The Ultimate Conversation Cheat Sheet: What to Ask Your Mentor

Okay, so you’ve walked into the Mentorship Lounge (or logged onto the app). You’ve sat down across from a mentor. You’ve said "Hi."

...Now what?

If your brain just went blank, don't panic. It happens to the best of us. Sometimes the hardest part isn't wanting to know something, it's knowing how to ask it.

To help you out, we’ve created the Ultimate Conversation Cheat Sheet. Think of this like a menu. You don't have to ask every single question. Just pick 2 or 3 that sound interesting to you.

Remember: This isn't an interview. It’s just a chat.

Part 1: The Icebreakers (How to Start)

If you don't know how to begin, try one of these instead of just "What do you do?"

• "What is the coolest project you’ve ever worked on?"

• "What was your very first job? Did you like it?"

• "If you weren't working in tech, what would you be doing instead?"

• "What’s the one app on your phone you can’t live without?"

Part 2: Confidence & "Real Talk" (Soft Skills)

These questions are great for "Soulful Mentorship." They help you learn how to handle stress, fear, and growing up.

• "I get really nervous when I have to speak in public. Did you ever feel that way? How did you get over it?"

• "Have you ever failed at something big? How did you bounce back?"

• "I sometimes feel like I’m not smart enough for tech (Imposter Syndrome). Do adults ever feel that way?"

• "What is the best piece of life advice someone ever gave you?"

• "How do you balance working hard with actually having a life/hobbies?"

Part 3: The Future & School (College Readiness)

Stressing about SATs, majors, or which college to pick? Ask someone who has already survived it.

• "I don't know what I want to major in yet. Is that okay?"

• "Does the name of the college I go to actually matter in the tech world?"

• "I’m thinking about community college or a gap year. What do you think about non-traditional paths?"

• "What is one class you took in school that you actually use in your job today?"

• "If you could go back and tell your High School self one thing, what would it be?"

Part 4: The Job Hunt (Careers in Tech)

Tech isn't just coding. Use these questions to find out what jobs are actually out there.

• "I’m not great at Math/Coding. Is there still a place for me in tech?" (Hint: The answer is YES).

• "What does a 'day in the life' actually look like for you?"

• "What are some jobs in tech that nobody talks about but are really cool?"

• "I’m interested in [Art/Music/Fashion]. How can I combine that with technology?"

• "What skills are more important: technical skills (like coding) or people skills (like teamwork)?"

Part 5: Wrapping It Up

When you’re ready to go, here is how to end the conversation like a pro.

• "This was really helpful, thank you for your time."

• "Do you have a LinkedIn or an email where I could stay in touch?"

• "Is there a book or a podcast you recommend I check out?"

One Last Tip: There is no such thing as a "stupid question." If you are curious about it, ask it. Your mentor is here to help you unlock your future, one question at a time.