40 Icebreaker Questions for New Employees — First Day, First Week, First Month

Remote onboarding is harder than it looks. Without the natural friction of a shared physical space — bumping into people in the corridor, overhearing conversations, sitting near different people every day — new hires can go weeks without knowing the people they work with at anything more than a surface level.

Icebreaker questions, used deliberately at the right moments in the first month, close that gap faster than any onboarding document or company Notion page.

Here are 40 that work, organised by when to use them.

First day questions (keep these light — the goal is welcome, not depth)

These go in the first team meeting or standup the new hire attends. The objective is to give the team something to know about the person beyond their name and role.

1. What's something you're hoping to learn or experience in this role that you haven't had the chance to do before?
2. What's the best piece of advice you got before starting here?
3. Where are you calling from today, and what's the setup like?
4. What's one thing people are usually surprised to learn about you?
5. What are you most looking forward to about working with this team?
6. What does a great day at work look like for you?
7. What's something you need from a team to do your best work?
8. If you could only describe yourself in three words, what would they be?
9. What's something completely unrelated to work that you're passionate about?
10. What's the last thing you learned that genuinely excited you?

First week questions (now that the initial nerves have settled)

Use these in one-to-ones, buddy calls, or small group introductions during the first week. The goal shifts from welcome to genuine getting-to-know-you.

11. What's something about how you work that you'd want the team to know early?
12. What's a project you've worked on that you're most proud of?
13. How do you prefer to receive feedback?
14. What's something you find challenging that you're actively trying to get better at?
15. What does collaboration look like at its best for you?
16. What's the most interesting problem you've worked on in your career?
17. What's something you wish your previous team had done differently?
18. What's a skill or area of knowledge you have that's underutilised in your day-to-day work?
19. What kind of work do you find most energising?
20. What's something you're working on outside of work right now?

First month questions (once they've found their feet)

These go in retros, team sessions, or one-to-ones at the end of the first month. The goal is integration and honest two-way conversation.

21. What's been the most surprising thing about working here so far?
22. What's something you expected that turned out to be different?
23. What's one thing the team does that you think works really well?
24. What's one thing you'd do differently if you were designing this team from scratch?
25. Who on the team have you had the least interaction with so far, and how can we fix that?
26. What's something you've learned in the first month that you didn't know before?
27. What does your ideal working rhythm look like on a typical week?
28. What's something you wish you'd known before you started?
29. What's been the most valuable conversation you've had so far?
30. What would make your second month better than your first?

Team questions to ask about the new hire (run these with the existing team)

These go in a team session before or shortly after the new hire joins. The objective is to prepare the team to actually connect with the new person.

31. What do you remember most about your own first day here?
32. What's one thing you wish someone had told you when you joined that you could pass on?
33. What's something about working here that took you longer to figure out than it should have?
34. What's the best way to get someone up to speed on how this team actually works?
35. What's one thing about this team that an onboarding document would never capture?

Fun questions that work at any point in the first month

These can be dropped into any team meeting, buddy call, or standup as quick warmups.

36. What's the most unusual job you've had before this one?
37. What's a place you've worked from that wasn't a home or an office?
38. What's something on your bucket list that you've already ticked off?
39. If you had a completely free week with no obligations, what would you do?
40. What's something you'd want to be famous for, even if it's completely trivial?

Making the questions work

The questions are tools, not rituals. Don't read them from a list on a call — work them into natural conversation. The buddy system works well: pair the new hire with a team member for the first few weeks and give the buddy two or three questions from the relevant section to ask in their first coffee chat.

If your onboarding includes a group welcome call, Two Truths and a Lie is a reliable opener that gives the new hire a chance to reveal something about themselves while the team tries to guess the lie. It removes the pressure of being put on the spot while still surfacing real information.

One more thing: before a new hire's first day, a group welcome card where every team member has left a message or short video goes further than most teams realise. WishWarmly makes this straightforward — the team contributes async, the new hire receives it on their first morning. It signals that the team invested time before they even arrived, which sets a tone that no onboarding document can replicate.

The questions get the conversation started. Everything else builds from there.