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I recently sent my materials to a large regional law firm with a great reputation. They expressed interest and requested additional materials. Previously I worked with a former senior associate from the firm. Would it be weird or a mistake to message the former associate about the position and simply request "pointers" with the hope of getting pointers and possibly an offer to make a call or send an email on my behalf? I just want to maximize my chances of getting the position. Thoughts?

I should add that this senior associate did not jump ship to a different firm, but went in-house. If that matters at all.

Yes, you should absolutely contact him and ask for advice. Don't be too blunt about asking him to make a call on your behalf, though. He'll know what's up when you contact him and, if he's comfortable doing so, offer to help.

Thanks for the advice. Email sent.