition the conversation where you want it to go.  

A conversationalist will likely take control of the conversation by asking your opinions or questions about you.

Conversationalists are genuinely interested in learning about others. That’s why everyone loves a great conversationalist – you get to do all the talking when you’re around them. Plus, you don’t need to put much thought into where the conversation is going.  

Step #4: How do I start the conversation?

Three main tools you  use to spark the conversation:

1)     The Comment

2)     The Compliment

3)     The Question

Let's put these tools into action using the questions you asked yourself in question 3:


You asked yourself: (A) Do they have any cool gadgets?

Icebreaker: Wow – I’ve never seen one of those.

Follow-up: What can it do?

Follow-up: How much will it cost me?


You asked yourself:  (B) What are they wearing?

Icebreaker: I’ve never seen someone with running shoes that colour! I love those!

Follow-up: What site did you order them off?

Follow-up: Did they fit the way they were supposed to?

You asked yourself:  (C) What are they doing?

Icebreaker: Jeez, you’re a natural!

Follow-up: Where did you learn to do that?

Follow-up: How long would it take me to learn?

You asked yourself: (D) Is there anything unordinary going on?

Icebreaker: You can really pull that costume off!

Follow-up: What was the hardest part to put together?

Follow-up: Where did you get the idea from?

Note: always be able to justify why you like something. They'll think you're full of **** if you don't have a genuine reason. You'll instantly lose their trust.


You asked yourself: (E) What do they look interested in?

Icebreaker: That looks interesting! 

Follow-up: Have you ever seen one?

Follow-up: Do know anyone else here? I bet we could steal it! ;) 

You asked yourself: (F) What do you think they are feeling?

Icebreaker: You look like the happiest guy on this train!

Follow-up: What’s going on in your life that’s so great???

Follow-upDo you think it’s too late for me to get one of those too???

Note: avoid asking questions that have a one-word answer; a question answered with a single word will slow your conversation's momentum. Ask open-ended questions instead.

If you remember my last article, your message travels 10% through your words themselves and 90% through your delivery. Make sure you deliver with a smile and a friendly tone.  

Notice how I aim to develop two follow-up questions following my icebreaker to get the momentum going in the conversation. Once you have some momentum, it’s seamless to transition into something a little more meaningful if you like. 

It might take you a few moments of looking like a deer in headlights, but if you're willing to endure those, I promise you’ll be able to exploit any opportunity you want to start a conversation.

Remember: the best way to eliminate lingering awkwardness is to simply address it.

No one can flawlessly start a conversation every time. You will at one point or another say something awkward. It's okay! My style is to combat awkwardness by addressing it with humour. 

Making a joke about the awkward thing you said is a great way to show that you’re human and that you don't take yourself too seriously all the time. 

You will develop your own style as you encounter more scenarios.  

At the end of the day, there isn't always going to be the perfect moment to spark a conversation. 

Take a breath, have fun, and go for it :)

If you made it this far, you'll love my next article: 3 Secrets of How to Keep a Conversation Going

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