Two LoRs from the same Job?

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Welshman

He runs like a Welshman
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Hi
So here's my situation. I've worked at my schools IT center for the past 3 years and I basically have 2 bosses, one I work with every day and another who is a professor and dean at the school. Initially, I asked my daily boss for the letter since she knows me the best but recently I've been told that the dean writes great, well written, very strong letters and I'm sure he would write one for me as well (were also close, but I don't see/work with him quite as often).

My daily boss has already submitted the letter to my school's letter writing committee but mine is the first medical school LoR she has written before. So while I'm sure she said great things about me, it is her first letter.

In total have 4 letters so far and my committee will take a maximum of 7 so I'm fine in that respect but would they look down on having two letters from the same experience? If I'm confident that the dean will write me a strong letter should I ask?

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