20 Questions

Questions to Ask When Job Shadowing

Thoughtful questions to maximize your job shadowing experience, understand daily responsibilities, career paths, and what it really takes to succeed.

1

Can you walk me through what a typical day looks like in this role?

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Why this works

Establishes realistic expectations about workflow and time allocation.

2

What brought you to this career, and how did you get started?

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Why this works

Reveals pathways into the field and motivations.

3

What's the most rewarding part of your job?

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Why this works

Highlights what keeps them engaged and passionate.

4

What's the most challenging or stressful aspect of this work?

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Why this works

Surfaces realities that aren't visible from the outside.

5

What skills are most important for success in this role?

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Why this works

Helps you identify gaps and prioritize learning.

6

What does a successful outcome look like in your work?

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Why this works

Clarifies how performance is measured and what matters most.

7

How much of your time is spent on [specific task] versus other responsibilities?

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Why this works

Breaks down the role into concrete activities.

8

What's something you wish you'd known before entering this field?

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Why this works

Offers insider perspective and lessons learned.

9

How has this role or industry changed since you started?

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Why this works

Shows trends and whether the field is evolving or stagnant.

10

What does work-life balance look like in this position?

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Why this works

Assesses sustainability and whether the job fits your lifestyle goals.

11

What opportunities for advancement or growth exist in this field?

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Why this works

Reveals whether there's a clear career path or ceiling.

12

How do you continue learning and staying current in your field?

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Why this works

Shows whether continuous education is expected and how it's pursued.

13

What's the team or organizational culture like here?

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Why this works

Provides context on whether the environment is supportive or toxic.

14

How much autonomy do you have in your work, and how are decisions made?

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Why this works

Clarifies whether the role offers independence or is highly structured.

15

What tools, technologies, or systems do you use daily?

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Why this works

Identifies technical skills you may need to develop.

16

How do you handle unexpected problems or crises?

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Why this works

Shows problem-solving processes and whether the work is reactive or proactive.

17

What advice would you give to someone starting out in this field?

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Why this works

Surfaces practical wisdom and common pitfalls to avoid.

18

Are there any misconceptions people have about this job?

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Why this works

Corrects unrealistic expectations and glamorized views.

19

What does the hiring process look like, and what do employers look for?

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Why this works

Prepares you for job applications and interviews.

20

Is there anything else I should know or any other questions I should ask?

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Why this works

Invites them to share insights you may not have thought to request.

Maximizing Your Job Shadow

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

Before You Shadow

1
Research the role, organization, and industry beforehand.
2
Prepare questions in advance but stay flexible to ask follow-ups.
3
Dress appropriately for the workplace culture.
4
Bring a notebook and pen to take notes throughout the day.

During the Shadow

Observe not just tasks but also interactions, pace, and environment.
Ask questions at appropriate times—don't interrupt critical work.
Be respectful of their time and energy.
Take notes on what surprises you or differs from your expectations.

After the Shadow

1
Send a thank-you note expressing appreciation and what you learned.
2
Reflect on whether the role aligns with your interests and goals.
3
Follow up if they offered to stay in touch or provide resources.
4
Update your career plan based on new insights gained.

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