How to Push a Conversation Forward

“How can I push a conversation forward when I’m shy?”

I hear this sentiment a lot from my shyer clients. They look at someone else more outgoing and wonder “Why not me?”– and all that does it build a bigger gap. That’s speaking with distancing language after all.

Don’t do that.

Set your sights on closing the distance. No matter whatever innate talents you are (or aren’t) born with, you can still cultivate skills. You can reshape weaker abilities. Building habits is the cliche term, but let’s just say you need to create new tendencies.

At this moment, maybe you tend to freeze up or shut down in certain social settings. There’s a limited or complete lack of movement. For a conversation to flow, you need to open up to the idea of movement.

Without any movement, there isn’t going to be any interaction. No interaction means no conversation.

The first and most basic movement for communication is the push.

Push to Reach Out

Many people who come from an introverted background will overthink the push:

  • This means I have to be on the offensive.
  • Pushing means I have to be aggressive.
  • The bottom line is I need to attack this conversation.

Those are all possibilities because there are many different ways to push:

  • You can push a door open.
  • You can slam a car door.
  • You can shove your clothes into a bag.

Not every push needs high energy. In fact, it’s even better when little thought is given to it– just like how you usually give little to no thought when pushing open a door.

A push can just be a push.

You don’t even have to think about extending your arm. You don’t think think about placing your hand on the door. Your mind is already thinking ahead about all the stuff you need to do once you’re on the other side of the door. (Like, where the hell did you park?)

Instead of stressing over how much energy you need to bring to your push, simplify the movement to reaching out. In terms of speaking then, you’re not worried about the “perfect” greeting or opening– you just open yourself to making more attempts to engage.

You don’t overthink the outcome. You don’t overthink how well it goes. You (slowly) take yourself from the passenger seat to the driver’s seat.

Push to Initiate

You know how cars these days have a push-start? Same concept: you push to go. With a presentation, whatever you “put out” in the introduction can be considered a push.

  • When someone interrupts you for direction? That’s a push to find help.
  • Whenever someone has a question in general? That’s a push for you to follow up.
  • Without a push in these instances, what would happen? Nothing.

Push to Follow Up

Remember that the same movement people use to ask you can be your movement as well. When a conversation is interesting, you usually want to keep it going, right? So what do you do? You do some kind of follow up.

Maybe the follow up is a comment. Maybe the follow up is a question. Sometimes if you don’t initiate the push here, the other person can mistakenly think you’re not interested. Then, the topic changes.

Unnatural Pushes

Be sure to implement these concepts at your own pace.

Opening yourself to be more proactive is good. However, you don’t have to force yourself to push all day, everyday. There can be a downside so pushing just for pushing’s sake:

  • People follow up on things they don’t really care about.
  • People ask way too many questions unnaturally, making it feel more like an interrogation.
  • People end up making the interaction one sided.

Those points serve well to remind us that the art of conversation requires a delicate balance of selfishness.


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Published by Jon Dao

Formerly, the Conversation Coach

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