The quality of an informational interview depends almost entirely on the quality of the questions asked — generic questions produce generic answers, while specific and informed questions produce insight worth having. AI can help generate a set of questions calibrated to the person's role, background, and industry that signal genuine preparation. This concept covers what makes an informational interview question worth asking.
Informational interview question generation is the preparation technique of crafting thoughtful, specific questions to ask industry professionals during networking conversations — questions that demonstrate genuine research, uncover insider knowledge, and build memorable rapport rather than wasting someone's time with questions Google could answer. The quality of your questions determines the quality of the intelligence you gather and the impression you leave.
AI can generate a customized question set based on a specific person's background, company, and role in minutes, making every informational interview feel like a prepared, strategic conversation rather than an awkward cold call.
Copy a contact's LinkedIn profile and their company's About page, then paste both into ChatGPT with the prompt: 'I have a 20-minute informational interview with this person. Generate 10 thoughtful questions that show I've researched their background and company, focus on their career path and day-to-day reality, and would help me understand whether this role and industry are right for me. Avoid anything easily answered by their LinkedIn profile.'
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