20 Questions

Questions to Ask Mentor About Career Development Reddit

Strategic questions to engage with mentors and gain valuable career development insights, based on popular Reddit discussions and proven mentorship practices.

1

What was your biggest career mistake and what did you learn from it?

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Why this works

Reveals their vulnerability and shows what they learned from failures, providing valuable lessons about resilience and growth from setbacks.

2

How did you identify your career passion and what advice do you have for finding mine?

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Why this works

Shows their self-discovery process and reveals their methods for identifying what truly motivates and fulfills them professionally.

3

What skills do you wish you had developed earlier in your career?

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Why this works

Reveals skill gaps they discovered and shows what additional preparation would have been helpful for their career advancement.

4

How do you handle career transitions and what strategies work best?

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Why this works

Shows their approach to career development and reveals their strategies for navigating career changes and transitions successfully.

5

What is your approach to networking and building professional relationships?

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Why this works

Reveals their networking strategies and shows their methods for building and maintaining valuable professional connections over time.

6

How do you stay current with industry trends and what resources do you recommend?

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Why this works

Shows their commitment to continuous learning and reveals their methods for staying informed about industry developments and trends.

7

What is your approach to work-life balance and how do you maintain it?

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Why this works

Reveals their strategies for managing career and personal commitments and shows their approach to maintaining well-being while advancing professionally.

8

How do you handle different leadership styles and what is your approach to managing up?

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Why this works

Shows their interpersonal skills and reveals their strategies for working effectively with different types of leaders and managers.

9

What is your approach to taking calculated risks in your career?

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Why this works

Reveals their risk assessment skills and shows their methods for evaluating and taking career risks that can lead to growth and advancement.

10

How do you handle failure and what is your approach to bouncing back?

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Why this works

Shows their resilience and reveals their strategies for recovering from setbacks and using failures as learning opportunities.

11

What is your approach to mentoring others and how do you give back?

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Why this works

Reveals their mentorship philosophy and shows their commitment to helping others grow and develop professionally.

12

How do you handle different workplace cultures and what is your approach to adapting?

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Why this works

Shows their adaptability and reveals their strategies for navigating different organizational cultures and environments effectively.

13

What is your approach to salary negotiations and what advice do you have?

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Why this works

Reveals their negotiation skills and shows their strategies for advocating for fair compensation and career advancement.

14

How do you handle different personality types in the workplace?

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Why this works

Shows their interpersonal skills and reveals their strategies for working effectively with diverse personalities and communication styles.

15

What is your approach to building a personal brand and professional reputation?

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Why this works

Reveals their personal branding strategies and shows their methods for building and maintaining a strong professional reputation.

16

How do you handle different learning styles and what is your approach to continuous learning?

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Why this works

Shows their learning strategies and reveals their methods for acquiring new skills and knowledge throughout their career.

17

What is your approach to handling difficult conversations and conflicts?

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Why this works

Reveals their communication skills and shows their strategies for addressing challenging situations and maintaining professional relationships.

18

How do you handle different career stages and what advice do you have for each?

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Why this works

Shows their understanding of career development and reveals their guidance for navigating different stages of professional growth.

19

What is your approach to giving and receiving feedback?

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Why this works

Reveals their communication skills and shows their strategies for providing and accepting constructive feedback for professional growth.

20

What advice would you give to someone just starting their career in your field?

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Why this works

Shows their mentorship approach and reveals the guidance they would offer to someone beginning their professional journey.

Best Practices for Mentor Career Development Conversations

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

Best Practices

Be Specific About Your Goals

Clearly articulate your career goals and challenges. This helps mentors provide more targeted and relevant advice for your specific situation.

Show Genuine Interest

Listen actively and ask follow-up questions that demonstrate your interest in their experiences and advice. This builds stronger mentor relationships.

Take Action on Advice

Follow through on the advice you receive and report back on your progress. This shows respect for their time and helps them see the impact of their guidance.

Question Sequences

The Experience and Learning Sequence

1
What was your biggest career mistake and what did you learn from it?
2
What skills do you wish you had developed earlier?
3
How do you handle failure and what is your approach to bouncing back?
4
What is your approach to continuous learning?

The Skills and Development Sequence

1
How do you identify your career passion?
2
What is your approach to networking and building relationships?
3
How do you handle different leadership styles?
4
What is your approach to building a personal brand?

Common Pitfalls

Don't Ask for Job Opportunities Too Early

Focus on learning and building relationships first. Don't immediately ask for job opportunities or favors from your mentor.

Don't Ignore Their Time

Be respectful of their time and don't overstay your welcome. Keep conversations focused and efficient.

Don't Make Assumptions

Avoid making assumptions about their experiences or career path. Ask questions to understand their specific journey and advice.

Conversation Templates

The Experience and Learning Focus

1
Step 1: Start with: "What was your biggest career mistake and what did you learn from it?"
2
Step 2: Follow with: "What skills do you wish you had developed earlier?"
3
Step 3: Explore with: "How do you handle failure and what is your approach to bouncing back?"
4
Step 4: Conclude with: "What is your approach to continuous learning?"

The Skills and Development Focus

1
Step 1: Begin with: "How do you identify your career passion?"
2
Step 2: Investigate with: "What is your approach to networking and building relationships?"
3
Step 3: Explore with: "How do you handle different leadership styles?"
4
Step 4: Clarify with: "What is your approach to building a personal brand?"

Further Reading

"The Complete Guide to Career Mentoring" by National Association of Colleges and Employers
"Mentorship Best Practices" by Society for Human Resource Management
"The Mentor's Handbook" by American Management Association

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