Questions to Ask When Shadowing
Questions to ask someone you are shadowing at work, in any field: 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 last group is a list of questions to ask a CEO when shadowing one, where the day is mostly meetings and the work is harder to see.
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The questions
Each question, and why to ask it
The day and the job
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.
While you watch
Can you tell me what just happened there, in your own words?
Why ask it
Asked immediately after something you watched, this gets you the version with reasoning in it. Asked an hour later it gets you a summary, which is much less useful.
What were you looking at when you made that call?
Why ask it
Experts read cues they no longer notice themselves: a number on a screen, a tone of voice, the order things arrived in. Naming the cue is the transferable part of the skill.
What did you notice there that I probably missed?
Why ask it
Puts the burden on them to compare your attention with theirs, which is where the gap between novice and expert actually sits. Expect two or three things you had no idea were relevant.
Where in that process is it easiest to get wrong?
Why ask it
Every procedure has one or two steps that carry all the risk while looking as routine as the rest. Learning which ones they are tells you where to slow down when it is your turn.
What is the step people skip, and what happens when they do?
Why ask it
The consequence is the memorable part, and a good answer usually comes with a story about someone. That story will stay with you far longer than a checklist.
Why that tool or method and not one of the alternatives?
Why ask it
Sometimes the reason is sound and sometimes it is what the organization bought in 2014. Both answers are worth having, and only one of them is in the manual.
What are you doing out of habit rather than necessity?
Why ask it
Practitioners can usually separate the two if asked directly, and the honest ones enjoy the question. It stops you copying rituals as though they were requirements.
Are you breaking any of the official rules right now, and why is it acceptable here?
Why ask it
Real work almost always departs from the written procedure somewhere. Understanding which departures are safe and locally accepted, and which would get someone in trouble, is knowledge you cannot get from documentation.
How do you know when this is finished?
Why ask it
Beginners either stop too early or polish forever, because nobody told them the standard. A specific stopping condition is one of the most useful things you can take away from a day of watching.
What are you keeping track of in your head that is not written down anywhere?
Why ask it
This is the informal system that keeps the place running: who to call, what always breaks, which order things have to happen in. It is also what disappears when someone leaves.
What went wrong the last time you did this?
Why ask it
Past tense and specific, so it is easier to answer than a question about mistakes in general. The failures show you the parts of the process that exist for a reason.
How long did this take you when you started, and how long does it take now?
Why ask it
Sets a realistic expectation for your own learning curve and prevents you concluding you are hopeless in week two. The ratio is usually larger than beginners assume.
If this went badly, who would you call, and at what point?
Why ask it
Knowing the escalation path, and the moment at which experienced people stop trying to fix things alone, is a skill in itself. Beginners typically escalate far too late.
What would you not let a new person do unsupervised yet, and why?
Why ask it
Tells you where the real risk lives and gives you a map of what you would learn in what order. It also frames your own limits without either of you having to be awkward about it.
Could I try a small piece of this, and what should I be careful about?
Why ask it
Ask once, accept a no without pushing, and ask about the risks in the same breath so it is clear you understand there are some. Doing five minutes of the work teaches you more than three hours of watching.
What should I practice first if I wanted to be useful around here?
Why ask it
Shifts you from observer to potential contributor, which changes how people treat you for the rest of the time. Answers are usually smaller and more specific than you expect.
How did you learn this, and would you learn it that way now?
Why ask it
Training routes change, and the person in front of you knows which parts of theirs were wasted time. This is where you find the course, book or apprenticeship worth pursuing.
What should I be watching for the rest of the time I am here?
Why ask it
Hands the agenda back to the person who knows what is coming up. It usually produces a heads-up about something later in the day you would otherwise have watched without understanding.
Shadowing a CEO
When we are in a room with customers, investors or the board, should I take notes, speak, or stay silent?
Why ask it
A chief executive's meetings often include people who were not told a visitor would be there. Settling this before the first one means nobody has to manage you while the meeting is running.
Who decides what reaches your calendar, and what gets turned away?
Why ask it
At this level the scarce thing is attention, and somebody is rationing it, whether that is the CEO, an assistant or a chief of staff. The rules they use tell you what the company treats as important this month.
What does your assistant or chief of staff handle that I would not guess?
Why ask it
You will probably spend part of the day with this person, and they often see more of how the office runs than anyone. Asking the CEO first also gives you a natural opening to put the same thing to the assistant later.
Which meeting today mattered most, and what were you trying to get out of it?
Why ask it
From a chair at the side of the room, eight meetings look alike. Knowing which one carried the weight lets you replay it in your head and see what was being steered.
What do you look at first each morning to know how the company is doing?
Why ask it
Most leaders have two or three numbers or messages they check before anything else. Ask why those ones, because the choice shows what they think actually drives the business.
How does bad news reach you, and how long does it usually take?
Why ask it
The further up someone sits, the more the information arriving has been tidied on the way. A leader who has thought about this will describe a specific habit, such as skipping a level or walking the floor, and you may see it happen during the day.
Who do you answer to, and how often do you hear from them?
Why ask it
It might be a board, a founder, a family, investors or a parent company, and each makes for a different job under the same title. From outside it is easy to assume the person at the top answers to nobody.
How do you divide your attention between this year's results and where the company should be in five?
Why ask it
Nobody else in the building is asked to hold both at once to the same degree. A concrete answer usually names days or meetings set aside for the longer view, which you can then look for on the calendar you are following.
What did you have to stop doing yourself when you took this job?
Why ask it
Many people reach the top by being good at a craft they then have to hand to others. Listen for whether they miss it, since that is a fair preview of the trade you would be making.
Which part of the business do you understand least, and how do you lead it anyway?
Why ask it
No chief executive has done every job that reports to them. How they run an area they could not do themselves, through questions, trusted people or numbers, is a part of leading you can start practicing in any role.
What do people stop telling you once you have the title?
Why ask it
Candor thins out as seniority rises, and leaders who know it tend to be frank about the gap. Their answer also tells you how plainly you can speak to them for the rest of the visit.
Who do you talk a hard decision through with when it cannot be anyone inside the company?
Why ask it
Some decisions involve the very people a leader would normally consult. Whether the answer is a mentor, a peer at another firm, a coach or nobody says a good deal about how lonely the role is.
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.
If you are shadowing a CEO
Set the visit up through their assistant and ask which meetings you can sit in on and which you should step out of. Agree a fixed ten minutes for your own questions at the start or the end, because a chief executive's day rarely leaves a gap by itself.
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.