EARLY! I asked people during my rotation — if I connected well with someone during my sub-I, I’d make sure to ask them at the end of your rotation so they have plenty of time to prepare. Also - if you aren’t applying for months, having the conversation in person makes it way smoother when you email/call in the future. The worst situation you can have is to ask late and have your application be delayed because of this.
You should always ask your recommender for a letter of recommendation at least 2 months in advance. Professors and physicians can have extremely busy schedules, so it is best to respect their time by asking months in advance. Don't forget to send them your CV or resume, so they can highlight how great of a student you are!
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