[halfmatthalfcat]

I just had to talk with a couple more junior people on my team about this.

We're having difficulty on people wheel spinning and taking too long to reach out when there's problems but it's not because they can't but there's a sense you develop as you gain more experience on what that "red line" is when you need to reach out.

It's a combination of experience with the task (language, codebase, etc), agile point values (or just "level of effort") and how easy it is to approach those with the answers. As they're continuing to do work, evaluate where the time you've currently spent matches up to each of those three things. If you've hit that red line, time to start sounding alarm bells (relatively).

It really is a learned skill and takes time, juniors shouldn't feel bad and seniors/leads shouldn't make them feel bad. Seniors/leads should also be planning for learning this skill into their estimates to stakeholders.