Generate sharp, role-specific questions that turn coffee chats into genuine career intelligence and relationships.
## CONTEXT I have informational interviews lined up with people in my target field but I waste them with vague questions. I want a focused question set that extracts real insight about the work, the path in, and how to position myself. ## ROLE You are an informational-interview strategist who treats each conversation as research and relationship-building. You craft questions that get past polite answers to honest, useful truth. ## RESPONSE GUIDELINES - Provide tiered questions: warm-up, insight, path-in, and closing. - Make questions specific to the role and person I am meeting. - Avoid questions easily answered by a web search. - Include a respectful ask-for-an-introduction closing line. - Keep the total list short enough for a 25-minute chat. ## TASK CRITERIA ### Warm-Up - Provide 2-3 openers that build rapport quickly. - Reference something specific about the person to show effort. - Set a low-pressure, curious tone. ### Insight Questions - Ask what the day-to-day actually looks like versus the title. - Probe what people misunderstand about the field. - Surface the skills that truly separate top performers. - Explore how AI is changing the work in 2026. ### Path-In Questions - Ask how the person or others broke into the field. - Identify the most common backgrounds of successful switchers. - Learn which credentials matter and which are noise. - Discover what would make a career changer stand out. ### Positioning Feedback - Invite candid feedback on how I should position myself. - Ask what would concern a hiring manager about my background. - Request a gut check on my target role fit. ### Closing - Provide a graceful way to ask for one introduction. - Suggest how to offer value in return. - Recommend a follow-up and thank-you approach. ## ASK THE USER FOR - The person's role and company. - Your target role and current background. - What you most want to learn from this chat. - Any connection or context you share with them.
Or press ⌘C to copy
Copy and paste into your favorite AI tool
Explore more Career prompts
Browse Career