Questions to Ask While Shadowing
Questions for the moments while you are watching someone work: what they just did, why they chose it, and what a beginner would get wrong. Useful whether you are shadowing a colleague during a handover, a tradesperson, or a mentor in your own field.
The questions
Open any question for the note
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.
How would someone new have handled that, and what would have gone wrong?
Why ask it
Asking about the beginner's version rather than your own keeps it comfortable to answer honestly. It also predicts your own first mistakes fairly accurately.
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.
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.
What did you get wrong for years before someone corrected you?
Why ask it
Long-standing misunderstandings are common, rarely written down and often widely shared. Hearing one is a shortcut past a mistake you would otherwise make for the same length of time.
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.
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.
Watching well
Practical guidance for the conversation itself
How to observe
Watch first, ask in the gaps
Note your question, keep watching, and ask when the task is finished or during a natural pause. A question asked mid-task can genuinely cost the person their place, and it is what makes hosts reluctant to take another shadow.
Track hands and eyes, not just words
Much of expertise shows up as where someone looks, what they check twice, and what they ignore. These are the details people forget to mention because they are no longer conscious of them.
Write down the words you do not know
Collect the jargon as it appears and ask about it in a batch later. Stopping to ask about each term breaks the flow, and half of them will be explained by context anyway.
Making your questions worth answering
- Anchor to something you just saw: at that point, when you did this, before you picked that up.
- Ask about one thing at a time, and let a pause happen before you add a second.
- Ask about the decision rather than the outcome, since the reasoning is what generalizes.
- Prefer how did you know over why did you do that, which can sound like a challenge.
- Repeat their answer back once in your own words to check you understood it.
- If the answer is that it depends, ask for the two cases where it goes different ways.
Being welcome to come back
Be visibly useful in small ways
Carrying things, holding a door, tidying up, staying out of the way in tight spaces. People remember whether you were easy to have around far longer than they remember your questions.
Treat what you see as private
Client names, prices, internal problems and half-finished work all count. Nothing goes into a post, a group chat or a conversation with a competitor, and no photographs without asking.
Write your notes up the same day
Turn the shorthand into full sentences while you still remember the context, and mark the questions you did not get to ask. Those become your first messages if you get a second visit.
Say thank you with something specific
One concrete detail you learned, sent the next day. It is short, it is easy, and it is the reason people say yes when you ask again.