The Coffee Chat

How to complete The Coffee Chat

This is an informational interview: a low-stakes conversation with someone already doing the work you want, aimed at learning the unwritten path rather than asking for a job. The real value is in closing the loop afterward, so the person sees their advice mattered.

1. Pick someone roughly 2-5 years ahead of you, not a CEO so senior the gap is useless
2. Send a short, specific ask: reference their work, request 20-25 minutes, propose coffee or a video call
3. Prepare 4-5 real questions about their path, mistakes, and what they'd do differently, not questions Google can answer
4. Listen more than you talk; take notes and ask one concrete follow-up before you leave
5. Within a week, act on one piece of their advice, then email them what you did and the result

Tips

• Never pitch yourself for a role in the first chat; it kills the goodwill
• Keep it to the time you asked for, and end early if they seem busy
• A thank-you that names a specific thing they said beats a generic one

What counts as done

You held the conversation and sent a follow-up describing a real action you took on their advice.