FREE Question Bank for Career Coffee Chats

Not sure what to ask in an informational interview — or worried about sounding awkward?

This question bank removes that stress and sets you up for a powerful chat!

Inside, you’ll find 30+ smart, natural questions you can use to lead confident, meaningful conversations. The questions are organized by theme, so you can quickly choose what fits your goals, the person you’re speaking with, or the flow of the conversation.

You’ll find questions that help you:

• Understand someone’s career path and decision points

• Get real insight into roles, skills, and day-to-day work

• Learn about industry trends, opportunities, and risks

• Explore company culture and hiring processes

• Ask for advice, recommendations, and next connections (without it feeling forced)

You don’t need to ask every question. This is a pick-and-choose tool designed to support genuine curiosity and confident conversations — not scripted interviews.

Best for: students, new grads, career changers, and job seekers exploring the hidden job market.

👉 If you want more guidance on Informational Interviews - including email templates, preparation, structuring your time, follow-up, and how to turn conversations into real momentum, check out the full Beyond Resumes: Informational Interview Toolkit.