Questions to Ask While Job Shadowing
Thoughtful questions to ask during a job shadowing experience to understand daily responsibilities, career paths, challenges, skills needed, and workplace culture—maximizing your learning and career exploration.
1Can you walk me through what a typical day looks like for you?
Click to see why this works
Can you walk me through what a typical day looks like for you?
Click to see why this works
Why this works
Grounds your understanding in real workflows beyond idealized job descriptions.
2What do you enjoy most about your job?
Click to see why this works
What do you enjoy most about your job?
Click to see why this works
Why this works
Reveals intrinsic motivators and what makes the role fulfilling.
3What's the most challenging or frustrating part of your work?
Click to see why this works
What's the most challenging or frustrating part of your work?
Click to see why this works
Why this works
Surfaces realistic downsides and daily struggles you should anticipate.
4What skills do you use most frequently in your role?
Click to see why this works
What skills do you use most frequently in your role?
Click to see why this works
Why this works
Identifies practical competencies to develop if you pursue this path.
5How did you get into this field, and what was your career path?
Click to see why this works
How did you get into this field, and what was your career path?
Click to see why this works
Why this works
Maps potential entry points and trajectories within the profession.
6What education or training was required to get this job?
Click to see why this works
What education or training was required to get this job?
Click to see why this works
Why this works
Clarifies prerequisites and helps you plan your own pathway.
7How much of your time is spent on [specific task I observed] versus other responsibilities?
Click to see why this works
How much of your time is spent on [specific task I observed] versus other responsibilities?
Click to see why this works
Why this works
Quantifies time allocation to understand job composition accurately.
8What's something you wish you'd known before entering this field?
Click to see why this works
What's something you wish you'd known before entering this field?
Click to see why this works
Why this works
Surfaces insider wisdom and realistic expectations.
9How do you manage your workload and prioritize tasks?
Click to see why this works
How do you manage your workload and prioritize tasks?
Click to see why this works
Why this works
Reveals time management strategies and how pros stay organized under pressure.
10What opportunities exist for advancement or specialization in this career?
Click to see why this works
What opportunities exist for advancement or specialization in this career?
Click to see why this works
Why this works
Assesses long-term growth potential and career ceiling.
11How do you stay current with industry trends, tools, or best practices?
Click to see why this works
How do you stay current with industry trends, tools, or best practices?
Click to see why this works
Why this works
Shows commitment required for ongoing learning and professional development.
12What's the work-life balance like in this role?
Click to see why this works
What's the work-life balance like in this role?
Click to see why this works
Why this works
Gets honest perspective on hours, flexibility, and sustainability.
13Can you explain what you're working on right now and why it matters?
Click to see why this works
Can you explain what you're working on right now and why it matters?
Click to see why this works
Why this works
Contextualizes tasks within broader goals and impact.
14How do you collaborate with others in your role?
Click to see why this works
How do you collaborate with others in your role?
Click to see why this works
Why this works
Reveals team dynamics, communication patterns, and interdependencies.
15What personality traits or soft skills are important for success here?
Click to see why this works
What personality traits or soft skills are important for success here?
Click to see why this works
Why this works
Identifies cultural and interpersonal fit factors beyond technical skills.
16What tools, software, or technologies do you use daily?
Click to see why this works
What tools, software, or technologies do you use daily?
Click to see why this works
Why this works
Lists practical tech skills to acquire if pursuing this career.
17How does your company culture affect your day-to-day experience?
Click to see why this works
How does your company culture affect your day-to-day experience?
Click to see why this works
Why this works
Explores how values, norms, and environment shape work satisfaction.
18What advice would you give someone interested in this career?
Click to see why this works
What advice would you give someone interested in this career?
Click to see why this works
Why this works
Opens space for candid guidance tailored to your interest.
19Are there aspects of the job that don't match public perceptions or stereotypes?
Click to see why this works
Are there aspects of the job that don't match public perceptions or stereotypes?
Click to see why this works
Why this works
Corrects misconceptions and reveals hidden realities of the role.
20Is there anything I should observe or ask about that I haven't yet?
Click to see why this works
Is there anything I should observe or ask about that I haven't yet?
Click to see why this works
Why this works
Invites the professional to highlight important aspects you might have missed.
Making the Most of Job Shadowing
Expert tips and techniques for getting the most out of these questions.
Best Practices
Observe First, Ask Later
Watch workflows unfold before interrupting with questions—you'll ask smarter, more specific questions.
Take Notes Throughout the Day
Capture observations, terminology, and questions as they arise so nothing is forgotten.
Express Genuine Curiosity
People enjoy sharing expertise—show interest in what they do and why they do it that way.
Question Types by Shadowing Phase
Morning: Big Picture Questions
Mid-Day: Process Questions
End of Day: Reflection Questions
Common Pitfalls
Asking Only Generic Questions
Use what you observe to ask specific, context-based questions that show engagement.
Interrupting Critical Tasks
Read the room—save questions for natural breaks, not during high-stakes moments.