Tailored Questions for Students, Grads, and Career Paths

Once you've covered the basics, it can be helpful to dive into questions tailored to your background, goals, or area of study. Whether you're a student or recent grad, the prompts below are designed to help you make your conversations more relevant and actionable. Pick the ones that speak to your situation and use them to get deeper insights from your mentor.

General

How did you figure out what you wanted to do after university/college?
If you were in my shoes, what would you be doing to explore options?
What’s something you wish you did earlier in your career journey?
What entry-level roles should I be looking at if I’m still unsure?
What helped you stand out for your first full-time role?
How would you approach a job search today as a new grad?
What advice do you have for someone without internship experience yet?
Would you be open to reviewing my resume or LinkedIn?
- What stands out or could be improved?
How should I showcase projects, clubs, or side hustles?
Can I try out my elevator pitch and get your feedback?
How do you approach the “Tell me about yourself” question?
What’s your best advice for staying calm and confident in interviews?
What's the hardest interview you've done, why was it difficult, what was the outcome? Do you wish you would have done something different?
What's something that has surprised you about your job?
What is the work/life balance like?
How do you keep yourself organized and what's your approach to prioritization?

Business Majors

What roles do business grads usually start in at your company?
How would you explore career options if you’re not sure whether to go into marketing, finance, HR, or operations?
What made you pick your current role coming out of business school?
Are there business functions I should consider that aren’t as obvious or well-known?
Is getting an MBA something you’ve considered or would recommend down the line?

Sales

What’s the best way to break into sales without sales experience?
What do hiring managers in sales look for beyond a good GPA?
How do you stay motivated through rejection or slow periods?
How important are soft skills like storytelling and confidence?
What’s your advice for building strong client or customer relationships early on?

STEM (Science, Tech, Engineering, Math)

How did you translate your academic work into industry experience?
How do employers in tech or science assess entry-level talent?
Should I be learning extra tools or programming languages outside of class?
Are research experiences or labs seen as valuable in industry hiring?
What’s your advice for working on cross-functional teams as a new grad?

Marketing & Advertising

What helped you get into your first agency or brand-side role?
How can I be building a portfolio or personal brand even as a student?
How would you suggest I stand out if I’m applying to creative roles?
What are the differences between agency vs. in-house work?
What are underrated roles in marketing or advertising that I should know about?
Who do you think is doing good work and why?

Communication, Confidence, and Leadership

What communication habits have helped you stand out most in your career?
How do you approach explaining complex ideas to different audiences?
What’s one thing I can do to come across as more confident in meetings or interviews?
What makes someone great to work with, from your perspective?
How do you build trust quickly when working with a new team?
What have you seen early-career professionals do that strengthens (or hurts) their relationships with colleagues/leadership?
How can someone early in their career show leadership without being in a formal leadership role?
What small actions signal that someone is ready for more responsibility?
How do you influence decisions when you’re not the most senior person in the room?

About the Company and/or Industry?

What do you enjoy most about working at [Company]?
What’s the company culture really like day-to-day?
What skills or traits seem to help people succeed here?
How does the company support growth or career mobility?
What do you think makes someone stand out early on at [Company]?
What trends do you see shaping the industry right now?
Where do you think the biggest opportunities will be over the next few years?
What challenges do newcomers often face in this industry?
What surprised you most when you first started in this field?
What advice would you give someone trying to break in?

Questions for Mentors Who Work With (But Aren’t In) Your Desired Role

How do you work with [desired role]?
From where you sit, what traits or skills do you notice the most in people who succeed in [desired role]?
What do people in [desired role] do really well that makes them stand out at your company?
Where do you see most people in that role fall short
Are there habits or approaches you’ve noticed that separate the good from the great in that position?
From your perspective, how does [desired role] collaborate with other teams, and what makes those partnerships effective?
Are there projects, skills, or experiences outside the role itself that give someone an edge when applying for it?

Not sure where to start or looking for broader questions? Check out Questions to Make the Most of Your Mentor Meetup for general conversation starters that work in any session. Using both sets together can help you feel more confident, prepared, and ready to get the most out of every meetup.

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