some housekeeping before the rest of the letter:
toronto folks. i’ll be at a networking event this week with some amazing people i recently did a workshop with. they’ve opened it to the public, so if you want to come meet me (and grab a free drink with your tix), snag a slot here
until the end of may, i’m reviewing brand and content strategy on tiktok... for free.
follow me here, then send me a dm saying you’re from the newsletter. i’ll add you to a private list where you can watch the strategy breakdowns i’m making, or i’ll review your content directly. whichever you want.
now back to the letter..
i wasn’t always good with people.
like... genuinely not good. shy, quiet, the kind of person who would rather send a message than make a phone call. i’d walk into a room full of strangers and immediately look for the corner.
and to be honest, i have never felt like I’ve become a pro at this. but i know a couple things are key in how i’ve managed to become more and more of a true community member.
i wrote a newsletter a few weeks ago about why the people who reply are the whole point. a lot of you responded to that one. and the thing you kept asking was: okay, but how? how do you actually get good at this?
so this one is the how.
i spent the last week writing this and pulling this together. it wasn’t easy lmao so hopefully it’s helpful to someone.
30 things i’ve learned about connecting with people. not theory. not stuff i read in a book. just what’s actually worked for me, organized by where and when you’d use it. you might agree or disagree with some, but these have been key to who i am now and everything i do now.
let’s get into it.
here’s a letter to younger me
1. mindset shifts: how you think about people before you even open your mouth
this is where it starts. before the room, before the conversation, before any of it. the way you think about people determines everything that comes after.
1. remember everyone is just a person. they’ve all been a child. they’ve all been confused, embarrassed, unsure. nobody was born important. the person across from you is figuring it out too.
2. most people are just as nervous as you are. you’re not the only one hoping it goes well. that person who looks so confident? they walked in with the same quiet anxiety you did. you’re not alone in this.
3. you don’t have to please everyone. some people will fall off. that’s not a failure on your part. that’s filtering. the ones who are supposed to stay, stay.
4. be true to who you are. this sounds obvious until you’re in the room twisting yourself into someone you’re not because you think it’ll land better. it won’t. people feel authenticity. they feel the absence of it too.
5. the right people find you in every universe. i really believe this. if you’re real, if you’re genuinely yourself, the people who are meant to be in your life will keep showing up. in different rooms, different cities, different chapters. they find you.
6. stop waiting until you feel “ready” to connect. there’s no ready. you already have enough to offer. the version of you that exists right now is worth knowing.
2. online: building real connection in digital spaces
most people use the internet to broadcast. the people person uses it to actually connect. small difference. massive results.
7. when someone posts a birthday story, swipe up right then. not later. not “i’ll do it when i finish scrolling.” right then. it takes five seconds and it genuinely makes people feel seen. most people walk past it. don’t be most people.
8. when someone comes to mind, send it immediately. you’re watching a show and something reminds you of your friend? send it. you see a tweet that’s literally them? send it. don’t save it for later. later never comes. the impulse is the signal.
9. leave comments, not just likes. a like is a nod from across the room. a comment is actually walking over. it takes thirty seconds and it can make someone’s whole day. it can spark a conversation you never saw coming. and it works for people you know and people you’ve never met.
10. reply to people’s posts instead of just sharing them. showing up in someone’s mentions hits different than sharing their content. anyone can share. not everyone takes the time to actually respond.
11. when a comment goes deep, move the conversation. if you and someone are going back and forth in the comments and it’s actually getting interesting... slide into the DMs. move it somewhere more personal. that’s how online becomes real.
12. follow people intentionally. actually read what they post. engage with it. don’t follow someone just to grow your own numbers and then never look at their content. that’s not connection, that’s collecting.
3. with strangers: meeting new people, first impressions, breaking ice
strangers are just people you haven’t connected with yet
13. lead with a genuine compliment. something you actually noticed. not “nice shoes” because you couldn’t think of anything else. something specific. something real. people can feel the difference instantly.
14. be genuinely curious. ask about something specific you saw or heard. not a generic “so what do you do?” but something that shows you were actually paying attention to them.
15. don’t ask about things you don’t care about. seriously. if you’re not actually curious, don’t fake it. it shows on your face. in your eyes. in the way you’re already thinking about the next thing to say. genuine curiosity opens people up. the absence of it closes them down just as fast.
16. ask “what are you working on right now?” instead of “what do you do?” “what do you do?” gets you a job title. “what are you working on?” gets you a story. always go for the story.
17. use their name once early in the conversation. not in a weird, over-the-top way. just naturally, once. it signals that you actually heard them when they introduced themselves. it’s a small thing. it lands every time.
18. let silences breathe. not every gap needs to be filled. a comfortable pause isn’t awkward. it’s actually a sign that you’re both present enough to just... be in the moment. let it exist.
4. in the room: how you show up when you’re actually somewhere with people
being in the room is one thing. actually being present in the room is something else.
19. smile when someone enters. be the first one to do it. before they’ve earned it, before you know if you’ll like them, before anything. just smile. it’s disarming in the best way.
20. match people’s energy. if someone is low, meet them where they are. don’t bring the hype to someone who’s clearly going through something. if someone is high and excited, rise with them. reading the room isn’t a soft skill. it’s everything.
21. don’t be overbearing with your story. when it’s time to introduce yourself, go all in. tell your story. but don’t force it on people who didn’t ask. the most magnetic people in the room are usually the ones asking the best questions, not telling the biggest stories.
22. put your phone away. all the way away. not face down on the table. away. when someone is talking to you, they should have all of you. that’s rare now. that’s exactly why it matters.
23. pay attention to who’s on the edges. the person standing alone at the edge of the room is usually the most interesting one there. the loudest voice in the center isn’t always the most valuable. go find the edges.
24. ask follow-up questions. “and then what happened?” is one of the most powerful things you can say to another person. it tells them you were actually listening. it tells them their story matters. use it.
5. staying connected: keeping the relationship warm after
meeting someone is just the beginning. what you do after is where the relationship actually lives.
25. when someone crosses your mind, that’s the signal. reach out right then. not tomorrow. not when you have something to say. right then. “hey, you randomly came to mind. hope you’re doing well.” that’s it. that’s enough.
26. check in with no agenda. “thinking of you, hope you’re good” is a complete message. you don’t need a reason. you don’t need to want something. just checking in because you care is one of the most underrated things you can do for a relationship.
27. celebrate their wins publicly. comment on the announcement. share the thing. show up when it counts. private congratulations are nice. public ones mean something different.
28. remember the small things. if they mentioned something last time you spoke, bring it up next time. “how did that interview go?” “did you end up taking that trip?” remembering the small things is the most powerful relationship move there is. people don’t forget that.
29. follow up within 24-48 hours of meeting someone new. the energy is still fresh. the conversation is still warm. don’t let it go cold. a quick message within two days is the difference between someone becoming part of your world and just... someone you once met.
30. schedule connection time like you schedule work. left to chance, it won’t happen. your calendar fills up. life takes over. block time for it the same way you block time for a meeting. it sounds overly structured. it works.
that’s 30.
pick one. just one. try it this week.
and if one of these hit different for you, or if you have one i missed, reply and let me know. i read every single one.
mike
which one are you starting with?