Avoid awkward welcome lunches with these fun prompts

June 7, 2022

It’s your new hire’s first day and you’ve set up a welcome lunch for them. You’re hoping to introduce them to everyone and help them get to know the team. 

When you worked in an office, this was an easy task. All you had to do was order some food and book a meeting room or set aside a table in the cafeteria. Then the conversation would just flow from there. 

The people sitting next to your new hire could chat with them the most. And the people sitting further away could naturally chime in, or they could talk to each other. Mingling in person was an easy way to socialize, especially in a group setting. 

But things have obviously changed since then. And if your company has adopted a remote or hybrid work model, hosting a digital welcome lunch is an entirely new beast to wrangle. 

Why remote welcome lunches can feel awkward

On Zoom or Google Meet, you can’t make eye contact, so it’s difficult to communicate and interpret social cues, which makes having a free flowing conversation a tall order. Even worse, there are no side conversations for people to bounce between, so only one person speaks at a time. That means the spotlight is completely on your new hire. And since there’s really only one conversation going on at a time, anyone who’s speaking has to cover a topic that’s relevant to everybody. 

This lends itself to a lot of Q&A, which is great for getting to know your new hire, but it can also limit the kinds of questions people can ask them. And if your team runs out of questions to ask, the dreaded awkward silence will rear its ugly head and make everyone want to hit the “End Meeting” button immediately. 

Fortunately, you can sidestep the awkward zoom lunch by preparing a list of fun prompts in advance. Answering these prompts will let your new hire give their new teammates a glimpse of their personality that their LinkedIn Profile can’t offer. And it can also spark entertaining tangents that everyone can contribute to, which can lead to your teammates finding out that they share common interests with your new hire. This can trigger individual conversations between them that will build rapport and forge a connection. 

Here are 30 prompts that you can ask your new hires during their welcome lunch, categorized by get-to-know-yous, would-you-rathers, and hypotheticals. Read on to start turning remote welcome lunches into the best part of everyone’s day. 

30 fun prompts that’ll turn remote welcome lunches into the best hour of the day


  1. NSYNC* or Backstreet Boys?
  2. Skittles or Starburst?
  3. What’s your secret obsession?
  4. What’s your spirit animal and why?
  5. What’s your guilty pleasure?
  6. What’s your go-to dance move?
  7. What’s your go-to karaoke song?
  8. What was your first concert?
  9. What is your worst roommate story?
  10. As a kid, what did you want to be when you grew up?

Would you rather

  1. Would you rather have claws for hands or wheels for feet?
  2. Would you rather fight off 100 chicken-sized horses or 1 horse-sized chicken?
  3. Would you rather listen to one song for the rest of your life or never be allowed to listen to the same song twice?
  4. Would you rather go back in time to meet your ancestors or go into the future to meet your great-grandchildren?
  5. Would you rather have front row tickets to a musician you’ve never heard of or listen to your favorite band perform from the parking lot?
  6. Would you rather live in a new country every month or never go on vacation again?
  7. Would you rather drink a glass of ketchup through a straw or eat a bowl of mayo with a spoon?
  8. Would you rather eat nothing but salad or nothing but dessert for a week?
  9. Would you rather take a bath in salad dressing or shower in barbecue sauce?
  10. Would you rather have a dog that looks like a baby or a baby that looks like a dog?


  1. If you could be any movie or television character, who would you be?
  2. You have magically received $1,000,000 but you have to spend it in 24 hours. What is your plan?
  3. You just became a ghost. What’s the first thing you do?
  4. If you could choose one thing from science fiction to exist in the real world, what would it be?
  5. If you could possess a sixth sense, which one would it be?
  6. You find a book about your life, and you get to the point that you’re at right now. Do you flip the page and keep reading or do you stop? Why?
  7. Everyone has a button that you can press, and it will do something. What does your button do?
  8. If you were a dog, which dog breed would you be?
  9. If you had unlimited funds, what would you do with your life?
  10. If you could only go back in time once, which time period would you go back to and why?

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