Starting a new job is awkward for everyone. The new person doesn't know where the stapler lives, and the rest of the team isn't sure how chatty to be. A few good questions fix that fast. They turn a stranger at the next desk into someone you actually know, and they make the newcomer feel wanted instead of tolerated, which matters more than most of us remember.
Below you'll find 150 questions sorted by how well you know each other. Start with the easy openers, then work toward work style, life outside the office, and bigger goals. Pick a couple at a time. Nobody wants an interview on their second day. Mix in a funny one when the mood is light, and save the goal questions for a relaxed lunch or a walk back from a meeting.
Easy Openers for the First Week
Start light. These are the questions you can ask at the coffee machine or while you wait for a meeting to start, and nobody feels put on the spot.
- How has your first week treated you so far?
- Where were you working before you landed here?
- What made you say yes to this job?
- Did you move to town for this role, or were you already local?
- How long is your commute, and how do you spend it?
- Have you found a decent lunch spot near the office yet?
- Is this kind of work new for you, or have you done something similar before?
- What surprised you most on your first day?
- Has anyone given you the grand tour of the building?
- What's the best piece of advice you've gotten here so far?
- Are you a morning coffee person or a tea person?
- Which part of onboarding felt the most useful?
- Did you have any time off between your old job and this one?
- What name do you like to go by around here?
- Is there anything you're still trying to figure out about the office?
- How did you first hear about this company?
- What did your friends say when you told them about the new job?
- Are you the kind of person who eats lunch at your desk or gets out for a walk?
- Do you know anyone else here from before?
- What's one thing that's been easier than you expected?
- Have the meetings been manageable, or is it a firehose right now?
- Which tool or system has been the trickiest to learn?
- What do you usually listen to while you work?
- Is there a question you've been too shy to ask anyone yet?
- Would you like me to introduce you to a few people on other teams?
Getting to Know Their Work Style
A few honest questions here save weeks of guesswork later. You'll learn how they like to communicate and when they do their best work.
- Do you prefer a quick chat or a written message when something comes up?
- What time of day do you feel sharpest?
- How do you like to get feedback, in the moment or saved for later?
- Are you a detailed planner or more of a figure-it-out-as-you-go type?
- What does a really good workday look like for you?
- How do you keep track of your to-do list?
- When you get stuck, do you like to puzzle it out alone first or ask right away?
- Do you work better with music, silence, or background noise?
- What kind of meeting do you find most useful?
- How do you feel about people dropping by your desk unannounced?
- Which projects from past jobs are you proudest of?
- What skill are you hoping to build in this role?
- Do you like having a clear process, or would you rather invent your own?
- How do you usually wind down after a busy stretch?
- What's a work habit you picked up that you'd never give up now?
- Are there any pet peeves I should know about so I don't step on them?
- How do you handle a day when everything lands on your plate at once?
- Would you rather split a big task into pieces or finish it in one push?
- What's something a manager once did that really helped you?
- Do you like to brainstorm out loud or think quietly first?
- How do you prefer to celebrate when a project wraps up?
- What does being a good teammate mean to you?
- Which part of this job are you most excited to dig into?
- How do you like to hand off work when you go on vacation?
- Is there anything about how you work that people often misread?
Questions About Life Outside the Office
People are more than their job titles. These help you find the hobbies, pets, and weekend plans that turn a coworker into a friend.
- What do you usually get up to on the weekends?
- Do you have any pets, and do you have pictures?
- What hobby could you talk about for an hour straight?
- Is there a sport or team you follow?
- What's the last show you couldn't stop watching?
- Are you into cooking, or more of a takeout person?
- What's a book you'd hand to a friend without a second thought?
- Do you have any trips coming up that you're excited about?
- Where did you grow up?
- What's your favorite way to spend a rainy afternoon?
- Are you part of any clubs, leagues, or groups outside work?
- What's a skill you've been meaning to learn for years?
- Do you play any instruments, or did you as a kid?
- What's the best meal you've had in this city so far?
- Are you more of a beach vacation or mountain vacation person?
- What's a local spot you think is underrated?
- Do you have a garden, or any plants you're trying to keep alive?
- What does a perfect Sunday morning look like for you?
- Are you into any board games or video games?
- What was your first job ever?
- Is there a concert or event you're looking forward to?
- What's a small thing that always puts you in a good mood?
- Do you have family nearby?
- What's the most interesting place you've ever lived?
- If you had a free Friday afternoon, how would you spend it?
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Fun and Lighthearted Icebreakers
Good for team lunches, a slow Friday, or the start of a video call. Silly questions often lead to the best stories.
- What's the strangest job interview question you've ever been asked?
- If the office had a theme song, what would you pick?
- What snack would you want stocked in the break room forever?
- Which fictional character would make the best coworker?
- What's your go-to karaoke song, even if you'd never actually sing it?
- If you could swap jobs with anyone here for a day, who would it be?
- What's the funniest thing that happened at a past job?
- Would you rather have a four-day week or a daily two-hour lunch?
- What's a food you refuse to eat no matter what?
- If you could add one odd perk to this company, what would it be?
- Which party trick of yours never fails to get a laugh?
- Which emoji do you use way too often?
- If your desk plant could talk, what would it complain about?
- What's a fashion choice from school you hope nobody here ever sees?
- Would you rather present to the whole company or clean out the office fridge?
- What was your dream job when you were a kid?
- Which decade's fashion would you bring back?
- What's a word you always spell wrong?
- If you had to eat one cuisine for a year, which one wins?
- What's the oddest thing in your junk drawer right now?
- Which movie do you know almost every line of?
- What's a small victory you had this week?
- Are you a pineapple-on-pizza person or not?
- What's the best costume you've ever worn?
- If you could instantly master one language, which would you choose?
Learning About Their Goals
Once you know each other a bit, ask about where they're headed. It shows you care about more than the next deadline.
- Where do you hope this role takes you in the long run?
- What would make this job feel like a win a year from now?
- Is there a type of project you'd love to get your hands on?
- Who's someone in your field you look up to?
- What's a career move you're glad you made?
- Have you ever changed careers, and what pushed you to do it?
- What part of your work do you want to get better at?
- Would you ever want to manage a team someday?
- What's a class, course, or certificate you've thought about taking?
- How do you measure whether a job is a good fit?
- What did your last role teach you that you're bringing here?
- Is there a mentor who shaped the way you work?
- What kind of problem do you enjoy solving the most?
- Do you have a side project you're building on your own time?
- What would your ideal job look like if titles didn't matter?
- How do you keep learning when things get busy?
- What's a goal you set for yourself this year?
- Is there a risk you've taken at work that paid off?
- What conference or event would you love to attend?
- How do you decide when it's time to move on from a job?
- What's one thing you'd like people here to know you're good at?
- Is there someone on the team you're hoping to learn from?
- What does success look like to you outside of work?
- Which past boss brought out your best work, and why?
- How can I help you settle in faster?
Practical Questions to Help Them Settle In
Being helpful early builds trust fast. Use these to spot what they need and point them the right way.
- Do you have all the logins and access you need yet?
- Has anyone explained how we book conference rooms?
- Would it help if I shared the notes from last month's team meetings?
- Do you know who to call when the printer jams?
- Are there any acronyms you keep hearing and don't understand?
- Have you been added to the right group chats and email lists?
- Do you know when payday falls and how expenses get handled?
- Would you like to sit in on one of my calls to see how they run?
- Has your desk setup been comfortable, or do you need a better chair?
- Do you know about the team lunch we do every other week?
- Is there a process here that seems confusing or backward to you?
- Would a quick walkthrough of our shared drive be useful?
- Have you met the folks in IT yet?
- Do you know how people usually ask for time off here?
- Is anything about the parking or transit situation a pain?
- Would you like a heads-up on which meetings are optional?
- Has anyone told you about the unwritten rules around here?
- Do you have a buddy or mentor assigned, or should we find you one?
- Which of our clients or projects have you heard about so far?
- Do you know where the good quiet spots are for focused work?
- Would you like to grab lunch with a few of us this week?
- Is there a question you wish someone had answered on day one?
- Do you know the best way to reach our manager when it's urgent?
- What would make your second week smoother than your first?
- Can I check back in with you next Friday to see how things are going?
How to use these questions
- Ask one or two questions at a time and actually listen to the answer before moving on.
- Share your own answer too, so it feels like a chat and not a quiz.
- Save the personal questions for later in the week, once the newcomer seems relaxed.
- Follow up a few days later on something they mentioned, like a trip or a pet's vet visit.
Frequently asked questions
What should I ask a new coworker on their first day?
Keep it simple and low pressure. Ask how the morning is going, where they worked before, and whether they've found the break room and a good lunch spot. Offer to answer any questions they have. The goal on day one is to make them feel welcome, not to learn their life story in a single conversation.
How do I avoid being too nosy with a new coworker?
Stick to work, hobbies, and light topics at first, and skip questions about salary, health, relationships, or politics. Watch their body language. If they give short answers, back off and try again another day. Sharing a little about yourself first also helps, because it signals what kind of topics feel comfortable to talk about.
Are these questions good for remote coworkers too?
Yes. Most of them work just as well on a video call or in a direct message. For remote teammates, the practical questions matter even more, since they can't just lean over and ask someone where a file lives. Try a short virtual coffee chat in their first week and pick a few questions from each section.
How can I help a new coworker feel included?
Invite them to lunch, add them to the team chat, and introduce them to people outside your department. Check in after a week or two to see what's still confusing. Small gestures like saving them a seat at a meeting or explaining an inside joke go a long way toward making someone feel like part of the group.