- Going Places by Janel Abrahami
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- Coffee Chat to Job Offer?
Coffee Chat to Job Offer?
How to turn Informational Interviews into actual opportunities

How to Turn Coffee Chats into Career Opportunities: A Strategic Guide
Let's talk about something we all know but hate to admit: landing amazing opportunities - whether it's your dream 9-5 role, freelance clients, or side hustle partnerships - often comes down to who you know. In fact, about 70% of dream opportunities never make it to job boards or public platforms. They go to people who've mastered the art of strategic networking.
But here's the thing: whether you're hunting for a full-time gig or building your empire as a freelancer, you're probably making the same networking mistakes. (Don't worry, we've all been there!)
π€¦ The Common Mistakes (Yes, We've All Made Them!)
Raise your hand if this sounds familiar: You're doing all the "right" things - reaching out for coffee chats, asking about career paths, and ending every conversation with some version of "please keep me in mind for opportunities!"
Been there, done that, got the lukewarm coffee to prove it.
Here's why these well-intentioned efforts often fall flat:
You're so worried about coming across as "salesy" that you hide your valuable skills
You stick to safe, Google-able questions instead of having organic conversations
You leave with nothing but a caffeine buzz and vague promises to "stay in touch"

π‘ The Mindset Shift: From Coffee Date to Strategy Session
Here's the game-changer: stop thinking of these as casual chats where you're asking for favors.
Instead, think of them as strategic conversations where you're exploring how your superpowers could solve their headaches.
This works whether you're:
Job hunting for that perfect full-time role
Looking for freelance clients
Building partnerships for your side hustle
Exploring fractional opportunities
Because guess what? Everyone has problems that need solving - and that's where you come in!
β Your Pre-Chat Homework (I Promise It's Worth It!)
Instead of falling down the company history rabbit hole, focus on things that actually matter:
What's new and exciting (or challenging) in their world?
Any recent changes that might spell opportunity?
Industry trends that could be keeping them up at night?
Pro tip: If you're exploring fractional or freelance opportunities, pay extra attention to projects or initiatives that might need external support!
π Questions That Make You Stand Out (And Actually Lead Somewhere)
Forget "So, how did you get into this field?" (Snooze!) Try these conversation starters instead:
For The Problem Detectives:
"What's the biggest challenge your team is facing right now?"
"I noticed [recent company news] - how's that shaking things up in your world?"
"What's got you most excited (or worried) about next quarter?"
For The Opportunity Hunters:
"What does a rockstar look like in this kind of role?"
"What's that one problem you wish you had more help solving?"
"Where do you see the biggest opportunities for someone with my background to add value?"
π The Art of the Value Preview (Without Being Pushy!)
When they mention a challenge that's in your wheelhouse, it's showtime! Here's how to casually flex your problem-solving muscles:
"Oh, that's interesting - I actually tackled something similar..."
Share a quick win story
Offer to share the BTS on how you did it
For example: "That social media struggle sounds familiar! I actually helped a client boost their engagement by 60% using a super simple content strategy. Happy to share what worked if you're interested!"
π€ Closing Like a Pro (No Awkward Goodbyes!)
Instead of the vague "let's stay in touch," try these natural next steps:
If They're Facing Specific Challenges:
"I've got some ideas about that [problem they mentioned]. Want to schedule a follow-up chat to dive deeper?"
If They're Growing:
"Sounds like you'll be scaling up soon! Mind if I share some thoughts on how I might be able to help with that?"
If There's No Immediate Fit:
"I'd love to connect with others on your team who might be wrestling with similar challenges. Anyone come to mind?"
βͺοΈ The Follow-Up That Actually Works
Within 24 hours, send them a note that shows you were listening and adds value:
Reference something specific you discussed
Share a helpful resource or idea
Mention next steps you both agreed on

The Bottom Line
Whether you're looking for a full-time role, freelance gigs, or side hustle opportunities, the secret sauce is the same: be the solution to someone's problems. Focus on understanding and solving their challenges, and the opportunities will follow - no awkward networking required!
Remember: Everyone you meet is potentially dealing with a problem you're perfectly suited to solve. Your job is just to help them figure that out! π
KGYGT (keep going, you got this),
Janel
Thank you to Rippling for supporting this issue!
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