When it comes to finding your next job or figuring out your next career move, it’s easy to fall into the habit of applying endlessly on job boards. But if there’s one strategy we swear by at CareerOS, it’s the coffee chat — a short, informal conversation that can open doors, build real connections, and give you insights you won’t find online.

Whether you’re exploring a new field, curious about someone’s journey, or trying to break into a specific company, a 20-minute chat with someone in the know can be more valuable than any cover letter you’ve ever written.

Still, we get it — reaching out to someone you don’t know can feel awkward or intimidating. So in this guide, we’re breaking it down step-by-step: how to find the right people, what to say when you reach out, how to prep, what to ask, and how to stay in touch after the conversation.

Step 1: Who Should You Ask for a Coffee Chat?

Here’s the good news: you don’t need to reach out to the top executive at your dream company. In fact, your best conversations often come from people who are just a few steps ahead of you.

Look for:

• Someone in a role you’re genuinely curious about
• A professional who made a career shift similar to the one you’re considering
• Alumni from your school or program
• People who are active (and seem approachable) on LinkedIn
• Friends-of-friends who you can ask for a warm introduction

At CareerOS, we often recommend starting with people who are one to three years ahead of where you are. They still remember what it’s like to be in your shoes and are usually the most open to helping.

Step 2: How to Reach Out (Without the Awkwardness)

Sending that first message can feel nerve-wracking — but it doesn’t have to be. Keep it short, kind, and clear. You’re not asking for a job; you’re simply inviting someone to share their story.

Here’s a message you can tweak and make your own:

Hi [Name],
I came across your profile while exploring [industry or 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 short 20-minute chat sometime soon?

A few tips:

• Keep your message under 100 words
• Send it via LinkedIn or email
• If you don’t hear back, it’s okay to follow up once — politely and professionally

And if they don’t respond? That’s completely normal. People get busy, miss messages, or just don’t have the time. Don’t take it personally. Keep reaching out. Even one or two replies out of five messages is a great start.

To stay organized, CareerOS has a built-in Contacts page where you can track your outreach and follow-ups — no spreadsheet needed.

Step 3: How to Prepare for a Coffee Chat

The best conversations feel natural, but behind every smooth chat is a bit of thoughtful preparation. Taking a few minutes to get ready will boost your confidence — and it shows the other person you respect their time.

Here’s how to prep:

• Take a look at their LinkedIn profile and make note of anything that stands out
• Read up on their company — no need to memorize every detail, just know the basics
• Prepare a short 30-second introduction: who you are, what you’re exploring, and why you reached out
• Write down 5–6 thoughtful questions you’re genuinely curious about
• If it’s a video chat, find a quiet spot with decent lighting and test your setup

A little prep goes a long way. It’s the difference between a generic chat and a memorable conversation.

Step 4: What to Say During the Coffee Chat

Now that you’re prepped, it’s time for the actual conversation. Remember: this isn’t an interview. There’s no pressure to impress. You’re just here to learn, listen, and connect.

Start with a warm, simple introduction:

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

From there, let the conversation flow. Ask questions that go beyond what you could Google. Focus on their real-world experiences and advice they’d give someone starting out.

Here are a few solid questions to guide your chat:

About their journey

• How did you get into this field?
• Were there any moments that really shaped your career path?

About their role

• What does a typical day look like?
• What do you enjoy most — and what’s been unexpectedly challenging?

About their company

• What’s the culture like?
• What kinds of people tend to thrive there?

Advice for you

• If you were starting out again, what would you focus on?
• Are there any people, resources, or communities you’d recommend?

Wrap up by being respectful of their time:

I want to be mindful of your schedule — just one last question if that’s okay.

Step 5: Follow Up and Stay Connected

After the chat, don’t forget to follow up. A simple thank-you message goes a long way — and it helps the conversation continue beyond just one call.

Try something like this:

Thank you again for the chat today. I really appreciated your advice on [insert topic] and your insight into [something specific they shared]. I’ll definitely check out [resource or tip] and keep you posted. Hope we can stay in touch!

From there, make it a point to stay connected:

• Add them on LinkedIn if you haven’t already
• Drop a comment or a like on something they share
• Send a short message every so often if you have an update, like a new job, interview, or something they helped you with

These small touchpoints build real, lasting relationships.

One Chat Could Lead to Big Things

At CareerOS, we’ve seen time and time again how one conversation can lead to an internship, a mentor, or even your dream job. Coffee chats aren’t about getting immediate results — they’re about planting seeds. You’re showing curiosity, initiative, and a genuine desire to learn.

So go ahead — find someone whose story you admire. Reach out. Show up prepared. Say thank you. And keep the conversation going.

You never know where it might lead.

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