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I am a team manager, on status meetings on fridays I always ask if someone has good plans for the weekend, and on monday I ask how was your weekend.
I get a lot of silence, and most of the time I tell some bits of what I did, but from time to time someone tells something about what they did.
I think that is good for the team, since we are all remote, it's a little bit of socializing and have something to talk about other than work.
At my old organisation we always had mandatory "check ins" at the start of weekly meetings where everyone took turns saying whatever was on their heart and how their day was going.
Always a bit awkward at first with a new team, but a month in and people would really open up, and it was really helpful as manager to figure how people were holding up. Especially during covid/lockdown.
Any examples of stuff that felt awkward at first and then was less awkward as time went on?
Just your typical stuff.
When you first start and can tell on their body language that they aren't fully comfortable and don't know what to share. You'll get the usual boiler plate answer like "it's all fine", "looking forward to start working", "it's sunny today so I'm happy", etc...
After a month or two people will be a lot more relaxed and comfortable sharing whatever is on their heart. You could end up hearing a minutes long ramble summarising someone's week, or if they are tired whey would usually say so and explain why.
It really helped to get people familiar and comfortable with each other despite the meetings being there primarily for work. Having people getting comfortable being open and honest is a godsend for whoever is managing the team.
It's one of the things that everyone would be positive about when we did one to one meetings with everyone in the org twice a year.