20 Questions

Questions to Ask During a Job Shadow

Strategic questions to maximize job shadowing experiences, understand career realities, and gather insights beyond what's visible in daily observation.

1

What does a typical day look like in this role?

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Why this works

Provides baseline understanding of routine, variety, and normal workflow patterns.

2

What do you enjoy most about your job?

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Why this works

Reveals positive aspects, intrinsic rewards, and what makes the role satisfying long-term.

3

What are the most challenging aspects of this work?

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Why this works

Shows realistic difficulties, stress factors, and problems you'll face in this career.

4

How did you get into this career, and what path did you take?

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Why this works

Indicates various entry routes, educational requirements, and how people actually break into field.

5

What skills are most important for succeeding in this role?

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Why this works

Shows both technical and soft skills that matter most in actual work versus job descriptions.

6

How much of your time is spent on different types of tasks?

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Why this works

Reveals true time allocation between appealing work and less glamorous necessities.

7

What surprised you most when you started this job?

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Why this works

Uncovers gap between expectations and reality that newcomers commonly experience.

8

How has this role changed since you started?

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Why this works

Shows career evolution, industry trends, and whether field is growing or contracting.

9

What opportunities exist for advancement or specialization?

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Why this works

Indicates career trajectory possibilities, growth potential, and long-term prospects.

10

How do you balance work and personal life in this career?

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Why this works

Provides honest perspective on lifestyle, hours, and whether sustainability is realistic.

11

What education or training is required, and what was most valuable?

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Why this works

Shows necessary credentials versus what actually prepared them for real work.

12

How collaborative is this work versus independent?

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Why this works

Reveals team dynamics, autonomy level, and whether you'll work alone or with others.

13

What do you wish you had known before entering this career?

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Why this works

Provides insider wisdom, avoided mistakes, and realistic expectations setting.

14

How do you handle stress or difficult situations in this role?

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Why this works

Shows coping mechanisms, pressure management, and emotional demands of position.

15

What are the salary expectations and compensation structure for this field?

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Why this works

Indicates realistic earning potential, benefits, and financial viability of career path.

16

How do you continue learning and developing in your career?

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Why this works

Shows ongoing education needs, professional development expectations, and growth requirements.

17

What personality traits or work styles fit well with this job?

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Why this works

Reveals whether your temperament matches role demands and what types succeed.

18

What's something about this job that outsiders wouldn't understand?

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Why this works

Uncovers insider perspective, hidden realities, and nuances not visible from outside.

19

How has technology changed how you do your work?

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Why this works

Shows industry evolution, tool requirements, and whether field is adapting or disrupting.

20

If you could do it over, would you choose this career again?

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Why this works

Ultimate satisfaction indicator revealing whether rewards outweigh challenges.

How to Use These Questions

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

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