LOR from work? Will this work?

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Hi everyone,
I am planning to apply to the advanced standing programs through the CAAPID 2015 cycle. I graduated a long time back 🙂 and getting a LOR from the dean of my dental school does not make sense. I am not aware who the Dean is right now and I am sure he will not know me. It is certainly not going to be a strong LOR. I have a post graduate degree in Oral and maxillo-facial surgery and have worked for several years. Getting a LOR from the chair of the department where I worked seems to make better sense as he is aware of my skills and other qualities. How do I get the schools to agree to a letter from my supervisor rather than the Dean of the school I left almost twenty years back? Any suggestions?
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