At CareerOS, one of the tools we strongly believe in when it comes to building authentic, career-shaping relationships is the coffee chat. Whether you’re exploring a new field, trying to break into a specific company, or simply learning from someone a few steps ahead — these casual, 20-minute conversations can open doors that job boards never will.

But we get it — reaching out to someone you don’t know and asking for their time? It can feel awkward or even intimidating. That’s why we’ve put together this ultimate guide to help you approach coffee chats with confidence — packed with scripts, prep tips, and ways to keep the relationship going long after the call ends.

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Step 1: Who Should I Even Ask?

You don’t need to go straight to the CEO. In fact, it’s often better not to. Here’s who to target:

  • Someone in a role you’re curious about
  • Someone who made a career move you’re considering
  • Alumni from your school or program
  • People who seem active or approachable on LinkedIn
  • Friends-of-friends you can ask for a warm intro

🎯 CareerOS Tip: Start with people who are 1–3 years ahead of you. They remember what it’s like to be in your shoes — and they’re often the most willing to help.

Step 2: How to Ask for a Chat

Reaching out doesn’t have to be scary. The key? Keep it short, kind, and clear. Here’s a message you can copy, paste, and tweak:

Hi [Name],
I came across your profile while exploring [industry/role] and really admired your journey from [X to Y]. I’d love to learn more about your experience at [Company] and hear any advice you might have for someone just starting out. Would you be open to a 20-minute chat sometime soon?

Keep it under 100 words
Send via LinkedIn or email
Follow up once if you don’t hear back — it’s not pushy, it’s professional

❗What if they don’t reply?

Totally normal. It doesn’t mean you did anything wrong.

People get busy, miss messages, or simply don’t have the capacity to say yes — and that’s okay. Don’t take it personally. You’re putting yourself out there, and that alone is a win.

Keep going. For every 5 messages you send, you might get 1–2 replies — and that’s more than enough to start building real connections.

Pro Tip: Keep track of all your networking activity using the Contacts page on CareerOS. Track your follow-ups, and don’t be afraid to cast a wide net. Coffee chats are a numbers game — and one “yes” can make a big difference.

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Step 3: Prep Smart

A little prep = a lot more confidence. And more importantly — it shows.

When you come in with thoughtful questions and clear curiosity, the person on the other end can feel it. You're showing them that you genuinely care, that you respect their time, and that you're not just ticking a “networking” box.

Remember: they’re taking time out of a busy day to speak with you — the least you can do is make it a great experience for them too.

Here’s how to prep:

✅ Read their LinkedIn profile — take note of anything unique about their journey, career pivots, or posts you can reference
✅ Know what their company does — you don’t need to be an expert, but at least skim their website or recent news
✅ Prepare your 30-second “about me” — just a quick intro with who you are, what you’re exploring, and why you reached out
✅ Jot down 5–6 meaningful questions — focus on what you genuinely want to learn from them, not what you think you should ask
✅ Set up your space — quiet, good lighting, and camera-ready if it’s a virtual chat (first impressions count!)

🎯 CareerOS Insight: The best coffee chats feel like a conversation — not an interview. But behind every relaxed, natural chat is someone who came prepared.

Make it easy for them to say, “Wow, this person really showed up — I’m glad I took this call.”

That’s how you build lasting relationships.

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Step 4: During the Chat — What to Say & Ask

Alright, you’ve done the prep. Now it’s game time — but don’t stress. A great coffee chat isn’t about being perfectly polished; it’s about being curious, thoughtful, and respectful.

Remember: this isn’t an interview. You don’t need to prove yourself. You’re here to learn, listen, and build a real connection.

🗣 Start with your intro

“Thanks so much for making time today! I’m [Name], currently [studying/working at X], and I’m exploring opportunities in [field]. I really appreciate you being open to chatting — I’ve been looking forward to learning more about your experience.”

💡 Why it matters: A warm, clear intro sets the tone. You're showing respect, sharing your context, and inviting them into a conversation—not just asking them to talk at you.

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What to Ask: Go Beyond the Basics

This is your chance to learn things you can’t Google. Focus on personal insights, lived experiences, and the human side of their journey.

Questions to Ask:

Their journey

  • How did you get into this line of work?
  • Were there any turning points that shaped your path?

Their day-to-day

  • What does your typical day look like?
  • What do you love most about your work?
  • What’s one challenge you didn’t expect in this role?

Their company

  • What’s the team culture like?
  • What kind of people thrive at [Company]?

Advice for you

  • What would you focus on if you were starting out today?
  • Any resources, platforms, or people you recommend connecting with?

Next steps

  • Is there anyone else you’d recommend I speak with?

And always respect their time:

“I want to be mindful of your time—just one last question if that’s okay…”

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Step 5: Follow Up & Keep the Relationship Going

Right after:

Send a thank-you message. Keep it personal and specific:

“Thank you again for the chat today! I really appreciated your advice about [X] and the insight into [Y]. I’ll definitely look into [resource/tip] and keep you posted. Hope we can stay in touch!”

Over time:

  • Connect on LinkedIn
  • Comment on their content
  • Send occasional updates when something meaningful happens (e.g. an interview, new job, or resource you tried based on their advice)

TL;DR: Your Coffee Chat Game Plan

  1. Pick someone relevant to your goals
  2. Send a short, sincere message
  3. Prep your intro + 5 solid questions
  4. Keep the convo friendly, curious, and concise
  5. Follow up with gratitude — and stay connected

Here at CareerOS, we believe that career growth isn’t just about applying to jobs — it’s about building relationships. Coffee chats are one of the simplest (and most powerful) ways to do that. So go ahead. Reach out. Start the conversation. You might be one message away from your next opportunity.

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