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280: How I turn strangers into authentic connections

4 min

Here's something career advice rarely addresses: the follow-up after meeting someone interesting. We all know to connect on LinkedIn, but then what? It feels awkward to reach out later, so we just... don't. I'll share how to turn those brief encounters into meaningful relationships.

Here’s one for all single people out there:

A long time ago, in a Youtube vid far away, a dating coach was talking about people waiting on meeting their “true love”, and said:

(Paraphrasing)

“Most of you have probably already met the love of your life, but you didn’t go up and talk to them. You missed your chance. And even worse: you could bump into the love of your life tomorrow, and you still wouldn’t know what to do!”

Now, I’m not a dating coach….

But I think that’s a very, very good point when it comes to networking in our careers.

We’re waiting for a magical “connection” to change everything…

But if said magical person sat down at our conference table… or got in our elevator or taxi cab, would we know what to do about it?

If the answer’s “no”, here’s a few things that might help:

What you CAN’T do

Please, please, please don’t do this:

You meet someone, add them on LinkedIn, never talk to them, and then 3 years later, you pop out of the woodwork looking for a favour. 

People don’t like that. It’s cold. And shows a lack of basic understanding of how relationships work.

To use a finance analogy, you’re making withdrawals without putting anything in.

But, what should you do?

Start with….

🔂 The charmed follow-up

Talking of true love, when I was in high school, I sneezed in class, and a girl said, “Bless you” out loud, in front of the whole class.

I’ve never forgotten that (evidenced by me writing about it all these years later 😂)

Why?

Because it was kind, considerate, but also, highly unusual. 

Who says, “Bless you” in public anymore?

I mention it because this is what a good follow-up should do too: be kind, considerate, totally charming, and quite unexpected.

An easy way to do this?

Fire them an email with a genuine compliment:

✅ “Hey Susan, just wanted to drop a note saying it was fantastic meeting you the other day.

I loved our convo about living in Madrid. I’m still smiling away at your Prado story. Hilarious. I’ll definitely have to visit someday.

Let’s grab churros & chocolate sometime,

Kay

Ok, next step:

🌟 Write down their “spark”

If the other person was truly memorable, it’ll be easy to remember their one, burning passion (their “spark”) - whether that’s woodwork, wasabi or Warhammer 40k. But often, time passes, and you forget.

So…

Write it down.

(In a notebook, excel file, wherever). 

And then…

🎁 Send them their spark!

I heard a story one time about this entrepreneur who, when he meets someone, he gets his secretary to send them a gift based on their spark.

So the story goes…

One time, he bumps into a billionaire. (As you do). And it turns out, the billionaire loves Ferraris. (As billionaires do). 

So, the entrepreneur’s secretary sends him a stunning coffee-table book about Ferraris, with a note saying, “Thought you might like this.”

Result?

Our entrepreneur gets a phone call a few days later. 

It’s the billionaire. 

“That book!” he raves. “It was so good. Listen: what can I do for you?”

Now…

You don’t need to send physical gifts. (Although there’s nothing stopping you). And sometimes it’ll be impossible, because you don’t have their address. 

So an approach I’d recommend instead is:

👑 The Content King (or Queen)

My sister’s friend is a master at this.

He’s a voracious reader, and when he stumbles across something online that he knows someone in his network would love, he sends it their way with a small note, “idk if relevant, but thought i'd share!". 

This takes him zero time (he’s reading anyway), but delivers a lot of value to his connections.

Do something similar. 

As you’re reading, watching videos, or listening to podcasts, think "who would find this interesting?" Then forward it on, saying:

✅ "Thought you might enjoy this!”

Or..

"Saw this and remembered our convo about Y"

Just remember:

My sister’s friend doesn’t expect a reply, and neither should you.  And although he sometimes doesn’t get one, you can bet your boots the kind gesture registers in the other person’s brain.

🌐 Use LinkedIn (properly)

Here's the thing about staying in touch: it's hard to do with everyone.

But that's where LinkedIn becomes your best friend.

Add people after you meet them. Then, use the platform to stay visible - without the heavy lifting of one-on-one catch-ups.

(one more tip: avoid cringey dramatic linkedin influencer type of posts — sharing funny stuff is cool and shows you have personality!)

One post = reaching hundreds of connections at once.

Also, here’s a harsh truth: People maintain relationships with interesting people.

If you're regularly sharing good (and fun!) stuff, people will WANT to stay connected with you. They'll remember you exist. They'll reach out to catch up. And when you reach out more personally, it won’t feel as out of the blue.

(Btw, make sure you optimize your LinkedIn profile first — so you nail your online impression and you look like someone with authority in your industry. Use our free tool here to help — it’s by far the best thing out there when it comes to anything LinkedIn optimization)

My point: Don't just collect connections. Use LinkedIn to stay interesting, stay visible, and keep those relationships warm - at scale.

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