How do you get better at identifying when to escalate an issue?

I’ve gotten feedback that I should ask questions earlier, and my manager mentioned that it’s always a tricky balance between working independently and looping others in. But in practice, I find this really hard to navigate.

For example, I try to be thoughtful about when I ask questions, especially when working with senior engineers. I’ll usually wait until I’ve tried multiple approaches and then time my questions for the morning, since responses can take a while. In the past, I’ve asked questions and ended up blocked all day waiting for a response, so I try to avoid that.

But the core issue is this: I often can’t tell when something is worth escalating. I don’t have a strong internal signal for when I should reach out to a senior engineer, a different team, or even a PM or manager. I genuinely don’t have know how to recognize when something is beyond me or when I should keep pushing on my own.

Any tips?