20 Questions

Questions to Ask a Mentor About Career Development

Essential questions to ask a mentor about career development to gain insights, guidance, and advice for advancing your professional journey.

1

What's your career journey been like and what key decisions shaped it?

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Why this works

Helps you understand their path and gives you insights into the decisions and experiences that led to their success.

2

What are the most important skills I should develop for career success?

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Why this works

Reveals the skills they value most and helps you understand what competencies to focus on for professional growth.

3

What's your advice for building a strong professional network?

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Why this works

Shows their networking approach and helps you understand how to build and maintain valuable professional relationships.

4

How do you approach career planning and what's your strategy?

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Why this works

Reveals their career planning methodology and helps you understand how to develop a strategic approach to your career.

5

What are the biggest mistakes you've seen people make in their careers?

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Why this works

Shows the pitfalls to avoid and helps you understand what not to do, which is just as important as knowing what to do.

6

How do you handle career setbacks and what's your approach?

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Why this works

Reveals their resilience strategy and helps you understand how to navigate challenges and bounce back from setbacks.

7

What's your view on the role of mentorship in career development?

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Why this works

Shows their perspective on mentorship and helps you understand how to leverage mentoring relationships for career growth.

8

How do you approach learning and professional development?

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Why this works

Reveals their learning strategy and helps you understand how to continuously develop your skills and knowledge.

9

What's your advice for finding and pursuing career opportunities?

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Why this works

Shows their opportunity-seeking approach and helps you understand how to identify and pursue career opportunities.

10

How do you balance career ambitions with personal life?

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Why this works

Reveals their work-life balance approach and helps you understand how to maintain harmony between career and personal goals.

11

What's your perspective on the role of failure in career development?

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Why this works

Shows their view on failure and helps you understand how to learn from setbacks and use them for growth.

12

How do you approach building credibility and reputation in your field?

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Why this works

Reveals their reputation-building strategy and helps you understand how to establish yourself as a credible professional.

13

What's your advice for transitioning between different career paths?

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Why this works

Shows their transition approach and helps you understand how to navigate career changes and new opportunities.

14

How do you approach working with different types of people and what's your strategy?

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Why this works

Reveals their people management approach and helps you understand how to work effectively with diverse personalities.

15

What's your view on the role of technology in career development?

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Why this works

Shows their perspective on technology and helps you understand how to leverage digital tools for career advancement.

16

How do you approach building and maintaining professional relationships?

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Why this works

Reveals their relationship-building strategy and helps you understand how to cultivate meaningful professional connections.

17

What's your advice for developing leadership skills and what's your approach?

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Why this works

Shows their leadership development strategy and helps you understand how to build and demonstrate leadership capabilities.

18

How do you approach working with different generations and what's your experience?

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Why this works

Shows their generational awareness and helps you understand how to work effectively with different age groups.

19

What's your perspective on the role of purpose and values in career development?

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Why this works

Shows their approach to purpose-driven career development and helps you understand how to align your career with your values.

20

What's the most important thing I should know about career development?

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Why this works

Gives them a chance to share what they think is most important for you to know, providing valuable insights about career development.

Best Practices for Career Development Mentoring

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

Best Practices

Show Genuine Interest

Demonstrate genuine curiosity about their career journey and advice. Ask thoughtful questions that show you're engaged and interested.

Be Respectful of Their Time

Be mindful of their schedule and responsibilities. Ask if they have time to talk and be concise in your questions.

Ask Follow-up Questions

Show engagement by asking follow-up questions that build on their answers. This demonstrates active listening and deeper interest.

Question Sequences

The Career Journey Sequence

1
What's your career journey been like?
2
What are the most important skills I should develop?
3
What's your advice for building a strong network?

The Development Strategy Sequence

1
How do you approach career planning?
2
What's your advice for finding opportunities?
3
How do you approach learning and development?

Common Pitfalls

Don't Make Assumptions

Avoid assuming you know their approach or perspective. Ask questions to understand their specific methods and insights.

Don't Be Overly Critical

While healthy skepticism is good, avoid being overly critical or dismissive of their advice. Show respect for their experience.

Don't Focus Only on Controversial Topics

While important topics are worth discussing, don't make every conversation about controversial or divisive subjects.

Conversation Templates

The Career Journey Exploration

1
Step 1: Start with: "What's your career journey been like?"
2
Step 2: Follow with: "What are the most important skills I should develop?"
3
Step 3: Conclude with: "What's your advice for building a strong network?"

The Development Strategy

1
Step 1: Begin with: "How do you approach career planning?"
2
Step 2: Explore with: "What's your advice for finding opportunities?"
3
Step 3: Finalize with: "How do you approach learning and development?"

Further Reading

"The First 90 Days" by Michael Watkins
"Crucial Conversations" by Kerry Patterson
Career development and mentoring resources

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