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Fifth year, and I also still do this, particularly with attorneys I haven’t worked closely with. Some will assume you’re stupid because you’re asking, others will appreciate that you want to do the project the way they prefer.
I think it’s fine to ask as long as it isn’t a really straightforward request. I’d be extremely annoyed if, as a partner, I instructed an associate to write me a memo on a specific question or to research a particular point of law and I got asked “how would you approach this”… like, you should know how to do those things without burdening the partner as a 5th year. But if the assignment is explained in vague or broad terms such that you can’t exactly discern what the partner is looking for/what is important to them, asking for more detail is fine.
Pro
There is no matter management system we're kind of trying to build one
I still do this and I’m in my 4th year.
Yes, that’s a good practice. Try not to be shy about asking the assigner more questions about what they want and how they want the final product to look, where they’d start, how much time they expect it to take, etc.
No, it’s my preferred approach when a jr or mid isn’t sure what to do. If rather explain first then then do it wrong and have to redo it and cause delays.
Better to ask than keep guessing or make mistakes that could be available if you asked. Nothing embracing about it.