Balancing empathy and deferring to the syllabus in teaching responsibilities

It sounds to me like you are allowing yourself to be emotionally manipulated by your students, particularly the one (who sounds super obnoxious) who told you about the promise for a luxury car from their parents. It’s indeed important to have empathy, and I find your conscious insistence on practicing empathy every day incredibly noble and admirable — if only more people did that the world would be a better place — but at the same time, sometimes a person has a job to do and needs to put the larger interests of the mission he or she serves ahead of the emotional need to “be nice”. Indeed, being nice to people who are undeserving is often harmful to those people. You would not be doing any favors to the immature, manipulative student who wants to get a luxury car by giving them unfairly favorable treatment out of pity or “empathy”. (The student with medical problems is a completely different story, where the request sounds a lot more reasonable.)

In any case, empathy is about how you relate to people and not about the decision you make on their petition. Even on occasions when I’ve had to turn down a desperate student’s request for a grade change, and knowing that that’s the only decision I could possibly make in good conscience, I would like to think that I explained my decision to the crying student with empathy - I certainly tried my best, even if the students in that moment sometimes only seemed to care about having their request denied and might well have thought me to be a cruel, heartless person.

So what is a good way in practice to solve the dilemma? The answer you quoted in your post has it exactly right. You give an extension to the people who have a legitimate reason to need it, and refuse it to those who don’t. That’s all there is to it. “But what is 'legitimate'?” Exactly what you judge to be legitimate — after first pausing to take ten deep breaths, counting down to zero from one hundred, writing an email draft answering the request and saving it in your drafts folder, going on a walk or a coffee break, and finally coming back and looking at the question with fresh eyes. If at that point you still think the need is legitimate and can say with certainty, or least with reasonable confidence, that you are not falling victim to emotional manipulation from an unscrupulous student, by all means grant the request.

And whether or not you‘ve decided to grant the request at that point, be content to know that you have been true to your principles of practicing empathy, and that you are doing your small part to help make the world a better place.

You talk about empathy towards those asking for extensions, what about those who didn’t?

Many students work their butt off to make deadlines and never think of asking for an extension. By granting extensions to some students who don’t have a valid reason (in my book that’d be medical or death/severe illness of human loved one, but your policy can differ), you’re basically telling those silent hard working ones that their time is worth less than that of others. That’s not empathy in my opinion.

In fact, this is exactly what I tell students who ask for extensions: I can’t grant you one because it’s unfair to other students taking the class. They usually understand where I’m coming from and take it better than outright refusal.

EDIT: perhaps to drive the point home here - you may be inadvertently discriminating against students who feel less empowered in a university setting. Unfortunately, these students often enough tend to be from certain socioeconomic/minority/gender groups - think about the potential implications of this practice!

My thinking on this issue has changed dramatically over the years, and I now give extensions much more frequently than I used to. (I'm not saying this is necessarily the right course of action, though.)

I would advise you to consider some guiding principles at play here:

1) Consider the reason that there's a deadline in the first place, and ponder the possible harm done if it is violated. To be clear, this is not a rhetorical point. As an undergrad, I had a course where all homework assignments were due in the last week of class; suffice it to say that the three weeks leading up to that were not fun for me. Deadlines are good, because they require students to maintain pace with the course and avoid a huge backlog at the end; additionally, work in a class is often iterative, and in those cases it's imperative to stay on top of it.

Here are some examples of what I'd regard to be very good reasons to keep a hard deadline in place without extension:

• You need to post a key for the benefit of the rest of the students, which would render the assignment pointless for a student completing the work late.
• The work represents some fundamental concept that will be built upon in class, and it's genuinely important that the student have the work completed on a particular schedule.
• You're planning to grade the assignments right after they're turned in, and it may take you more time overall to extend the assignment -- either because you need to get yourself back into a grading mindset somehow, or you have to reopen something on your computer, or whatever else. Your own time is valuable, and it's well within your right to fight for it. But this logic ought to apply to everyone. If this is your reason, I'd advise you to drop the lowest X homeworks or have some similar policy that allows some flexibility for truly exigent circumstances, and to apply the policy uniformly to all students.

Personally, I find it often the case that there is no pressing reason to keep a specific hard deadline in practice, but rather that the general concept of deadlines should be maintained so students don't fall far behind. For that reason, I tend to freely give extensions. When a student asks for several, I have a conversation with them about it.

2) It is probably better that students complete homework late than that they don't complete it at all. Of course, this must be weighed against your responses to 1) above. Like I said, there are very good reasons to be strict about deadlines, and those reasons may well win the argument.

3) Remember that if all that's needed to get an extension is a good reason, it's very easy to lie about those reasons. If you adopt a policy in which "My grandmother died" is a good enough reason that warrants an extensions, and "I made a bad choice and binge watched Game of Thrones" isn't, then you're implicitly putting yourself on the hook for documentation of the good reasons. In the long run, if you differentiate between reasons but don't demand documentation, you are likely to develop a reputation that will result in some students who binge-watched Game of Thrones instead reporting to you that their grandmother died. And in fact, in this scenario, the only students who won't receive an untoward benefit are precisely the ones who compelled to be honest about their reason. That seems bad.

4) Make a choice that you'd be willing to defend to a supervisor. If you're going to treat students differently, imagine sitting in a room with both of them and an administrator and justifying your decision. If you can't easily do that, you're probably making a mistake. And if you're unsure what you could defend to a supervisor, then go find a supervisor and talk to them about the situation immediately.

5) When unsure, defer to empathy in all cases. I know that you're trying to do that here, and I think your heart is in the right place. Empathy is helpful for so many reasons; it's beneficial to the students' education, it's easy to defend politically, and you'll probably sleep better at night. If a student is irresponsible or taking some sort of shortcut, you're very likely to detect that in other places (such as tests). Going out of your way to enforce various "good behaviors" (such as deadlines) is, in my experience, an unsustainable career choice.

Final thought: I have never once regretted giving a student leeway, but I've regretted behaving strictly.