Before picking questions, get clear on your actual question. Are you deciding whether a role fits your day-to-day preferences? Trying to understand an industry before committing months to a pivot? Trying to figure out how someone actually got into a role you want? Each of those points to a different set of questions -- pick 4-6, not 20, and let the conversation breathe rather than running through a checklist.

Use these when you're trying to understand whether the day-to-day matches the job description.

- Walk me through what a typical Tuesday looks like in this role. - What surprised you most about the job after you started? - What do you spend more time on than you expected? Less? - What's the hardest part of the job that doesn't show up in the posting? - What would you tell someone considering this move who isn't sure yet?

Use these when you're deciding between companies or industries, or trying to understand the landscape before you apply.

- How would you describe the culture on your team in three words? - What's changing most in the industry right now? - How do decisions actually get made on your team? - What does success look like in this role six months in?

**Career-path questions:** - How did you get here -- a straight path or a series of pivots? - If you were doing it over, what would you do differently? - What skills or experiences mattered most for your first break in this field?

**'Who else should I talk to' questions:** - Who else should I be talking to as I figure this out? - Are there communities, newsletters, or events you'd recommend? - If you were me, what's the one next step you'd take this week?