Collab not syncing well after upgrading assets

This is something it has happened to me and my other member of our Collab team several times now. Very often when we upgrade some asset, (mostly the assets not using UPM). I upgrade the asset and sync changes to Collab but seems like my coworker doesn't get the exact same project I synced as he sees tons of compilation errors that Im not able to see or that I saw but I fixed before the sync.

This doesn't happens always but when it happens the only solution is to send him my project on a zip.
We are wondering if this is some Collab problem and if we were to change to GitHub or similar we would have the same problem.

Do other people have the same problems when upgrading 3d party assets? Is this something common?
Are we doing something wrong?

Please help on this.