2 days ago I was at the Starbucks in Sofia airport.

the girl behind the counter notices my tattoos. I notice hers.

I say something about it. she says "it's a recent one. but I'm not sure about it."

so I tried something I learned this week from an FBI hostage negotiator.

I repeated her last 3 words.

"not sure about it?"

she paused. then kept going.

"I got it on a bad day. a friend offered to make it. it looks nice but I still don't know what meaning I want to give it."

"it's a set of keys. they could unlock new perspectives in my life. or cool new things. maybe I'm just waiting for something good to happen."

we talked for 15 minutes. I barely said a word. she told me about her life, her hopes, her doubts. all because I repeated three words and waited.

her name was Sveti. I never would have heard any of this if I'd been talking about myself.

Why am I doing this?

earlier this week I contacted 1,500 leaders. CEOs, founders, coaches. cold emails and calls. one question: what's the skill that changed your life?

the majority said listening.

not sales. not confidence. not networking. listening.

so I checked my own numbers. my Zoom recordings. my calls.

I talk 70% of the time.

that means in a 10-minute conversation, the other person gets 3 minutes. that's bad. Im sorry Im doing this to you friend.

so the week 10 challenge: fix this. I gave myself one week to learn how to actually listen.

120 questions later, here's what I learned

I spent this week asking questions. to strangers, friends, people in coworking spaces, baristas, anyone who'd talk to me. around 120 conversations in total.

most of them taught me the same 2 things.

lesson 1: the 5-second pause

this is the simplest technique I've ever tested. and it changed every single conversation.

when someone finishes talking, don't respond immediately. count to 5 in your head. just wait.

here's what happens.

most people aren't actually done when they stop talking. they pause to see if you'll jump in. if you don't, they keep going. and the second thing they say is almost always more honest, more interesting, and more real than the first.

I tested this over and over. someone would finish a sentence. I'd wait. and they'd add something they weren't planning to say. the real story. the thing underneath the thing.

five seconds of silence told me more than five minutes of clever questions.

I'm a terrible listener. I interrupt. I relate everything back to myself. but those five seconds gave the other person room to actually exist in the conversation.

try it today. just once. someone finishes talking. count to five. see what they say next.

lesson 2: most conversations die because of bad questions

"how are you?" "fine."

"what do you do?" "marketing."

"how's your weekend?" "good."

dead. every time.

people are not boring. the problem is we ask boring questions. questions that can be answered in one word. questions that don't require any thought or vulnerability.

I spent this week testing different questions. and the ones that actually opened people up all had something in common: they asked about feelings, not facts.

"what are you excited about right now?" works. "what do you do?" doesn't.

"what's been on your mind lately?" works. "how are you?" doesn't.

"what's something you changed your mind about recently?" gets people to stop and actually think. "how was your day?" gets you "fine."

so I'm building something for you.

100 questions to create real connection.

questions that make conversations actually interesting. questions that get people talking about what matters instead of what's safe. organized by situation: strangers, friends, dates, work, deep conversations.

I'm putting it together based on everything I tested this week. the ones that worked, the ones that flopped, and the ones that surprised me.

Free, in this simple Google Doc, click HERE to check it.

what I didn't expect

I went into this week thinking listening was passive. a soft skill. something nice people do.

it's not.

the 5-second pause made strangers trust me faster, asking better questions gave me access to stories and perspectives I would have missed entirely.

It allowed me to connect authentically with people so I believe it's an extremely valuable skill.

It can profoundly impact your life when you know how to consciously do it, how to listen with intention.

next week: the thing that scares people more than death!

week 11: public speaking. on a real stage.

I’ll be at the Italy Nomad Fest in Palermo.

hundreds of people. a microphone. me.

We will learn this together.

see you monday from Palermo.

ps: reply to this email and tell me: what's one question you wish people asked you more often? I might add it to the 100 questions list.

Proof:

If you missed the previous weeks and unusual lessons, check them out HERE:

Reply to this email with all your questions, comments, or tips, I will answer.

Or share with friends who want to join and grow.

- Alex