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

Question

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?

Rahul Pandey · Accepted Answer

Part of this just comes with seniority and more time in the organization.

But I think you can also do a bit of historical analysis to see what kind of things people have asked about to calibrate what kinds of questions get asked. This can also show you what/if has changed about tools or utilities that are blocking you. You can reference these posts in your question to demonstrate that you did the legwork.

Two more suggestions:

can you create/cultivate an informal peer group where you can ask lightweight questions? tI can give you one more signal on “escalate if no one in that smaller group of friends knows the answer to your question".
In general, I would bias toward escalating early, especially if you have a dedicated point of contact like a mentor or Tech Lead who has offered help. This goes back to the idea that over-communication is better than under-communication. If there is a real issue, then you and the whole organization will want to have heard about that as soon as possible.

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

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