Tips and techniques

5 non-cringey back-to-work questions for your team

Ben Crothers Ben Crothers • 6 January 2025

Do you want to get your team bonding together after the holiday break, but don’t want it to come off cheesy or cringey? Try a question or two from this list.

Image for this blog post

Happy New Year! You might be back at work already, or soon to return to work. Chances are, you’re in for several tedious exchanges with fellow colleagues... Cue the yearly joke “I haven't seen you since last year”. Cue the monotonous to-and-fro of generic reports of “I ate too much”, and “Now I forget what I do around here”.

This can get even more tedious in that first team check-in meeting of the year, if the whole team has to answer some boring or cringey question to get everyone in the ‘back-to-work’ mood.

Of course, it IS a great idea to get everyone back into the swing of things. It IS a great opportunity to get the team bonded a bit more. If you manage a team, or run any team meetings, skip the question about “favourite part of your holiday break”, and try these ideas instead.

1: What have you learned that will help you this year?

Let’s start with a couple of reflection questions. I always like setting a tone of ongoing learning and improvement in projects and meetings I’m part of, so I really like this question. It encourages everyone to reflect a bit more deeply on the previous year (or previous project... whatever the context is).

2: What’s something you’re grateful for from last year?

Setting a tone of gratitude in a group can also be really positive, and what better way than to ask everyone about something they are thankful for? Variation: What’s something you want to celebrate about last year, even if it felt small at the time?

3: Cheesy Check-in

Sometimes it’s fun to just embrace the cheesiness of the situation, and that’s where the Cheesy Check-in activity can help. Ask everyone where they’re at when it comes to starting up work again after the break, and to pick an image from the Cheesy Check-in board that best represents their answer.

Feel free to save this image and print it out, so that people can circle or put a dot on the image that best represents their mood. If you’re working online, you can use this free Miro template I made; just ask people to place one of the dots provided on the photo that best matches their mood.

A 3x3 array of 9 really cheesy cliche stock photography images
The Cheesy Check-in panel, with all credit helpfully displayed to various stock image libraries wherever possible

4: What’s a word that represents your intention for the year, and why?

Let’s turn to questions about the future, and a question about setting positive intentions can be really cool. It can help everyone in the team to focus on what’s most important about what they individually – and perhaps collectively – want to be throughout the coming year. What I like about this is that it’s not about goals (as important as they might be), but more about why those goals are important.

Ask everyone to have a think, and then share their word (or short phrase). It’s totally fine to let each person explain why that word is important for them. Some examples others have come up with in meetings I’ve run when I’ve asked this question:

  • Curiosity - as in: approach all situations with more curiosity, especially tough conversations at work
  • Courage - this was in the context of making decisions faster
  • Nurture - for this person, it meant making sure her own cup was full before helping others fill their cups

Encourage everyone to affirm each other, and perhaps reflect on any similarities or themes that emerge.

Bonus move: Ask everyone to get a bit creative, and write their word in large letters on a large piece of paper, and stick the paper up in a common area, as a reminder for everyone throughout the year.

5: What’s one skill or area of knowledge you’d like to grow in this year?

This is such a great question! It’s also perfectly fine for people to keep going with a skill or area of knowledge they’ve already been working on. Bonus part to the question: "and how can the team support you?"

Bonus question: What’s a regular habit or routine you want to embrace this year to help you feel more productive?

James Clear’s book Atomic Habits had a big effect on me and how I invest in small but regular habits to improve myself. Big changes — in any area that is important to your team — can happen not so much from drastic changes in processes and systems, but from consistently applying those little changes. This can be a great area for you and your team to focus on at the start of the year.

So, there you have it. Ditch the "So, how was your break?" and give one or more of these questions a go in your ‘return to work’ team meetings. I really hope they inspire more insightful impactful discussions.

Get power moves in your inbox every week

Subscribe to our newsletter, and receive news, tips and resources to help you have a better impact at work.

Keep learning

What if Super Mario ran your next meeting?

7 April 2025

What if your next meeting felt less like a chore and more like a Super Mario Bros. level, with a clear goal, visible progress, and a little fun along the way? Try this Meeting Steps framework...

Use the Meeting Bento Box to stop overstuffing your meetings

3 April 2025

Learn how drawing the Meeting Bento Box framework can help you fit the right topics into the right meeting time, without the chaos or leftovers.

Other categories to dive into

ResourcesUpdates