A great coffee chat is mostly listening. These are the questions I come back to because they consistently lead somewhere interesting:
1. How did you get to where you are today? Everyone’s path is different, and the detours are usually the most instructive part.
2. What does a typical week actually look like? Job titles hide a lot. The day-to-day tells you whether a role is a fit.
3. What skills matter most that people overlook? The answer is often communication, judgment, or relationships, not just technical skill.
4. What do you wish you had known earlier in your career? This is where the best advice usually comes from.
5. Is there anyone else you think I should talk to? One good conversation often leads to the next. I always follow up with a thank-you and let them know how the introduction went.