When I was a manager of a small team it was all junior guys. I had to hammer into their heads to message if they had trouble making progress.

A few times I got the feeling one of the guys was having issues (based on messages). So I called them up on Friday afternoon and they admitted they were way behind because they couldn't get past an issue. But they said "don't worry, I'll work through the weekend to get it done".

I told him "no, you're not working on the weekend. We'll connect on Monday morning and work through the problem together. Just let me know sooner next time so we can get you back on track quicker."

After a couple of those they got the message that it's ok to ask for help and isn't a sign of weakness and they're not gonna get fired for asking.