Questions to Ask on Your First Day of Work
These twenty questions are for the people you will sit beside rather than the manager who hired you: teammates, the person assigned to show you around, whoever is nearest when you get stuck. They cover how the team actually works, as opposed to how the onboarding document says it does.
The questions
Open any question for the note
How long have you been here, and what were you doing before this?
Why ask it
The safest opener because everyone can answer it, and the length of tenure tells you how to weight everything else they say. Someone three months in remembers what confused them; someone nine years in knows why things are the way they are.
What do you actually work on day to day?
Why ask it
Job titles inside a company are usually inherited rather than accurate. The word "actually" gives people permission to describe the real job, which is often two thirds something that is not in their title.
How does work normally reach you, a ticket, a message, someone stopping by?
Why ask it
This is the fastest way to learn whether the team runs on a process or on interruption. If the answer is that everything arrives as a direct message, expect your own week to be shaped by whoever asks loudest.
Who do you go to when you're stuck?
Why ask it
Names two or three people who are the actual knowledge base regardless of seniority. If everyone names the same person, that person is a bottleneck, and being considerate of their time will make you popular quickly.
What's the busiest stretch of the week or the month?
Why ask it
Every team has a rhythm: a Monday planning crush, a month-end close, a Thursday release. Knowing it stops you from booking a long introductory chat with someone on the worst possible afternoon.
Which of these tools do people really use, and which are just installed?
Why ask it
Most companies have three chat tools, two wikis, and one place where decisions genuinely get recorded. Asking a peer, not a manager, is the only way to find out which is which.
What did you find confusing when you started?
Why ask it
Recent joiners answer this in detail and it maps the gaps in the onboarding material. Long-tenured people often say they cannot remember, which is itself a sign that nobody has updated the material in years.
How do people here take lunch?
Why ask it
Small, and it decides how quickly you get to know anyone. In some offices everyone eats at their desk and the social time is elsewhere entirely, so it is worth asking rather than sitting alone on day three assuming that is the norm.
Is there anything the team is tired of explaining to new people?
Why ask it
A quiet way of asking what you should look up instead of asking about. It also usually reveals a genuinely confusing part of the system that has defeated several previous hires.
Who will I work with a lot who isn't on this team?
Why ask it
Cross-team dependencies are invisible on day one and are where most of the delays live. Getting the names now means you can introduce yourself before you need something from them.
How much of this job turns out to be meetings?
Why ask it
Peers answer this honestly in a way managers often do not. The number, and the tone they say it in, tells you whether focused work happens during the day or after hours.
What happens here when something goes wrong?
Why ask it
Listen for whether the answer describes a process or a person's mood. "We do a write-up and fix it" and "we all keep our heads down" describe two entirely different places to work.
What's changed since you joined?
Why ask it
Gets you the recent history that explains the present: a reorganization, a system migration, a manager who left. Much of what looks illogical on your first week is a residue of something in that answer.
Is there anything my role is expected to fix?
Why ask it
Colleagues often know exactly why a position was opened, and it may not match what you were told in interviews. If two people give you the same answer, treat it as the real brief.
Who's the person everyone quietly relies on?
Why ask it
Rarely the most senior person, and rarely on an org chart. It might be an office manager, a long-serving analyst, or a support engineer. Knowing the name early prevents you from underestimating them.
What's the fastest way to annoy people here without meaning to?
Why ask it
Framed as a joke, answered seriously. Expect very specific answers: booking over someone's protected time, replying to all, moving a card on the board without asking. These are the things nobody documents.
What am I most likely to get wrong in my first month?
Why ask it
Better than asking for general advice, because it forces a prediction. If several people predict the same mistake, that is a system problem you have been handed, not a personal risk.
What's the best part of working on this team?
Why ask it
Ask it after the practical questions, when people are relaxed. Hesitation is data. So is an answer that is entirely about the people and never about the work, or entirely about the work and never the people.
What would you change about how the team works?
Why ask it
Most people will answer if you have already asked a few harmless questions and listened. Note the answers, do not act on them yet, and see how many of the complaints repeat across different people.
If you were me, what would you spend the first month learning?
Why ask it
A good closer because it asks for a recommendation rather than an opinion, and it flatters without flattery. Collect the answers from several colleagues and start with whatever more than one person named.
How to use these with new colleagues
Practical guidance for the conversation itself
Approaching people on day one
- Ask for fifteen minutes, not thirty, and end on time. People say yes to fifteen minutes on a day when they have work to do.
- Two or three questions per person is the right load. You are not interviewing them, and you will speak to them again tomorrow.
- Say plainly that you are new and orienting. Almost everyone is generous with a new hire in week one, and the goodwill fades, so use it.
- Ask the same question of three different people. Where the answers diverge is where the interesting part of the job is.
If you are starting remotely
- Nobody will stop by your desk, so schedule the introductions yourself. Short calls with five people in the first week beats one long group meeting.
- Ask early which channel is for real work and which is decorative. Remote teams often keep the actual decisions in a thread you have not been added to.
- Turn the camera on for first introductions if the team does, and match whatever they do afterward.
- Ask someone for the informal channel, whatever plays the role of the corridor. Remote joiners who never find it stay outsiders for months.
What not to do in the first conversations
Criticizing your last job
It is the most common first-week mistake and it is remembered longer than anything you say about your skills. Answer questions about your old employer plainly and without a verdict.
Comparing everything to how it was done before
"At my last company we..." in week one lands as a complaint, not a suggestion. Keep the observations in a note, and raise the useful ones in a month when you can explain why they apply here.
Asking colleagues about pay and progression
Perfectly legitimate questions in the wrong venue on day one. Take compensation, promotion, and probation terms to your manager or the people team instead.
Repeating gossip you were given
Somebody will tell you which manager is difficult or which team is a mess. Listen, verify nothing secondhand, and do not carry it to a third person. Being seen as a conduit in week one is hard to undo.
The first fortnight
- 1Day one: names, roles, where things are, who to ask when stuck. Nothing more ambitious than that.
- 2Days two to five: how work arrives, which tools matter, what the weekly rhythm is, and one short conversation with each person you will work with directly.
- 3Second week: the harder questions about what goes wrong, what people would change, and what your role is expected to fix. You now have enough context to understand the answers.
- 4End of the second week: write down the three things multiple people independently told you. Those are the real conditions of the job, and they will still be true in six months.