A while back I saw a clip of The Ellen DeGeneres Show where Ellen played Never Have I Ever with Johnny Depp, Gwyneth Paltrow and Paul Bettany. It was hilarious! (You can watch it here.) I thought – HEY, that would be a fun icebreaker to do with district leaders!
I can tell you now, from personal experience, that it is a MOST ENJOYABLE icebreaker to do with your staff or team! I can’t remember the last time we all laughed that hard! In fact, those paddles were held up long after the icebreaker was over in support or denial of statements throughout our leadership retreat, eliciting further chuckles.

This is nothing groundbreaking or particularly creative, but I am sharing the questions I asked and a printable PDF of the I Have / I Have Never cards in case you need something fun to do with your staff to kick off the year. It is super easy – I just printed the cards on cardstock, then folded them over, cut them in half and glued a popsicle stick in the middle.
Never Have I Ever Questions
- Worn two different shoes to work
- Fallen asleep at my desk
- Laughed at a student’s inappropriate joke
- Taken work home that never made it out of the car
- Yelled at my computer screen
- Fallen in the hallway of my school or building
- Cleaned my desk by piling everything into one stack
- Dozed off during professional development
- Rolled down the hallway in my office chair
- Played on my phone while trying to look like I am doing something important
What is your favorite icebreaker to do with staff upon returning from summer break?