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I sent a reminder email one day before the due date for a couple of my applications to grad school. It said something along the lines of

This is just a reminder that first due dates are tomorrow: [list of a couple of schools]. Hope you aren't too busy to write still. If you haven't received an email from these schools on instructions let me know.

I also sent "resends" to this professor's email via the schools' application portals. The professor responded with something like

You've already sent a list of deadlines [I did, but this was about a month ago]. It is NOT helpful to send repeated reminders.

I thought it was standard to send reminders before deadlines, especially if due dates are tomorrow with no letter sent. I feel that I have said or done something wrong. How can I prevent this from happening in the future?

I am now not only reluctant to send reminders for January schools, but I am now worried about the strength of this professor's letter. I have four letter writers, and I am tempted to drop his letter on some January schools. The reason for this is that this is not the only time he has been a bit snappy with me, although never like this. But I did tell him a while ago that I did not want his letter if it would not be strong, and yet he still agreed to write for me. So assuming he is honest about that, I feel I should maybe keep his letter.

This is all a little confusing and stressful. Thanks for your time to read.

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    One way to make your message seem less micromanaging and more proactive, is to ask if there is anything that your letter writer might need from you, or if there is anything you can do. This is a gentle way of saying "It's getting close to the deadline, and I realize that you are busy, so I'm just letting you know that I am happy to help you in any way that I can because I really appreciate your willingness to help me." This way shows that you are paying attention to detail, wanting to make the process as easy for them as possible, but still respectful of doing things their way. – iwantmyphd Dec 15 '17 at 4:08
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    It is not helpful to send repeated reminders. — Oh, yes, it is. – JeffE Dec 15 '17 at 12:00
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    I wouldn't describe that as "snapping." Mild annoyance at worst. – jpmc26 Dec 16 '17 at 1:53
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    This isn't a real problem, forget about it, nothing to worry about. Noone knows if he 'snapped', that's your inference. It looks polite to me. Presumably he is being bugged by other candidates too. Certainly he didn't go full Robert de Niro or Joe Pesci. It is good that he is organized enough to not need a reminder. So stop worrying and no need to stress. (If you really wanted, if you decided to send this sort of reminder in future you could say "Apologies if this reminder is unnecessary and I appreciate your current mail volume must be high, but here's a reminder that...") – smci Dec 16 '17 at 9:04
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    Here is what I did when I needed letters. When someone agreed to write me a reference letter, I immediately asked explicitly "The deadline is in such and such, should I send you reminders every so often?", on one occasion, the answer was "daily reminders, please" and on another "if you haven't heard from me in two weeks, please remind me". This way you can know in advance whether or not you even need to remind people, and how often. – Ink blot Dec 16 '17 at 12:19
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I feel that I have said or done something wrong. How can I prevent this from happening in the future?

The only odd thing you did was remind via both the online system and the personal email without acknowledging you did so in the email ("I am writing you an email on top of the online notices because I was told those sometimes get caught in spam.")

You could follow up with: "My apologies. I wanted to put the links at the top of your inbox so you could find them easily. I thought I should follow up with an email because I was told these can sometimes go to spam. I realize now this could be a bit obnoxious. Thanks again for your willingness to write a letter." You might stop by later and find out if he doesn't want ANY reminders or if he just wants a single one from the online system or a single one via personal email.

I am now worried about the strength of this professor's letter. I have four letter writers, and I am tempted to drop his letter on some January schools.

I would say you need to figure out if his behavior with you is just his typical behavior, or if he acts more negatively toward you than toward other students in your position. It seems most relevant to figure out your position relative to HIS baseline, not relative to a "nice person."

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    To emphasize this last part of the answer more: interpersonal skills are about calibration - both tuning your behavior to what works best with that person specifically, and also tuning your interpretation of that person's actions to take into account how that person normally thinks/acts/behaves. – mtraceur Dec 15 '17 at 7:33
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How can I prevent this from happening in the future?

Well, you can always go live on a desert island, or join an order of silent monks (and even living among monks would not guarantee that you will escape such foibles of human nature).

More seriously: you can’t prevent it, and you shouldn’t try either. You did absolutely nothing wrong by sending a reminder email. For every professor who responds irritably to your emails there are at least ten others who would appreciate your reminder email, and for some of them the reminder would even be needed to get them to upload their letter. Thus, you stand to lose much more than you will gain by changing your behavior because of the professor’s response. Just accept that working with other people necessitates occasionally having some strange and perhaps unpleasant interactions (trust me, you will have many more), and move on.

By the way, I also think it’s highly unlikely that the professor will modify his recommendation because of your email — that would be an extremely unprofessional and unethical thing to do, much more so than replying irritably to an email. Anyway, good luck with your applications.

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    This was my thought exactly - right now is just a busy time for professors (and everyone, really) so he's probably irritated at other things and this was just a small piece of steam to vent. – corsiKa Dec 15 '17 at 0:20
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    "Professors are human" strikes again. – gerrit Dec 15 '17 at 11:37
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    Joining that order of silent monks might, in fact, expose you to certain other "foibles of human nature"... – Jean-François Corbett Dec 15 '17 at 22:12
  • @gerrit: "Professors are socially inept humans" perhaps :) – Lightness Races in Orbit Dec 17 '17 at 15:55
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This is just a reminder that first due dates are tomorrow: [list of a couple of schools]. Hope you have time to write still. If you haven't received an email from these schools on instructions let me know.

This wasn't worded very well. By explicitly declaring your message a "reminder", you've:

  1. Taken a role in managing their activities.

  2. Suggested that you have less than perfect confidence in their reliability.

In general, both of these things might inspire offense. The primary issue is that, as a student requesting a recommendation letter, you're making a request of a professional-superior; deference and thanks are the typical expectations.

So, you'd have two ways to approach this: either as a professional-peer trying to coordinate an activity or a professional-subordinate requesting guidance from a superior.

To word something like this as a professional-peer:

I'm working on finalizing my applications to [list of schools] that have their deadlines tomorrow, so I just wanted to touch base with you on the recommendation letters and thank you again for your time and consideration. Please let me know if they failed to send you the invitation via email or if there's anything else that I could do on my end.

To word something like this as a professional-subordinate:

Thank you for helping me with the application process with your recommendation. Since a few of the deadlines are tomorrow, I'm trying to make sure that I got everything in order, including ensuring that I properly provided those kind enough to provide recommendation letters with access to the applications. Please let me know if there's anything else that I need to do, and thank you for your time and consideration!

Whether you approach a recommendation-writer as a peer or subordinate will depend on a lot of personal factors, so that's a case-by-case thing.

Stuff to avoid:

  1. "Reminding" them. Reminding someone suggests that you're not 100% confident that they were on-track. However plausible or reasonable this might be, some might still take offense to it.

  2. Managing their activities. In some sense, they've agreed to do something for you, and thus you might reasonably argue that they're obligated to perform the agreed-upon service. And while this might seem technically true, it'll often rub people the wrong way; it's best to avoid sounding like a micro-manager.

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    @Fred Definitely. And just to mention it, the objective tone that you'd used would work with a lot of folks, so I guess that it's a situational thing. – Nat Dec 14 '17 at 18:25
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    I suppose it's a matter of taste and/or culture, but (as someone who has written letters for students) I find OP's message direct and to-the-point, and I find yours sycophantic and insincere. No matter how it's phrased, it IS a reminder, so I see no point in avoiding the word. – user37208 Dec 14 '17 at 20:26
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    @Nat Less so, but they both come across a bit passive-aggressive to me, because they dance around the actual message being conveyed. – user37208 Dec 14 '17 at 21:08
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    I completely agree with @user37208 that your suggested letters come across as sycophantic and insincere. Also, Please let me know if there's anything else that I need to do just makes things worse by burdening the letter-writer with another (completely pointless and made-up) task that should not be their responsibility. As a letter-writer myself, I absolutely want the student to give me instructions (as clear and direct as possible) about what they need me to do, and conversely would be greatly annoyed if the student were to ask me to give them instructions, which is totally not my job. – Dan Romik Dec 14 '17 at 23:57
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    @DanRomik: That's totally not how I read Nat's suggested phrasing, but you've got a point that it could be read that way. Maybe something like Please let me know if I've neglected to provide any relevant information, or if there's anything else I can do that would be helpful to you would be better? – Ilmari Karonen Dec 15 '17 at 21:21
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My wife has a saying: "Everyone has their own bucket of [fecal matter]".

It's easy to take this at face value and react. If you've got experience with this person and he's always an obnoxious turd, that's one thing; on the other hand, if he's not normally like this, he might have been having a bad day and lashed out. Can you communicate with him directly? Consider dropping by for a cup of coffee, see if you can find out if he's having personal issues, talk to him directly and see what the issue really is. Remember, email truly sucks as a communication device for anything other than cold, dry facts.

If he's just not going to put in the work, and he lets you down, you will know better than to depend on him next time.

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    This is a great idea. My anxiety is at peak lately and it's tough to think things like this through. Good advice, thanks. – Fred Dec 14 '17 at 17:47
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    see if you can find out if he's having personal issues - I am not really sure if that is what students are supposed to do. – Rhinocerotidae Dec 16 '17 at 10:44
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One trick we had back in the day for exactly this situation was (a benign abuse of):

The thank-you note.

Instead of a reminder, which, as you have experienced firsthand, can be interpreted as pushy, send a note expressing your gratitude the professor for having written the letter on your behalf despite the "short deadline of X", and how much that means to you. Written properly, such a note can't be construed as inappropriately pushy.

If they have written the letter, they will get a warm fuzzy feeling.

If they haven't, then unless they're sociopathic (in which case you probably don't want their letter anyway), they will get some serious cognitive dissonance at not having written or sent it yet, and then most likely proceed to do so immediately. After which they will get the warm fuzzy feeling.

Everybody wins.

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    As with the other approaches advocating dishonest (if well-intentioned) methods, the expected “warm fuzzy feeling” could well turn out instead to be annoyance and resentment on the professor’s part at being manipulated and lied to, however “benignly”. Sorry, I simply don’t buy your claim that “written properly, such a note can’t be construed as inappropriately pushy”; for me, the best warm fuzzy feelings I get is when people are being honest with me rather than trying to manipulate me in a cheap, transparent way as if I was some kind of marionette on a string. – Dan Romik Dec 16 '17 at 0:37
  • @DanRomik I disagree. I think your use of the word "dishonest" is pushing its definition to its literal extreme, where it in fact turns into the concept of "politeness", which is, if one insists on interpreting things in a negative light, indeed a form of dishonesty. – Jean-François Corbett Dec 17 '17 at 15:04
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Just apologize and move on. No need to skip his letter. It sounds like you're moving on soon enough and won't have to deal with his snippy personality much more.

Some professors have asked me to send them reminders because they're busy, and so I do. You're not really in the wrong having done this, unless he explicitly asked you not to. Apologizing costs nothing and just greases the wheels. Sounds like this professor does a good job of staying organized (or thinks he does). Some professors get hundreds of emails a day, and he was probably annoyed at one more (two more?) email(s) telling him something he already knew.

Now the question is whether you send the apology by email ...

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    Maybe an apology isn't needed at all. The professor might be in over his head with writing too many letters too close to the deadline and snapped due to stress. Maybe the professor just needs a bit of quiet to get the letters done. We all snap sometimes, hopefully we snap at people we can make it up to and who can forgive us. – Bent Dec 14 '17 at 19:57
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    @Bent An apology is an expression of forgiveness? – Azor Ahai Dec 14 '17 at 20:01
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    The professor should perhaps apologize at a later stage, not the OP. I wouldn't apologize to the professor, nor would I mention anything as long as the letters gets send on time. OP should not apologize, if in OP's situation I would forgive the professor as long as the letters are sent. In the western world if you apologize you are the one that needs to be forgiven. This is the other way round. – Bent Dec 14 '17 at 22:25
  • @Bent Respectfully, I disagree. The OP bothered their professor by sending them an extra email. Sometimes you have to swallow your pride (did the professor overreact? yeah, a little bit) and smooth things over by taking the high road and apologizing for upsetting someone. In a perfect world, yes, the professor would apologize for snapping. But this isn't a perfect world. – Azor Ahai Dec 14 '17 at 22:32
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    I think the question is not so much whether the student has a moral imperative to apologize (it sounds like you agree that he doesn’t, since he didn’t do anything wrong), but whether it would be strategically beneficial for him to apologize. On that question, I would argue that when someone snaps at you irritably for sending him too many emails, the last thing you would want to do is to bother him with yet another email apologizing for all the previous emails... – Dan Romik Dec 15 '17 at 1:25

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