Questions to Ask When Shadowing
Questions for a day spent observing someone at work in any field, covering how they spend their time, which decisions are theirs, how the job is judged, and what you would need to do to get one like it.
The questions
Open any question for the note
How should I introduce myself if someone asks who I am?
Why ask it
Asking first spares your host the awkwardness of explaining you mid-meeting, and it tells you how much of the day involves people outside the team. It also signals that you understand you are a guest in someone else's working day.
What are you working on today, and where should I be for it?
Why ask it
Some of the day will be observable and some will not, and knowing which in advance stops you hovering during a confidential call. It also lets you spend the closed portions doing something useful.
What on this week's calendar is typical, and what is unusual?
Why ask it
A single day is a poor sample, and your host can tell you whether you are seeing the normal rhythm or an exceptional one. Without this you may draw a conclusion from a day that never repeats.
Which part of your job would surprise someone who only knows the title?
Why ask it
Every role contains work that is invisible from outside, often administrative, political or emotional. This is usually the largest gap between how a job looks from a job description and how it feels to do.
How much of your day do you actually control?
Why ask it
The difference between a calendar you own and one filled by other people is one of the strongest predictors of whether someone likes their job. It is also easy to misjudge from the outside.
Who do you depend on to get your own work done?
Why ask it
Most roles are limited by other teams, approvals or information from elsewhere. The answer maps the organization more accurately than any chart and shows where the friction is.
What does a good day here look like, and what does a bad one look like?
Why ask it
Two concrete days say more than any general assessment of job satisfaction. Notice whether the bad day is about the work itself or about the surrounding conditions, because those are different problems.
How did you get this job, and what was the step before it?
Why ask it
Career paths are usually less orderly than they appear on a professional profile. The step immediately before is the one you can plan around, and it is often not the obvious one.
What did you have to learn on the job that no course covered?
Why ask it
The gap between training and practice is where new starters struggle, and the answer is often about judgment, tools or navigating people. It tells you what to expect in a first year.
Which skill do you use every day that people underrate?
Why ask it
It is rarely the technical skill in the job title: more often writing clearly, running a meeting, or reading a situation. Whatever they name is something you can start practicing now.
How do you know whether you had a good month?
Why ask it
Formal metrics, a manager's opinion, or nothing at all: each produces a different working life. Roles with no clear measure of success can be liberating or unsettling, and it is worth knowing which this is.
Which decisions are yours, and which go up the chain?
Why ask it
Autonomy is the thing most often overstated in recruitment and most felt in practice. Asking for the boundary in specifics avoids the general answer about a flat culture.
What is changing in this field in a way that concerns you?
Why ask it
Practitioners see shifts earlier than commentary does, whether in tooling, regulation, funding or how the work is bought. Their concern is more informative than a prediction, because it is grounded in what they have already noticed.
What part of the work do you think will not exist in ten years?
Why ask it
This invites a candid assessment of which tasks are durable and which are being automated or outsourced. Useful for deciding what to build a career on rather than what merely looks busy today.
Who else here should I talk to, and why?
Why ask it
A second perspective from a different level or function corrects the impression a single day gives. Being asked also flatters your host's judgment, so it usually produces a genuine introduction.
What do people in your role usually leave for?
Why ask it
The exits tell you what the ceiling looks like and which adjacent roles this one leads to. If everyone leaves for the same reason, that reason is the defining feature of the job.
What would you look for on an application for an entry-level version of this job?
Why ask it
You get a hiring manager's filter rather than a published requirement list, and the two often differ. Ask what would make them stop reading, since that is the more actionable half.
If I want a job like yours, what should I do in the next six months?
Why ask it
Bounding it to six months forces something concrete: a course, a portfolio piece, a specific kind of role to take first. Open-ended versions of this question produce advice you cannot act on.
What did you get wrong about this work before you did it?
Why ask it
Their earlier misconception is probably yours too, since you are looking at the job from where they once stood. It is the most efficient correction available in a single day.
Is there anything from today I should not repeat outside this building?
Why ask it
Asking before you leave protects your host and makes a second visit possible. In many settings there will be something, and they will be relieved to be asked rather than having to raise it.
Getting the most from the day
Practical guidance for the conversation itself
Before you arrive
Ask three logistical questions
What time to arrive, what to wear, and whether you need to be signed in or badged. These are the things that make a first impression before anyone has heard you speak.
Do the reading you can do yourself
Look up the organization, the team's work and the vocabulary of the field. Spending the day asking what things are called wastes the part of the visit that cannot be replaced.
Send two questions ahead
A short note with the two things you most want to understand gives your host a chance to arrange something relevant, such as sitting in on a particular meeting.
During the day
- 1Save questions for gaps: travel between locations, a walk to lunch, the quiet hour after a meeting.
- 2Keep a running note of anything that surprised you, and use it at the end of the day.
- 3Watch how people talk to each other as closely as what they are working on.
- 4Offer to be useful in small ways, and accept being told there is nothing to do.
- 5Do not ask for a job during the visit, and do not photograph screens or documents.
- 6Ask before you leave what you should not repeat, and who else you might speak to.
Afterwards
Write it up the same day
One page: what the work actually consists of, what you liked, what you did not, and what you now want to check. The detail fades quickly and it is what makes the visit worth having done.
Send a specific thank you
Name one thing you learned and one thing you plan to do because of it. Generic thanks are forgettable, and this is the message that keeps the door open.
Follow the introduction
If they named someone else to talk to, contact that person within a week and say who suggested it. This is how one day turns into a useful set of contacts.