Why Starting Networking Conversations Feels Hard (and How to Fix It)
The Simple Conversation Trick That Makes Networking Easy
Welcome to issue #172 of The Introverted Networker. Every Tuesday, I teach you to be a better networker. My favorite part of the week is hearing from my readers, so leave a comment or ask a question, if you are so inclined.
There’s one thing I keep hearing from readers:
“I don’t know how to start networking conversations.”
Not how to keep them going.
Not how to follow up.
Just how to begin.
If that’s where you get stuck, you’re not alone, and you’re not doing anything wrong.
Here’s how to fix it!
This issue takes about 5 minutes to read…
Starting conversations feels awkward for almost everyone.
But here’s the mindset shift most people never use:
Put yourself in their shoes.
If you only take one thing from this newsletter, let it be this.
Because when you see the interaction through their eyes instead of yours, most of the fear disappears.
Let’s walk through exactly how to start conversations, online and in real life, and how this simple mindset shift makes it so much easier.
Starting Conversations Online (The Easiest Doorway)
People usually overthink online outreach because they imagine they’re imposing.
“Am I bothering them?”
“Do I sound needy?”
“Do they think I want something?”
But put yourself in their shoes:
If a former coworker messaged you today and said,
“Hey, it’s been a while. How have you been?”
…you wouldn’t be annoyed.
You’d probably smile.
You’d feel remembered.
Most people would.
The shift to “how would I feel if they messaged me first?” removes 90% of the awkwardness.
That’s why reaching out to people you already know, but haven’t talked to in awhile is such a low-stress way to start.
These are people who already know your name.
You’re not interrupting their day; you’re reconnecting.
Simple Re-connection Messages
Use any of these:
“Hey, it’s been a while. How have things been going?”
“You came to mind this week and I realized we haven’t talked in forever. What’s new with you?”
“I saw something that reminded me of you and wanted to check in. How are things?”
Short. Friendly. No agenda.
Exactly the kind of message you would appreciate receiving.
After They Reply
This is where overthinking sneaks back in unless you use the same mindset shift.
Ask yourself:
“If I were them, what kind of conversation would feel comfortable?”
Usually:
A few simple questions.
A genuine “how have you been?”
A chance to share what’s going on in their world.
Then, once the back-and-forth feels natural:
“Great catching up a bit. Want to jump on a quick call sometime next week?”
Online → real conversation.
This small step is where almost all relationship growth happens.
Why This Works
Because when you put yourself in their shoes, you realize:
People like being remembered.
They aren’t judging your wording; they’re glad you reached out.
A delayed response usually means “busy,” not “annoyed.”
Empathy kills awkwardness.
Starting Conversations in Real Life (Without Feeling Forced)
Starting conversations in person feels harder until you stop focusing on yourself and start focusing on the other person.
Again: put yourself in their shoes.
If someone walked up to you at work and said,
“Hey, how’s your week going?”
…you wouldn’t freeze.
You wouldn’t think it was strange.
You’d probably appreciate the human moment.
Most people would.
Use the Context Around You
People always know how to respond when the question fits the setting.
At work:
“How’s your team handling the new project?”
At an event:
“What brought you here today?”
At a conference:
“Learn anything interesting this morning?”
If the roles were reversed, these would feel like easy questions to answer.
So ask them.
Curiosity Over Impressiveness
You don’t have to be interesting.
You just have to be interested.
Ask questions you would enjoy being asked:
“What’s something you’re working on that’s been interesting lately?”
“What’s one challenge your team is wrestling with right now?”
“What’s been helping you most at work these days?”
You’re making the conversation comfortable for them, and in return, it becomes comfortable for you.
Use Empathy to Guide What You Actually Do
Putting yourself in their shoes doesn’t just help your mindset.
It tells you exactly what action to take.
Give First (AIR: Advice, Introductions, Recommendations)
If you would want someone to lead with helpfulness, do the same.
Giving kills the fear of “taking advantage.”
Be Easy to Help
When they eventually ask,
“How can I help you?”
don’t hand them a heavy lift.
If you were helping someone, you’d want a clear path too.
So instead of:
“Can you take my résumé to your recruiter?”
Try:
“I’m exploring these 6 companies. If you know anyone there, I’d love an introduction.”
That’s simple.
Respectful.
Easy.
Exactly how you would want to be asked.
These are approaches I share in my online course, “5 Steps To Grow Your Professional Network.” this is where I teach you the process I use everyday to grow my professional network.
The Real Goal: Move From Moment → Relationship
Starting the conversation is not the win.
The win is what you build after.
A simple path:
Message or small talk.
Quick call or coffee.
A short follow-up.
Give something helpful.
Add them to your keep-in-touch list.
A handful of conversations like this each month grows a strong network without events, without small-talk anxiety, and without pretending to be someone you’re not.
Your 10-Minute Challenge This Week
Do one of these small things:
Send one re-connection message to a person you have lost touch with.
Start one in-person conversation with someone at work you don’t know well.
If both of you switched roles, you’d appreciate it.
That’s the quiet truth behind all of this.
One small action.
One simple conversation.
One moment where you treat someone the way you’d want to be treated.
That’s how networking becomes natural and how connection starts to grow.
The Introverted Networker Extras:
As always, I have lots more networking advice on The Introverted Networker YouTube channel.
Best Things I Found Online This Week:
Jenny Wood shared a great follow-up script for networking conversations.
If you want to ask better questions in your networking conversations, Greater Good Science Center has a list of 36 questions for increasing closeness. Pick one and try it this week.
The challenge many have with starting up a conversation is that they are worried about what might go wrong.
It’s making people too hesitant to try.
I find that people who are open to taking will always make it easy for you even if you say the wrong thing, so I try to walk up to people and make a random observation:
“I wish they made more of these sandwiches.”
If they respond, great. If not, I walk away!