20 Questions

Questions to Ask at a Job Shadow

Strategic questions that help you make the most of your job shadow experience while demonstrating your interest in the field and gathering valuable career insights.

1

What does a typical day look like in this role?

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Why this works

Provides insight into daily responsibilities and helps you understand the practical aspects of the position and work environment.

2

What skills and qualifications are most important for success in this field?

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Why this works

Reveals the key competencies needed and helps you understand what skills to develop for career success in this area.

3

How did you get started in this career and what path led you here?

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Why this works

Provides valuable career guidance and reveals the educational and professional journey that led to their current position.

4

What do you enjoy most about your work and what keeps you motivated?

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Why this works

Reveals the rewarding aspects of the career and shows what motivates professionals in this field to stay engaged and satisfied.

5

What are the biggest challenges you face in this role?

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Why this works

Shows understanding of the realities of the job and reveals the difficulties and obstacles professionals encounter in this field.

6

What opportunities exist for career advancement and professional growth?

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Why this works

Reveals career progression opportunities and shows the potential for advancement and development within the field.

7

How has this industry or field changed since you started your career?

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Why this works

Provides insight into industry trends and evolution while showing how the field has developed over time.

8

What advice would you give to someone considering this career path?

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Why this works

Provides valuable career guidance and reveals practical advice for those interested in pursuing this career.

9

What educational background or training is most valuable for this field?

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Why this works

Reveals educational requirements and shows what academic preparation is most important for success in this career.

10

How do you stay current with industry trends and developments?

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Why this works

Shows interest in continuous learning and reveals how professionals in this field keep up with industry changes and developments.

11

What networking opportunities exist in this field?

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Why this works

Reveals professional networking opportunities and shows how to build relationships and connections within the industry.

12

What work-life balance challenges do you face in this role?

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Why this works

Shows understanding of work-life balance and reveals the challenges professionals face in maintaining personal and professional balance.

13

How do you handle stress and pressure in this position?

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Why this works

Reveals coping strategies and shows how professionals manage the demands and pressures of their work.

14

What technology or tools are most important for success in this field?

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Why this works

Shows interest in practical skills and reveals the technical tools and technologies professionals use in their work.

15

How do you collaborate with colleagues and other departments?

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Why this works

Reveals the collaborative nature of the work and shows how professionals interact and work with others in their organization.

16

What professional development opportunities are available in this field?

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Why this works

Shows interest in continuous growth and reveals available training, certification, and development opportunities.

17

How do you measure success in this role?

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Why this works

Reveals performance expectations and shows how professionals evaluate their success and effectiveness in their work.

18

What ethical considerations or challenges do you face in this field?

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Why this works

Shows understanding of professional ethics and reveals the ethical dilemmas and considerations professionals encounter.

19

How do you handle mistakes or setbacks in your work?

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Why this works

Reveals resilience and problem-solving approaches while showing how professionals learn from and recover from challenges.

20

What would you do differently if you were starting your career over?

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Why this works

Provides valuable career insights and reveals lessons learned and advice for those beginning their career journey.

Best Practices for Job Shadow Conversations

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

Best Practices

Show Genuine Interest in the Field

Demonstrate authentic curiosity about the career, industry, and work. Ask questions that show you're thinking about your future in this field.

Focus on Learning and Development

Ask questions that help you understand how to prepare for and succeed in this career. Show interest in skill development and career growth.

Be Respectful of Their Time

Ask thoughtful, well-timed questions that don't interrupt their work flow. Show appreciation for the opportunity to shadow them.

Question Sequences

The Career Path and Development Sequence

1
How did you get started in this career?
2
What skills are most important for success?
3
What educational background is most valuable?
4
What advice would you give to someone considering this career?

The Daily Work and Challenges Sequence

1
What does a typical day look like?
2
What are the biggest challenges you face?
3
What do you enjoy most about your work?
4
How do you handle stress and pressure?

Common Pitfalls

Don't Ask Too Many Questions at Once

Space out your questions throughout the day rather than overwhelming them with a barrage of questions. Let the conversation flow naturally.

Don't Focus Only on Salary and Benefits

While compensation matters, don't make every question about money. Show interest in the work itself, career development, and professional growth.

Don't Ignore the Learning Opportunity

Remember that job shadowing is primarily a learning experience. Ask questions that help you understand the field and prepare for your future career.

Conversation Templates

The Career Exploration Approach

1
Step 1: Start with: "I'm interested in learning about this career..."
2
Step 2: Ask: "How did you get started in this field?"
3
Step 3: Explore: "What skills are most important for success?"
4
Step 4: Follow up: "What advice would you give to someone considering this career?"

The Daily Work and Challenges Approach

1
Step 1: Begin with: "I want to understand what this work is really like..."
2
Step 2: Ask: "What does a typical day look like?"
3
Step 3: Explore: "What are the biggest challenges you face?"
4
Step 4: Connect: "How do you handle stress and pressure?"

Further Reading

"The Career Playbook" by James M. Citrin
"What Color is Your Parachute?" by Richard N. Bolles
"The 2-Hour Job Search" by Steve Dalton
"Knock 'em Dead" by Martin Yate

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