How would you respond if you were forwarded an email by your secretary that clearly wasn't meant for you? I'm an undergraduate senior seeking to continue on into academia, and one of the avenues I'm pursuing to accomplish this is through an NSF GRFP proposal. I spent well over a hundred hours agonizing over every word of this, and I'm happy to have three professors that I've done research with who agreed to write my letter of recs. 

The deadline for these letters is just a week away, and over the course of the past three weeks, one of my professors stopped responding to my emails, as he is prone to do on occasion when he gets busy. In the past, I had a negative experience where a careless professor forgot to submit a letter on time and this led to my sophomore study abroad proposal being returned without review. In this context, I sent the following email to his secretary (names redacted):


  Hi [Secretary],
  
  I wanted to inquire about an issue I'm having with Prof. [professor]
  at the moment. I asked him a number of weeks ago to write me a letter
  of recommendation for my NSF proposal (due November 2nd), to which he
  kindly agreed. He asked me for various things, including my transcript
  and statement of purpose, which I provided. Unfortunately, since then,
  I haven't been able to contact him in any way. I've sent him three
  emails over the past two weeks with no response. It is extremely
  important to me that this letter actually gets sent in; to put it
  bluntly, it's my future that's on the line here. I have in the past
  encountered the terrible experience of having a professor miss a
  similarly non-negotiable deadline, and I suffered from the loss of
  that opportunity as a result. I would greatly appreciate it if you
  could gently remind him of the deadline and ask him to confirm that he
  did indeed receive all of the application materials I sent him. If he
  needs anything else from me, I am more than happy to send it to him.
  
  Thank you very much,
  
  [Me]


Of course, the first thing she does is forwards this email directly to my professor, even though it was never written with his eyes in mind. I'm now worried that my professor (with whom I otherwise have a good relationship) will think less of me and write a poorer letter of rec on my behalf. I was wondering how academics would feel if they were put in a similar spot, and if I ought to be proactive in rectifying the situation, or if I should just let sleeping dogs lie. 

A Socially Anxious Student
My first question is what you thought would happen? In my experience, many secretaries would handle it exactly in this way - your email is fairly unspecific in what you thought the secretary would do ("remind him about this" - he/she did by forwarding your mail, and at the same time probably wondering why you did not send it directly to him). If you thought that the secretary would take responsibility for hunting down the recommendation letter for you, I think this is an unreasonable assumption. The secretary is the professor's assistant, not yours. In the olden times this may have included managing the professor's work backlog, but nowadays most people prefer doing this themselves and just having the secretary arrange meetings etc.


  even though it was never written with his eyes in mind.


Tip for the future: never write something to staff where you would be embarrassed if the boss saw it, especially if you don't know the person well. However, I see little in this email that would offend me, other than maybe the implication that you thought I could not be approached directly about this. But of course other people get offended by other things.


  I was wondering how academics would feel if they were put in a similar spot, and if I ought to be proactive in rectifying the situation, or if I should just let sleeping dogs lie.


I am for "letting sleeping dogs lie". Very likely there really isn't a situation to address, and if there is you can still tackle it once it comes up.