20 Questions

Questions to Ask a College Graduate

Thoughtful questions to ask recent college graduates about their experiences, lessons learned, and advice for navigating post-graduation life.

1

What's the most valuable lesson you learned in college, inside or outside the classroom?

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Why this works

Reveals what had lasting impact beyond academics and what truly shaped their development.

2

If you could go back to your freshman year, what advice would you give yourself?

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Why this works

Uncovers regrets, missed opportunities, and wisdom gained through experience.

3

What class or professor had the biggest impact on you, and why?

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Why this works

Identifies transformative educational experiences and influential mentors.

4

How did you choose your major, and would you choose it again?

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Why this works

Provides insight into decision-making and whether they feel satisfied with their academic path.

5

What surprised you most about college life?

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Why this works

Reveals unexpected challenges or discoveries that shaped their college experience.

6

What skills do you wish you had developed more during college?

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Why this works

Highlights gaps they now recognize and practical skills they value in retrospect.

7

How did you balance academics, social life, and personal well-being?

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Why this works

Offers practical strategies for managing the competing demands of college life.

8

What was your biggest challenge in college, and how did you overcome it?

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Why this works

Demonstrates resilience and problem-solving approaches that led to growth.

9

What do you miss most about college now that you've graduated?

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Why this works

Reveals what aspects of college life they found most valuable or enjoyable.

10

How are you feeling about entering the 'real world' after graduation?

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Why this works

Opens conversation about post-graduation anxiety, excitement, and transition challenges.

11

What's your plan for the next year—job, travel, grad school, or something else?

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Why this works

Provides insight into their immediate goals and how they're navigating the transition.

12

What internship or work experience was most valuable during college?

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Why this works

Highlights practical experiences that prepared them for their career.

13

How did you build your professional network during college?

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Why this works

Offers strategies for connecting with mentors, peers, and industry professionals.

14

What extracurricular activities or clubs were most meaningful to you?

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Why this works

Reveals how they developed leadership, found community, and explored interests.

15

What's one thing you wish you had known before starting college?

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Why this works

Provides advice for prospective students based on their lived experience.

16

How did college change you as a person?

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Why this works

Explores personal growth, identity development, and transformation during college years.

17

What was the best decision you made during your college years?

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Why this works

Identifies pivotal choices that positively shaped their experience or trajectory.

18

How did you manage student loans or financial concerns?

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Why this works

Provides practical financial advice for handling college costs and debt.

19

What advice would you give to someone starting college or about to graduate?

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Why this works

Synthesizes their wisdom into actionable guidance for others at different stages.

20

Looking back, what are you most proud of accomplishing in college?

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Why this works

Celebrates their achievements and reveals what they value most about their college experience.

Best Practices for Learning from College Graduates

Expert tips and techniques for getting the most out of these questions.

Best Practices

Ask Open-Ended Questions

Let them tell their story rather than seeking yes/no answers. Their narrative contains valuable context.

Listen for Patterns

If multiple graduates mention the same advice or regrets, pay attention—those insights are especially valuable.

Don't Just Focus on Success

Ask about challenges and failures too. These often contain the most valuable lessons.

Follow Up with Specifics

When they mention something important, dig deeper with 'Can you tell me more about that?' to get actionable details.

Conversation Sequences

The Reflection Sequence

1
What's the most valuable lesson you learned in college?
2
If you could go back to your freshman year, what advice would you give yourself?
3
What do you miss most about college now that you've graduated?

The Practical Advice Sequence

1
What skills do you wish you had developed more during college?
2
How did you balance academics, social life, and personal well-being?
3
What's one thing you wish you had known before starting college?

The Career Preparation Sequence

1
What internship or work experience was most valuable during college?
2
How did you build your professional network during college?
3
What's your plan for the next year after graduation?

Common Pitfalls

Don't Assume Their Path Is Universal

Every college experience is unique. What worked for them may not apply to everyone.

Don't Make Them Defensive About Choices

Avoid questioning their major or decisions in ways that imply judgment.

Don't Only Ask About Grades and Jobs

Personal growth, relationships, and life skills are just as important as academic or career success.

Don't Pressure Them to Have Everything Figured Out

Recent graduates often feel uncertain. Don't add to that pressure with expectations of perfect clarity.

Conversation Templates

The Informational Interview Framework

1
Step 1: Start with: 'Congratulations on graduating! What's the most valuable lesson you learned?'
2
Step 2: Follow with: 'What advice would you give someone starting college?'
3
Step 3: Deepen with: 'What do you wish you had done differently?'
4
Step 4: Close with: 'Thank you for sharing. Your insights are really helpful'

The Mentorship Request

1
Step 1: Start with: 'I'd love to learn from your experience. Can I ask you a few questions?'
2
Step 2: Follow with: 'What was your biggest challenge in college, and how did you overcome it?'
3
Step 3: Ask: 'How did you figure out your post-graduation plans?'
4
Step 4: Close with: 'Would you be open to staying in touch as I navigate college?'

Further Reading

"Designing Your Life" by Bill Burnett and Dave Evans
"The Defining Decade" by Meg Jay
"Range" by David Epstein

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