10 min read

How To Talk To Anyone

How To Talk To Anyone
Thank you to Alyssa, Eli, and Drew for being dedicated readers! I am immensely grateful that you even open my posts.

Today, we're going to turn you into a CONVERSATION GOD!

Talking to people can be difficult. But like any skill, with practice, you'll get better.

Always Prepare If You Can

What do I mean by prepare? I mean take the time, maybe 15-30 mins, before the meeting to do some light research on the person you're going to speak with.

Gather basic facts like:

  1. Where are they from?
  2. What do they do? (Work, hobbies, etc.)
  3. What do they talk about online (Blogs, tweets, etc.)
  4. Who do they follow?

Create A Mind map

I like creating mind maps of the people I speak with. This starts before we even begin. I try to piece together whatever information is available online into a "story". That way, I can infer what they're interested in now. And target that in our conversation.

A Practical Example:

I have an internet friend. Her name is Alyssa (also a dedicated reader of this newsletter). I'll use her as an example to highlight the process.

If I was meeting Alyssa for the first time, I'd first look at her socials.

So what can we see here? We can probably pull away a few facts here.

  1. She has an ENS (probably is into crypto stuff)
  2. Has listed a few projects she is affiliated with (could chat about this)
  3. Has "Digital Marketing Agency" as her work (more talking material)
  4. And finally, a link to her (nf.td)

Let's click her nf.td β€” maybe there's more information we need.

Generally, Twitter or other socials are a good place to start. From there, you can click and look at their websites and take a more in-depth look.

Ah! Great. We now have some more clarity about what she is currently working on. And what's this?

She writes!?!? Amazing – that is a gold mine of information.

Look for blogs, websites, and anything that they've created...

and put some interesting facts on your mindmap

Read their posts -> reflect on how this person sees the world.

What interests them? What do they care about?
my early mindmap

Now – try to find common ground

It won't be any good to come to the conversation simply talking about things the other person likes. Find something you both can nerd out on. And make note of that.

For example, after reading Alyssa's article on "Zen", I write out the top 3-4 learnings/questions that I have – I can then include those in our conversation. I will also mark that on my mind map.

Be conscious of time...

Maybe the call is virtual, or maybe it's in person. I find it helpful (in either case) to prepare more than the time that you have available – that way if the conversation goes by a lot faster than it should – or even better – they decide they want to talk longer, you won't run out of material.

Also, have a direction

Any conversation should have a frame.

If you're meeting this person for the first time, ask yourself the question:

"Why do I want to meet his person? What am I curious about?"

The answer to that will serve as the overall framework for the conversation.

Gain a big-picture understanding -> then go small

So the purpose of the mindmap is to create a skeleton of what this person is all about. What are the big categories that characterize what this person is interested in? But! It's also about finding potential overlaps and avenues for conversation.

Continuing our example...

shared interest

So! In this instance, we can see that we're both interested in ~3 things. And that's more than enough to have a conversation.

Prioritize & Pick The Most Engaging Conversation Topic

Once you're clear on what both parties are interested in. Pick the most interesting one. The most exciting one. The one that people could talk about in an intense fervour for hours.

Have the others in your back pocket – conversations often don't go the way you planned them.

Feel Free To Mix & Mash Topics Too

So, if I wanted to come up with a really great topic to speak to Alyssa about – maybe I mash 2 topics together:


So maybe I want to talk to her about "wellness in crypto". If that feels like a really interesting avenue to follow – then do it. Otherwise, stick to just one or two interests.

Build A Flow (Fill in the details)

You won't be able to plan for all contingencies when having conversations. You'll have to think on your feet.

But we can build a bit of a "map" of how we're hoping to direct the conversation.
equal parts art, science, and improv

Conversations at the end of the day are equal parts art, science, and improv. You probably won't get it right the first time but with time – and practice – you will become great.

Convert your mind map to a flow...

I haven't filled it out yet but I am now building out the structure of the convo

Overall Structure Of A Great Conversation

There are 3 main parts of a conversation.

  1. Rapport building (trust building)
  2. Conversating having
  3. Clean up

Rapport Building:

The first 2 minutes of a call/conversation are CRUCIAL. This is where the other person decides to what degree they trust you. Are they comfortable opening up to you? Can they be vulnerable?

Always, always, always. Have a smile on your face. Come with high energy. And make them feel like you're truly pleased to see them (you should be pleased to see them).

It's here where you can have a bit of small talk... Asking them how they are doing. How their day has been thus far? Make introductions.

Your task here is to gauge their energy level, their level of enthusiasm but also whether or not they're paying attention to you (maybe something else is on their mind).

Conversation Having:

This is the bulk of the time spent. Here you're going to co-create a conversation with the other person about whatever topic you have planned.

The goal is to find flow – a rhythm. Where there are equal parts of listening and speaking happening at both ends.

Often times, you'll be doing more listening than talking and that's okay!

This is also where lots of learning can happen, make sure you pay complete attention. Absorb what they're saying, lend your full attention to the story they are trying to tell you.

Clean up:

If the conversation goes well. And things are wrapping up (running up against time constraints or otherwise) – make the ask to join their network.

Pick something context-appropriate. Maybe ask to be their connection on X site or see if they would be open to scheduling a follow-up call sometime in the future.

This all rests on whether or not the other person had a great time speaking with you. Sometimes, if things go well, you might get a request for a follow-up call without even asking!

And make sure you ACTUALLY follow up.

I like to post a summary on Social Media highlighting what we spoke about and tagging them in it.

Putting This Into Practice

So let's flesh out our structure a bit more...

further breakdown

So – I fill in the details here. What exactly do I want to talk about? What would they like to talk about?

And voila! Your conversation guide is complete! You're not memorizing a script here, just creating a strong frame. Something to rely on, something you know will interest both of you.

Conversation Techniques To Use:

I really love the book "Stop asking questions" by Andrew Warner. We'll look into some of the techniques that he shares, that I really like.

Use these techniques while in conversation with others.

Stop Asking Questions

Don't ask questions. Lead.

Rephrase questions to directives.

From "How did you get your first customer?" to "Tell me how you got your first customer."

The other person will appreciate someone taking leadership. And they'll respect you more for it.

Don't Ask "Most" Questions

They suck. And put people on the spot.

Who was the MOST helpful person in your life?

Is a question that forces people to step back, rank people and come back with an answer. Not fun. Breaks flow.

Instead, give people options.

From "Who is the most important person you've hired?" to "Who's an important person you've hired?"

Get Stories...

Stories can be incredibly effective. But it's tough to get them out of people.

You can't just say "can you tell me a story about that?" – it's an awkward request.

Instead, you can ask:

  • Tell me about a time when you did that
  • Do you have an example of that?
  • Take me to the moment that you did X. What did you say?

If they say "I like to celebrate my wins & failures" you can follow up by asking "Tell me about a time that you celebrated a failure."

You get the point.

Get Guarded People To Open Up

Some people will give you resistance. Don't fight it. Join it.

Therapists use this technique to get their patients to open up.

They would say things along the lines of

"Wow, everything seems to be going well for you. It's nice for me to get to talk to someone who has an easy life, who has it good."

That'll open someone right up. But use this technique with incredible care. This is can be seen as manipulation – so ensure you're coming from the right place when you ask.

Listen For "Shoved Facts"

A "shoved fact" is very similar to a Freudian slip. It's something that someone says without knowing it.

So, while speaking with someone about, let's say cars, you might hear them bring up the fact that they're going through a divorce. They might also add that their ex-spouse took their favourite car.

Out of all the things this person could've said, they shoved their divorce into the conversation.

That may be a signal that this is a topic that someone is more interested in speaking about.


Conversations can sometimes feel one-sided. As conversationalists, we must seek to strike a balance between sharing information about ourselves and getting information from others.

Don't get me wrong, others will LOVE to speak about themselves for hours, but afterwards, they might feel like they've been taken advantage of. Like we've sucked information out of them and given nothing in return.

Include a revealing sentence every once in a while. Then let them go back to talking.

Share your why...

This technique is better suited for interview-type conversations but you want to ask people what you want to know directly and why you want to know it.

Andrew gives the following example:

He asked a guest... "Tell me about a time you were depressed." and "Let me see that you're human, not just some guy who's a beaming Tony Robbins."

or another example:

Where an employee is trying to leave his job and is speaking with his boss. His boss is trying to persuade him otherwise. So the employee asks "What's your motivation?" (direct ask) and quickly follows up with "I'm asking because I've always wanted to be an entrepreneur. If I don't do this now, I may never." (the why)

Directly ask – and then make sure to tell them why you're asking.


Because is beautiful.

When you use it, it acknowledges that you have heard what the other has just said and you want to get deeper into the reason why.

It's a great transition if someone is telling you WHAT they're doing but you want to get at the WHY.

"We recently had to re-brand – it took a long time."


"Well, we felt like our old brand wasn't connecting.... blah blah"

Lowball Them

People aren't taught to brag. So this is a way to get humble people to really open up about their achievements.

So imagine that you want to learn about how much someone's business is making per year or something that people don't readily share.

Throw a lowball.

"So, are you making at least a million per year?"

"No! We're making at least 20-30x times that"

Make it absurdly low and they can't HELP but clear the air.

Put Words In Someone Else's Mouth

If you want to ask TOUGH questions. Bring in an imaginary 3rd party and ask the questions from their perspective.

You want to avoid any questions that can come off as an attack.

You can ask things like:

  • What would you say to someone who thought [enter tough question]
  • I imagine someone listening to us thinking [enter tough question] What would you say to that?

This way you still maintain that rapport while still asking tough questions.

Use Double-Barreled Questions

How to ask questions you shouldn't ask.

A double-barreled question is a question that addresses 2 different issues in 1.

You ask an easy question and a hard question in one. We want them to answer the easy one.

Example: You want to ask if someone has divorced their wife. As it was a shoved fact that they mentioned previously.

I might ask: Do you feel comfortable saying if you divorced your wife?

I ask 2 questions there:

  1. Are you divorced?
  2. Do you feel comfortable talking about it?

If they don't feel comfortable, they can take the easy way out and say they aren't comfortable.

Sorry to interrupt...

Sometimes the person you're talking with will go off the rails.

In that case, use the "I'm sorry to interrupt, but..."


  • Sorry to interrupt, but I really want to get into the details of x.
  • I'm sorry to interrupt, but [you said] "x". How do you do x?

Take this moment to interrupt. And share WHY you're interrupting.

Home Run Questions

End on a high note!

Leverage the "peak-end" rule. Humans tend to remember 2 things from an experience. The peak(most intense) and the end.

So ask questions that make them feel good about themselves. They should be easy to answer.

Never end on a tough question.

Off you go! Have Amazing Conversations.

Take this structure that I've given you.

Do some prestudy -> create a mindmap -> find similarities -> create a flow -> build rapport -> use the conversation techniques -> end on a high note Β -> followup

with love,

come on now.