does it look bad to send emails late at night?

A reader writes:

Does it look bad to send/respond to an email late at night? I am generally forgetful, and the smaller a task the more likely I am to forget about it until later that evening. Randomly, at 10 p.m. I will remember, “Oh shoot, I didn’t tell Jane that Wednesday doesn’t work for that meeting and Thursday would be better.” How bad is it to send these emails after hours? Am I overthinking it, or will it look put people off to see emails that are time stamped at 10:30 p.m.?

I answer this question — and three others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

  • How to cancel an interview with a rude job applicant
  • Should I let a client know I’m struggling with mental health issues?
  • Is it bad to step back from a management job to a less senior position?

{ 136 comments… read them below }

  1. Essentially Cheesy*

    Even just based on the question .. and also my own experience. Yes, it does look bad.

    One boss had insomnia and would answer emails at about 2 a.m. His boss would come to be and say “what is the deal with him?!?” All I could do was shrug my shoulders.

    I would say this applies to email replies after even 6 or 8 p.m. but it may depend on office culture.

    1. AA Baby Boomer*

      Use the delay delivery feature in Outlook. I have done the same thing. Something popped up in my head hours after I got home. Set it up to go out when your normal work hour starts; or 10 – 15 minutes later. Outlook has to be open for this to work. I come in at 8am; I’ll set them to go out around 8:05, 8:10, etc. The receipant will not know you used that feature.

      It gives them the impression that you expect them to work at night. And that you are available at night; they will feel free to call & email after hours and expect a response from you that evening; versus the following morning.

      1. Siobahn*

        “It gives them the impression that you expect them to work at night.”

        Not everyone. I manage a team of 5, and they know that if the see an email from me before or after work hours, they’re not obligated to respond, and, more importantly, I’d rather them not (and I have shared with them the couple of reasons why I might e-mail at off hours). It’s the same with me and my boss.

        1. Spencer Hastings*

          At most, they are probably thinking “she’s the boss, that’s why she gets paid the big bucks!”

          (That’s my logic, anyway — I’ll be acting my wage, and I’ll change what I’m doing only *after* there’s an explicit “we’d like to promote you to X title, and here’s what that would mean in terms of increased responsibilities” conversation.)

          1. Phryne*

            Yep. I have coworkers and managers that sometimes mail late at night. I consider this wholly a them-problem and not a me-problem.

        2. ferrina*

          You have to be really clear with them if this is the case. I was extremely direct with my team that I expected them to be responsive from 10-5, and any time outside of that, they weren’t expected to respond to email or IMs (unless I had specifically told them to be responsive- for certain projects it was sometimes necessary). I explicitly said that they may see odd emails/IMs from me outside of business hours, but that I absolutely did not expect it of them, that I was flexing time, and that that was part of my job as Boss. A couple times I gently scolded teammates for working late on non-urgent things.

          You have to be really consistent about this. I’ve had bosses say “oh, you don’t need to respond outside core hours” then get upset when I didn’t have a report ready at 9am (because they’d asked for it at 7pm). Even well-meaning bosses can slip up on this.

          1. Siobhan*

            But I have been very clear with my team. So has my boss with me. We don’t have a problem with this, so I am uncertain of your point relative to my post.

            My response was to the generalizing that “It gives them the impression…” Some teams, like mine, won’t have a problem. Other groups of people, which I can’t speak to because I’m not a member, might have a problem. Individual bosses, like yours, might stray from things, but mine doesn’t.

      2. sam*

        The problem with the delay delivery feature is that when it sends, it is still timestamped with the time you *wrote* it rather than the time it was sent, which, if someone is opening their inbox in the morning, it will still look like you sent it at 2am, so it doesn’t really solve the specific problem of “why is this person sending emails in the middle of the night”.

        What I do instead is save the message in my drafts folder, and then add a reminder for, like, 8am so that I can go in and actually send it then. Added bonus is that it gives me another fresh chance to proofread it.

        1. Ginger Baker*

          I just tested this in Outlook – my delayed email shows the time stamp as the time sent (not the time drafted) so safe for use in this. (To the best of my knowledge it generally works this way – but, I highly recommend testing in an email to yourself to confirm your system works as expected before using this as a standard practice!)

        2. Avril Ludgateaux*

          The problem with the delay delivery feature is that when it sends, it is still timestamped with the time you *wrote* it rather than the time it was sent, which, if someone is opening their inbox in the morning, it will still look like you sent it at 2am, so it doesn’t really solve the specific problem of “why is this person sending emails in the middle of the night”.

          This has not been my experience using Outlook, but perhaps different email clients have different rules? Mine shows the time it arrived in the inbox.

          1. Kacihall*

            I can confirm that Gsuite shows it s the time actually sent. I do a lot of work on weekends but refuse to let my customers know that. I will work overtime, but only on non customer facing stuff. in July and August I get a TON of overtime, which is great for Christmas money, but if I give the impression to a client that I can work late at night or on the weekends they will get annoyed that I don’t ALWAYS reply to them on the weekends. My manager is salary and regularly works on the weekends – in part because she’s let clients know she works then, so they ask her for time sensitive things over the weekend.

          2. Kewlm0m*

            My Outlook also shows the time the email was written, so I save my late emails as drafts and send them the next morning.

          3. nobadcats*

            I use Outlook through the browser rather than the app. I just checked a couple of emails that I sent last week at 3.37ish am* and set to arrive by 8am. They all appear to have been sent at 8am.

            So it might be the difference between the browser and the app. Or if you do use the app, between mac/pc or an android tablet/ipad.

            *insomnia’s so much fun, might as well get the deadline done ahead of time

      3. Essentially Cheesy*

        No thank you, I’m all for setting boundaries for working hours but thanks for the information.

      4. Avril Ludgateaux*

        Echoing Delay Delivery – but be careful, it can glitch out and get stuck in your Outbox and never send! I was relying on Delay Delivery to enforce work life balance over the pandemic (mostly to signal that off-hours e-mails will get a response during my normal hours, so people didn’t get in a habit of expecting evening or midnight responses, even though I could not resist writing up the response on the spot), and it worked perfectly… Until it didn’t! I don’t know if our IT or e-mail provider or VPN or whoever changed some permissions, but now, whenever I “delay delivery” in the desktop app, it gets stuck in the Outbox. (I myself made no changes to my computer or program settings.)

        Yes I have Googled it and tried trouble shooting (like turning off the local cache). All it did was cause more problems! At least web-hosted email is reliable, so when I need to schedule delivery and won’t be able to monitor the Outbox (like if I will be OOO), I use that.

        1. MigraineMonth*

          I have all my emails scheduled with a two-minute send delay (because it usually takes me one minute to realize I forgot an attachment), and two times in the last 3 years it has gotten stuck in “outbox” for no reason I can determine.

          1. AnonInCanada*

            And even worse is that that email stuck in the outbox will result in every other subsequent email you send getting stuck behind it as well. Oh what fun it is to get it unstuck!

        2. Orange You Glad*

          This is my experience with the delay delivery in outlook. I set up it but it doesn’t actually send until I open Outlook the next time. So if I write an email Sunday night that is scheduled for Monday morning but I don’t log in to my computer until Monday afternoon, the scheduled email doesn’t go until Monday afternoon. A little annoying when I’m trying to get ahead of work for a period that I’ll be out.

        3. Michelle Smith*

          Yes, delay delivery in Outlook has literally never worked for me and only caused emails to get stuck in the Outbox. Much better for me to put a calendar notification at 9 am or whenever that says “Email Jane” instead of trying to send an email that will never reach the recipient. Plus then I don’t have to keep the work laptop on.

      5. Venus*

        I don’t schedule them because my solution seems much easier. If I write late emails then I leave them open and send them off the next morning.

      6. Green great dragon*

        The downside (with my Outlook at least) is that it doesn’t send until you launch the programme in the morning. This may not matter, but it may mean someone else has to work without full information for a couple of hours or more (start times with us are anywhere between 7 and 10am), or that your email appears after the conversation’s gone in a completely different direction and confuses everyone.

        I’ve seen people with email signatures saying something like “I email when it’s convenient for me, I don’t expect a reply outside your working hours”

        1. OtterB*

          One of my colleagues, who is on the opposite coast from most of us, has this in his sig. Something about realizing his working hours may not match yours, so if you receive this email outside your normal hours, feel free to respond during your working hours.

      7. Khatul Madame*

        Be aware that Delay delivery option in Outlook only works on email messages, not meeting invites.

      8. Delay Delivery's BFF*

        Delay delivery is my best friend as someone who constantly reads emails at strange hours of the night. As for the time, I usually choose a time that makes it look like I replied just then (10:37, 9:23, 9:51, etc.)

    2. londonedit*

      Yeah, I think a lot of it has to do with office culture. I don’t check work email outside of my working hours, so I don’t pay a lot of attention to the time stamps on the emails when they land in my inbox in the morning. It’s also extremely unusual for my boss to email me outside of working hours (and even if they did, they’d never expect me to respond at that time) so if I logged on and saw they’d sent me an email at 10:30pm, I’d probably ask them what on earth happened to make them work so late. But that’s our specific situation – in other office cultures and industries people emailing at all hours of the day and night might just be something that happens.

      1. Anonymous 75*

        I don’t think I’ve ever looked at a time stamp on an email unless I deliberately needed it.

        1. UKDancer*

          Yes I don’t think I have either. I check my emails in the morning and deal with what’s come in since I logged off. I don’t really look at when things are sent.

          1. allathian*

            Yeah, me too. That said, even if I did, I wouldn’t even notice unless it was the middle of the night. We have set core hours between 9 and 3, and if we’re absent during that period, we’re expected to mark it as an OOO on our calendars, which are visible to everyone in the organization. Other than that, it’s very flexible, we’re just expected to attend the meetings we’ve agreed to attend, but some people love to work on things that don’t require synchronous collaboration with others after 10 pm, and send emails after that, and that’s fine as long as they don’t expect an immediate response from people who work a more traditional schedule.

    3. Goldenrod*

      “Yes, it does look bad.”

      Agreed! I had a manager once whom I actually liked quite a bit, but she was chaotic and flailing, and worked at random hours. She staggered in late most days, and would often send emails at 2 or 3 in the morning.

      I think she thought it made her look industrious, but it actually made a bad impression. It just added to the general impression that she was chaotic and disorganized. Which she was! But she didn’t need to ADD to this impression.

      Agree with the suggestion to use the delay feature! Either that, or just save it as a draft and send first thing in the morning.

      1. ferrina*

        I had a manager like this. You were more likely to get an email from him at 2am than at 2pm. He was also notoriously bad at his job and would frequently let things fall through the cracks (He was also head of finance. so…..not good)

    4. T.N.H.*

      I schedule emails every day. You can do this almost as easily as you can click the send button. Do not send emails after hours if it’s not normally part of your role.

    5. Meep*

      The owner of the company once messaged me a question at 11:00 PM at night. At 5:00 AM, he figured it out. Because he told me with a “NVM” text. I was asleep the whole time.

    6. Girasol*

      I used to do this when I couldn’t sleep expecting that my messages would be read when people came to work in the morning. All the contract staff replied within 5 minutes, even at 2:00 am. I quit doing that!

    7. NotAnotherManager!*

      It’s entirely office culture dependent. Not responding to an email between 6 and 8 PM ET would be more frowned upon in my office than sending one. I just had to mediate an issue last week where someone sent an email at nearly 10 PM and was upset that no one took care of the issue until the following day and I had to remind them that, after 9 PM, we call with emergency needs, not email.

      We also have people who work shifted schedules around their family obligations, so not everyone is on a 9 AM – 5 PM shift, not to mention the people spread across time zones.

  2. Flak Jacket*

    +1 on scheduling emails for the following morning. Not only does it establish boundaries and expectations about when you are available, it eases any burden on staff who might be worried about setting boundaries and expectations.

    1. Single Parent Barbie*

      +1+ I do it with text, emails and slack messages. My work counterpart and I work very hard to make sure the other keeps work/life balance. So he hates when I message or email when I am off (BUT THATS WHEN I REMEMBER IT). So unless its an immediate thing, I schedule it to go out during my work hours.

  3. Your Computer Guy*

    If you’re using Outlook, there is an option to schedule the email to send at a later time. So you can draft your emails at whatever odd hours you want, and then schedule them to be sent at the start of reasonable working hours.
    If you’re using the desktop app, it’s under the Options tab, “Delay Delivery”. In Outlook on the web, hit the down arrow next to Send and there should be a “Schedule send” option. Gmail has a similar function to Outlook on the web.

    1. NotAnotherManager!*

      The one caveat to using Outlook for this is that the machine running Outlook (unless, I guess, you’re using OWA) has to be on, connected to the internet, with Outlook running because Outlook holds the copy in your “outbox” rather than on the server queue. I scheduled a non-urgent email recently because a colleague was on vacation, and I didn’t want it to hit her while she was out, but my laptop took it’s own sick/personal day and the message didn’t go out until the Help Desk fixed it a day later. I use scheduling all the time, but you also have to be aware of its limitations.

      1. Mid*

        Yeah, I learned that the hard way when I ended up with a ton of emails stuck in my outbox instead of sending. It seemed it happen after we had an update, because I didn’t change how I scheduled emails. But it seems like if I’m not actively online when the time to send happens, it’ll stick in my outbox and not automatically send. So double check always!

      2. Avril Ludgateaux*

        Good advice, but Outlook (desktop version) is buggy. Some months ago, my Delay Delivery decided to stop working. I hadn’t changed any settings, although I can’t guarantee my employer didn’t push out some feature crippling rule. I thought it was what you wrote – that it was because I put my computer to sleep overnight and maybe it was disconnecting from the internet – so I tested it with a scheduled e-mail to myself while I was actively on the computer, using the internet, monitoring my Outbox. Still stuck/never sent.

        Ever since, things get stuck in my Outbox perpetually, no matter what I do, if I try to use “Delay Delivery” on the desktop program.

        Thankfully, Office 365 and Outlook’s web client exist and schedule delivery through that avenue is reliable. When I need to send something at a time other than immediately, I end up using the web client!

      3. Helewise*

        Yes, and the delay feature – at least for me – appears to be local. So if I’m working from our VPN and delay a message, I need to open Outlook in the VPN in the morning for it to send. It’ll just stay in the Outbox if I’m working from the desktop the next day.

    2. neeko*

      This is what I do as well. It’s super helpful especially with people I manage so they don’t think I’m expecting them to respond after work hours.

  4. AlwhoisThatAl*

    It can be annoying as some people who hear the email come in, tend to look at it so it breaks their evening. Or it comes across as you working many hours trying to impress.
    As other people have said, the Email Scheduler is your friend

    1. neeko*

      To offset that, I set notifications to be only during my work hours. It’s helpful to curb that urge!

      1. Mel*

        How do you set notifications during working hours only? I’ve turned off e-mail notifications on my phone because I find them stressful after hours and on weekends. But I would like them on during the work day.

        1. leave me alone after 6*

          If you have an iPhone you can set “focus” times that will restrict certain apps during certain times- you can even remove apps from your home screen all together. This may be more difficult if your work/home email are from the same provider.

          So for example- from 7 AM to 6 PM M-F, I allow all work related notifications and restrict frivolous ones (yes calls and texts, no to promotions/updates). At 6 PM my phone switches to a new home screen sans teams/outlook, I see everything that was restricted during the day, and I don’t get any work related notifications until the next day.

        2. neeko*

          Depending on the phone and application you use, you can set them. Like for the Outlook app on the iPhone, if you hit the circle with most likely your first initial on the top left side – next to the word inbox, then hit the clock icon on the menu that opens up, you can set a “do not disturb” schedule.

        3. Alexander Graham Yell*

          My iPhone has a “Personal Time” setting that is separate from Do Not Disturb or Focus. I have it set so that from about 8pm – 9am on weeknights and all day on weekends I see no work-related notifications

        4. I have RBF*

          I set “do not disturb” times on my Android phone. I’ve set it so only known contacts can call me and have it ring, and that no application notifications will sound. I also set most applications in general to “No Notifications” or “Silent” because my phone constantly chiming interrupts my concentration.

          Aside: Why the heck do application and website programmers think that people want notifications all the time? Why do I constantly have to tell X random website that no, I don’t want “notifications” from them in my web browser? It’s like these apps and websites have an inflated opinion of their own importance. I don’t understand it.

        5. dryakumo*

          At least on Android, the Outlook app has a “Quiet Time” setting (under Notifications->Do not disturb) that you can also use to set for Teams. I have my quiet time set for 6pm-6am weekdays and all weekend. Highly recommend it!

  5. NorthernTeacher (just on sn adjusted path)*

    Just an interesting think to note. Here in Ontario, Canada a law was passed that employees have a legal right to not monitor their email outside of work hours. There has been an attempt by the local school board to encourage admin to schedule emails to send within the school day. It is a good thing, but it can be hard to check email once students arrive and some of the emails have sutpride same-day deadlines that would have been nice to see before the bell. Occasional forgetfulness is ok,but when it happens frequently it is a sign of poor organization.

    1. Mid*

      Are you saying that sending emails after hours is seen as a sign of poor organization in your area/field? That’s so interesting, and it’s fascinating how different work cultures evolve. (Because I’m in international BigLaw, so we have people working 24/7 and no one would notice if you sent an email at 2am.)

      1. learnedthehardway*

        Agreeing that it is industry-specific. Most of my clients know that I do a lot of work late at night – it’s my best working hours. I do a fair amount of outreach to potential contributors as well, and I’ll email late at night on that too. It’s part of the work I do, and it’s necessary for me. My days are occupied with other stuff.

        I’ve only ever had one person take offense to that, and they were massively problematic in a whole host of other ways, so I’m not going to stop doing it.

        I choose to work this way because I have flexibility with how and when I work.

      2. turquoisecow*

        yeah my husband works in tech, and with a lot of international people in all different time zones. he often will be working at 11:00PM to catch up, and will send and receive emails at those times and no one seems to blink an eye

        i work for a much smaller very local company and if i sent an email at 11PM I think my boss would pull me aside and ask me what i was doing working so late. The only times I get emails after hours are when my grandboss is working late and responding at night, but she’s extremely busy and in meetings most of the day so often doesn’t have time to read emails during the workday. but there’s no expectation that i reply at that time. I’m also not a manager or working on anything time sensitive; my husband is higher up the ladder than I am and sometimes (though not often) has actual emergencies that do need responses at night.

        it’s definitely work and culture dependent.

      3. NorthernTeacher (just on sn adjusted path)*

        Sorry. I was not clear because typing on a phone while multi-tasking.
        The disorganization was that the principal would know the deadline for days/week. But she would forget until about 5pm the day before and send a email. It would be waiting when I turned on my computer the next morning, so I could rearrange my plans as needed. But, nowthe emails arrive 15 minutes before the first bell when I am setting up the classroom..etc There are days when I don’t get back to the computer until after students have left. S
        Often they are small tasks, but there have been some big ones… like the deadline to submit student work for the yearbook moved 3 days early, due by 2nd recess and late work would not be accepted. Fortunately, staff have started warning each other when passing in the hallways with a “did you see _____”. That day I had to cancel a planned lesson, let the students have free time and scramble. Had I known before school, I would have finished this before the bell.
        The law says that employers can not except employees to be checking email out of hours. Therefore, it is ok to send the emails. Our principal has taken it further with delaying sending which is ok. I actually like it, because it helps me keep work/life boundaries….I don’t feel the need to check email before bed because I know nothing will be there. But, her disorganization resulting in surprise deadlines in delayed emails is the problem.

        1. NorthernTeacher (just on sn adjusted path)*

          sigh. *expect…not except
          The phone is great for reading, but the small keyboard on the screen sucks for typing.

  6. Clisby*

    I would have said no, there’s nothing wrong with sending emails late at night. I’m retired, but if I had gotten emails late at night, I’d never have seen them, because I didn’t check emails at night. I’d just figure that was when the sender found it convenient to hit “Send”.

    However, if you think other people are overthinking this, just do as others have recommended, and schedule the email to be sent later.

    1. MigraineMonth*

      Yeah, I don’t care when someone sent an email as long as they don’t get huffy if I don’t immediately respond.

    2. Elle*

      I don’t normally mind, but was fairly pissed off by the rather passive aggressive email sent to me by about the 4th most senior person in my (large!) organisation at 5.30 pm on a Sunday, especially as I received it on Monday morning shortly before receiving an all staff email, signed off BY HER emphasising that emails should not be sent outside standard business hours, even if you worked flex hours, and explaining how to use delay send!

      if it had been an email telling me what a good job I was doing, I might not have minded, but she basically accused me of lying about a situation, so it was more of an “and ANOTHER thing” moment!

      the other one I found very off-putting was the 3am email from a hiring manager acknowledging receipt of my documents – I thought it was a red flag about her and the job (I was correct – she later left that role dur to her cocaine addiction…)

  7. Bast*

    I think the email thing depends on your field. I work in BigLaw, and emails at random times are common, if not expected. I’ve been pushed to check and respond to email during off hours, and so far have been successful at NOT doing so, but others are not so lucky.

    1. Mid*

      Yeah I work at an international BigLaw firm, and so we have people working literally all hours of the day in different time zones. When I was at a small firm, I’d delay sending because everyone was in the same time zone and a 1am email would be weird.

      Now I rarely even notice email times, though I’ll still delay sending if it’s someone local to me, or if it’s something I don’t want a response to until the next day.

    2. Alexander Graham Yell*

      Yep – I’m in consulting and my bf is in law, and I’d say I have slightly better work/life balance in that I can turn off notifications at night. He’ll generally know when he might have a late email coming through and will warn me, but we’ve definitely had movie nights that were interrupted by an urgent 11pm text.

      My issue is the opposite, though – my clients are primarily in the US while I’m in Europe, so I have to remember not to send them things at what would look like 4am, but I have to be more responsive later in the evening to balance things out.

  8. Falling Diphthong*

    #3: I think disclosing a mental health issue like this often lands as an intimate thing you do only with people you trust, when you want their help in managing things. So doing it to a client could land as TMI and alarming, especially a new client.

    At one end of the scale, someone who knows you well, knows you normally do great work, knows that e.g. you’re in a caregiver role right now and it’s incredibly draining but temporary–they probably want to give you a chance to get back to normal. And even they may also give you less work, because deadlines matter for their work. At the other end of the scale, someone who knows you not at all except for this one project which was not executed well. If you ask for another chance to make a first impression, you usually need to sell that the poor performance was “because of this one-off circumstance which has been completely resolved” rather than “because of this ongoing problem I struggle with.”

  9. Clefairy*

    For #1, I think it’s highly dependant on your company culture. At my company, it’s frowned upon, and when I brought the habit from my last job, my boss ended up talking to me about perception. Now I try to keep my emails to regular business hours, but if I’m really itching to send something late, I just schedule it for the next morning at an odd time (like, (9:07am instead of 9:00am) to make it look like I send it during business hours.

  10. Medium Sized Manager*

    Co-signed on scheduling emails. I often choose to work on a Saturday morning to clean up my inbox before Monday, but I don’t want my team to think they should be mimicking the same. I also recommend varying the delivery time so they don’t get 7 emails at 8 AM on a Monday (the default for Gmail).

  11. Falling Diphthong*

    #1 I always find odd when it comes up, in that I work with teams where some people do 9-5 M-F and some evenings and some on some other schedule–people send out emails whenever it works in their day to send some emails. My spouse and oldest child work with international teams and if you had to send it for “the start of everyone else’s working hours” no emails would ever go out.

    I take Alison’s point about setting standards as a manager, but also the oft-repeated tales of email schedulers not quite working as anticipated and something never sent. While technically people are emailing at you, they’re working at 10 pm because they finally realized what is wrong with the Bigglestaff figures and while fixing that went through some emails and none of the timing is meant to send you a message other than the message “The Bigglestaff ruminant is a llama, not a cow.”

    1. IT project manager*

      Exactly! I am on pacific time and work with people in all time zones. Sometimes I will work late to get something out so the people who are the east coast have the info first thing in the morning when they start work rather than wait until I’m working which is mid to late morning their time.

      Then we may have clients and vendors in time zones all over the world. We all work in our own time zones and no one expects someone to reply immediately outside of their own normal hours to an email received late at night or early morning

      Delaying emails to only send during certain hours would just cause roadblocks and cause delays in projects as people wait for information and can’t move forward without it.

    2. Spencer Hastings*

      Yep, same. I’m in public accounting, where this time of year someone could theoretically be working at any hour of the day. (I work for a small firm, with most employees concentrated in a single geographic area, and there’s a tiny minority of people who are actually in other time zones.)

      This time of year, I tend to get in around 8 (our normal start time during the rest of the year) and leave late in the evening, but I know some other people who start working closer to 6 am and leave earlier. So it’s like we’re in different time zones, even though we’re physically in the same office.

      Under this type of circumstance, for the night owl to schedule-send would be actively counterproductive. Let’s say I have a question for “Emily”, and it’s 8 pm and she’s already gone:

      Option A: Spencer sends email at 8 pm. Emily sees it when she gets in at 6 am. Emily writes back. Spencer gets in at 8 am and sees the response.

      Option B: Spencer schedules the email to be sent in the morning and turns off her computer. Outlook sends the email when Spencer’s computer is next turned on at 8 am.

      Even if, in Option A, Emily doesn’t have time to respond within those two hours, I still think it’s *no worse* than Option B. (And potentially better, if it’s important for Emily to be aware of whatever issue I’ve brought up sooner rather than later.) And I think this is true no matter what the relative positions of each person in the hierarchy are.

    3. Parakeet*

      If not for this site, I would never have known that people interpret email times to the degree that some apparently do! If someone sent me email at an odd hour, I would assume that they structure their days differently than I do (or, depending on contextual factors, that they were in a different time zone). But then, it also didn’t occur to me that people were setting up their work email to show them notifications every time something new comes in. I can see why that would be a problem – but then, why not turn notifications off for the work email, or only log in through a webmail interface if you’re on your phone?

    4. Orange You Glad*


      If I couldn’t occasionally send an email when I’m working on a Saturday afternoon, I’ll probably forget all about it or think I sent it when I didn’t. I’ve tried scheduling emails it just doesn’t work properly in our system (for some reason our system will only send the held items after you have physically logged back into Outlook). We have employees in every US time zone so emails could be coming in really early or really late by nature.

      We do make it clear as part of our office culture that it is not expected to work or respond on weekends but there are a few positions that may take advantage of a quiet Saturday to get things done.

    5. amoeba*

      Yeah, even within the same time zone – my team works very different hours, with some people starting at 6 a.m. and some at 9. I’m firmly team 9, so if I was sending something late at night, that would mean it doesn’t go out until 3 h into other people’s workday. In addition, a lot of email that I send has recipients in multiple time zones, anyway.
      I can see doing that for non-urgent “standalone” mails, but as soon as it’s part of an email chain, I’d be super worried that other people would reply in the meantime, making my email obsolete and/or confusing.

    6. Shiny*

      I’m in international development and even though I’m on the donor side, which has a much more 9-5 culture than the implementing side, that’s 9-5 in my time zone (currently East Africa Time). I can’t imagine ever looking at a timestamp, as by definition, we get messages 24/7. When I was on the implementing side and working with global teams from the East Coast, I had to majorly pushback on some clueless types who wanted me to make all meetings in THEIR 9-5, and I did so by keeping my call availability times from 7 AM to 9 PM. It would be laughable for anyone in my industry to think about the timing of emails. Obviously, from this comments section, it’s a bigger deal in a lot of sectors!

  12. Qwerty*

    If you regularly send emails at night, just be open with your team that you tend to catch up on emails in the evening so there is no pressure to respond. Clue in your manager so they don’t think you are regularly working through the evening (both so they aren’t worried about you and so they don’t hold it as an example to other teammembers). It has become really common in my industry post-pandemic for people to be strict about leaving work on time to have dinner with their families and then sign on in the evening after the kids go to bed if there is something they forgot to wrap up.

    If you are also a manager – take extra care to make sure your team knows they are not expected to read emails in the evening nor respond. Take it a step further an actively discourage it. I sent a lot of emails at 7-8pm when I was a manager, because that was really the only quiet catch up time that I had. If someone did reply to an email, I’d follow up with them the next day to check on their work hours – sometime they just happened to have flexed their time that day, most of them were bored by shelter in place pandemic rules.

    1. Ann O'Nemity*

      I really like this approach. It works well when the manager (1) shares their own email preferences, and (2) sets reasonable expectations.

      My current manager likes to leave early to pick up her kids from school, and then work on emails after they go to sleep. She’s also been super clear that she has no expectation that we respond to emails until the next work day. This makes perfect sense to me, and I appreciate that she’s modeling flexibility and work-life balance.

  13. irene adler*

    RE: emails

    I’m receiving emails from some outside vendors with a lovely statement at the bottom:

    I am sending this message now because it works for me. I do not expect that you will read, respond to or act on it outside of your regular working hours. Thank you.

    1. I have RBF*

      I love this.

      Sometimes I work odd hours, or I have to deal with with people on the east coast and I’m a late riser on the west coast. I will regularly get 6 am (my time) emails from a person in Chicago. I’m not expected to answer them until my regularly scheduled working hours, so I don’t think anything of it. Sometimes we have to schedule evening and weekend work, and send emails when it’s completed. We don’t expect responses outside of a person’s business hours.

  14. Falling Diphthong*

    Re 1, I want to note that people can have extremely strict boundaries about when they check emails, and expect others to observe similarly strict boundaries, while simultaneously not caring what the time stamp is on those incoming emails.

    For a lot of people, sending an email at 10 pm means “when I finally got a chance to finish off work, after stopping from 3-9 to focus on outside work things” or “when I suddenly realized the answer to that question that came up yesterday, and wanted to type it out before I forgot” or “it’s actually 10 am where I am.”

    1. mlem*

      Yeah, my late timestamps are sometimes because I just kept working late, but they’re far more often because I took a bunch of time off in the middle of the day for some reason, or because I realized something that I wanted to capture while it was fresh rather than risking forgetting it the next day.

    2. Sola Lingua Bona Lingua Mortua Est*

      Email’s intent is asynchronous communication, so the recipient really isn’t supposed to care when it was sent. I guess a lot of people misuse it, though.

      It’d be different if the phone were ringing at 1 am; that’s synchronous communication.

      1. Spencer Hastings*

        Exactly. I think some of the weirdness is caused by some vestigial “early to bed, early to rise” BS. That is: She’s sending emails late at night? Like some kind of irresponsible college kid who stays up playing video games or partying and then rolls out of bed just in time for their first class at 11am the next morning? How unprofessional!

  15. learnedthehardway*

    WRT how to cancel an interview with a rude applicant. Just do it.

    If you are up for a confrontation, feel free to let them know that their behaviour during the process is why you’re cancelling their interview. But if you’re not up for that, tell them that the hiring manager has had other candidates who were a better match and has decided not to proceed as they didn’t want to waste the candidate’s time. You don’t need to discuss the reasons with them. If they argue, just tell them that the decision is final.

    1. Shiny*

      I’m having a really hard time even understanding what Sally hoped to accomplish by announcing herself as a candidate! Why on earth would that mean anything to staff or other clients? What was she hoping to achieve?

      I’d be tempted to let her know exactly why she wasn’t moving forward, but I can understand not wanting to open yourself up to a response, plus, why should someone who hasn’t learned the basics of how to live in a society get that education on the LW’s time?

  16. Ladycrim*

    When I first started my previous position, one of my tasks was fixing our very outdated website. My boss had a habit of going through the site and sending me a separate e-mail for every individual issue he spotted, no matter what time it was. I’ll never forget how hard my eyes rolled when I saw the one that was timestamped at 12:03am Christmas morning. (Technically neither of us actually celebrated the holiday, but the office was still closed and we were all on vacation. He just couldn’t help himself, I guess.)

    1. TechWorker*

      Yay! Thanks for the link :)

      I feel like 28 reports would be a lot (!) for anyone, I wonder whether the LW will eventually choose to go back into management at a company with saner demands :)

  17. Slow Gin Lizz*

    Re letter 4: is it just me or is 28 an extremely large number of people to be managing? That would stress me out enormously. I hope that LW is doing a lot better now that they’re no longer managing 28 people, but also realizes that 28 is way too many and that they may indeed be good at managing if they are only managing a few people.

    1. Green great dragon*

      It’s a lot to be direct managing, unless it’s a really structured job where you don’t have to engage much with the day to day work (I can see it for factory/retail work or call-centre, say).

      If LW’s managing 5 people who each manage 5-6 people that’d be different, though I suspect LW would have said if so.

  18. Chairman of the Bored*

    I assume that all the professionals I work with are capable of managing their own schedule in whatever way works best for them.

    As long as I get the information I need when I need it I don’t read anything into email time stamps. Why do I care if somebody wants to work at 10PM or 2AM or whenever?

    1. Peanut Hamper*

      This! It’s not on me to manage other people’s working lives.

      What’s on me to manage is when I receive my emails. I don’t have work email on phone (never have and never will; if work wants me to respond to that 24/7, they need to provide the phone and change my pay from $$ to $$$$). Everybody knows when I work; I shut my laptop down at the end of my workday and will just deal with anything that comes in afterward first thing tomorrow.

      Even when I was teaching, I had a cut-off and told students and parents that I don’t look at email after 4:00 pm, which is when I left the school building.

    2. neeko*

      I care much more about it “setting unreasonable/unfair/unexpected standards” and less about it looking bad. It was definitely an issue when I was in a union.

    3. Maureen*

      As a manager, I’d care greatly about that. I can’t stop what I don’t see, granted, but if I do routinely see out-of-working- hours emails, it is my responsibility as manager to find out what people aren’t completing during work time that they have to resort to work at 10 pm, 2 am, etc. Exceptions happen, of course, like personal emergencies; my vacation starts tomorrow and I forgot to send this file; etc. But as a matter of course? Again: what’s going on? Are people taking on too much? Over-promising deliverables to others? Need guidance on time management? That’s part of managing.

  19. Bookworm*

    Yes, it does. It puts pressure on people, even if this is just you who forgot to send during business hours. Had a boss recently who would send emails at like 11 PM or 3 AM. Staff were not expected to respond to those emails but in retrospect it was also a sign they had terrible work boundaries for themselves and the employees.

    If you can, please try to use a schedule ahead feature. Even if it’s super early in the morning. Or put something in the headline like “not urgent, I just forgot X” in the subject line. That can go a long way.

  20. Bookmark*

    I always wonder about a similar issue to the late night email question, which is late night document review. I am at my most productive editing and writing mode after about 9:30 pm, so it’s often when I make time to do those tasks. However, all my comments/tracked changes are then tagged with the time I did them…

    Sometimes I go to the trouble of deleting the metadata on the comments, but that often is more obtrusive than just leaving the date in the way it is.

    1. Still*

      Deleting the metadata sounds like a huge overkill to me. Do you really check timestamps on other people’s comments? And feel any particular way about them?

      I feel like it’s slightly different with emails because they are directed to a specific person and require a response (even though of course they’re means of asynchronous communication). But timestamps on other work you do… I don’t know, maybe it’s because my workplace is really relaxed and flexible, but it would never occur to me to even consider it.

  21. DataSci*

    I think a lot depends on whether people have work email on their personal phones, so that they’re getting alerts whenever an email comes in. I don’t, so if I choose to not check work email after hours (which is what I do), I can easily enforce that – so when the emails come in at 9 pm from my colleagues in California, or at 4 am from my colleagues in London, I neither know nor care. But if someone’s texting friends after hours and sees an alert about an email from The Boss, that’s a different situation.

  22. Brooke Lynn*

    I’m a big fan of scheduling emails vs. sending at oddball hours. My main reasoning is because I’m often seeking information/need a reply and I want the recipient to be in the right frame of mind to respond thoughtfully and in a timely manner. Friday afternoons have become my time to wrap up loose ends before the weekend so I often schedule the information/proposal request emails to be delivered on Monday around 10am. Mainly because I don’t expect (or want!) anyone to reply on Friday afternoon, but I also don’t want to forget my request.
    I know I could turn off emails for evenings/weekends, but I don’t because of the major “what-ifs”. Realistically, the after-hours emails create a sense of dread and anxiety as they are just adding to my to-do list for the next day. Also, if a colleague is sending them, I’m thinking, should I be working? Why is she working now? Why does she have so much more work than I do? Why are her hours so random? It goes on and on….

  23. Not a Real Giraffe*

    I remember reading Letter 4 before but its reappearance is so timely for me. Today, I am debating an offer for a role that is definitely lower-seniority and a significant pay cut, but I think would improve my quality of life overall. I think part of my hesitance is definitely “the devil I know versus the devil I don’t,” but there is also a part of me that is embarrassed by wanting the lower seniority and further embarrassed by getting paid less than I am currently making (not that anyone but me or my partner would know that). This was a helpful perspective!

    1. Somehow_I_Manage*

      That was definitely the most relatable of the letters. It’s hard to walk away from conventional “success” when it’s available to you- even if the stress isn’t worth the recognition. Plus, we’re all by nature somewhat competitive- it’s hard to not feel strange about leaving a desirable opportunity that you earned.

      At a minimum, I think it’s healthy to convince yourself that even if you leave and it turns out to be the wrong decision, it doesn’t preclude you from another course correction. Our needs are constantly changing. Adaptation is our way of life!

    2. Josephine Beth*

      A few months ago, I moved from a management role supervising a team of 20 to more individual contributor role on a small team. I still have leadership opportunities, as we work with a lot of other similar teams in other states, but I don’t have direct reports. I was really worried about the implications of not being seen as a manager, even though I knew I needed some kind of change.
      It has absolutely been a positive for me, and my family tells me all the time how nice it is that I’m present for things again. I have time to workout, time to visit friends, and time to actually read books! At this point in my life, and with my particular family circumstances, having that balance in work I can be passionate about while also having time to relax is really important to me.

  24. Orora*

    I work in higher ed. Academics tend to work all sorts of weird hours. Just because someone sends me an email at 3am doesn’t mean I need to respond at 3am. I rarely check my email outside of work hours because we’re not doing brain surgery or fighting fires. We just don’t have that many “emergencies” that require email outside working hours. If something truly dire happened, my boss would call or text me. We both have boundaries and understand what an “emergency” really is. (And no, Dr. Faculty, it is not “We’re out of coffee”)

  25. Chairman of the Bored*

    I think virtually all email apps and devices have a means to hide notifications during the recipient’s non-working hours.

    If getting emails at odd times is a problem for somebody, it seems to me that they’d be better off to set their email up such that they don’t get that notification outside of business hours rather than waiting for everybody else to either work on their schedule or use scheduled email delivery in order to make it appear as though they do.

    Just make your phone not tell you about my midnight email until 8AM, and then it doesn’t matter what I do.

    1. So they all cheap ass rolled over and one fell out*

      My team is discussing this issue, not just emails but chat messages. Some people feel really strongly that you shouldn’t send chat messages outside of normal business hours. I feel less strongly, I must admit, but in my opinion, those people should turn off notifications, or sign out of the app on weekends, or just uninstall the chat app (there’s no requirement that people install the email or chat apps on their phone). More than once, I have asked or answered a question in chat on a weekend, and if two employees choose of their own free will to work outside of business hours, what right does a third employee (who is not a supervisor or anything) to block that communication?

    2. TechWorker*

      I might be biased because I work with people in timezones both ahead and behind, so always come in in the morning to a steady stream of email. I spend approximately none of my brainpower worrying about what time it was for them when they sent it…

      I do think it’s important for managers to set good expectations for their reports, but tbh I have some reports who work funny hours because it works for them (Eg 10.30-4 and then a couple of hours after their kids are in bed) and I don’t expect them to pretend they’re not working in the evening.

  26. Underrated Pear*

    For #2, the suggested email wording is a rare case where I don’t quite agree with Alison’s script. If I were a candidate reading that email, I would be really confused. The first sentence sounds like they need to re-schedule the interview; the second sentence sounds like they are calling it off. I would be freaking out over how to respond – do I say “okay, thanks for your time, goodbye” and risk being wrong? Or do I clarify if they want to reschedule and risk looking clueless?

    I know it’s an old letter, but for anyone needing this advice in the present day, please don’t word it as “Change of plans, we need to cancel on Wednesday” and be clear “Change of plans, we will not be moving forward in the hiring process.”

  27. Sharks Are Cool*

    It does bother me when my coworkers send emails at odd hours. I’m staff working closely with faculty in higher ed, so when I receive emails from them timestamped at 10pm on a Sunday I guess I judge them for having poor work/life balance–and it makes me feel like I have to draw stronger lines to defend my own boundaries. It probably wouldn’t bother me so much if it didn’t highlight other disparities: they are working career jobs they are passionate about and are well-compensated for, whereas I am here mostly for the health insurance. So, I’m not saying I necessarily SHOULD feel weird and annoyed about it, but Alison is correct that people below you in the organization will notice.

    1. Onward*

      I’m with you. I guess I’m not bothered as much by like my Grandboss sending out late emails, but I once had a person on the same level as me make SUPER CLEAR that she was regularly working after she put her kid to bed (this was after a full day of work). I have a kid too, and by the time I got my 8-10 hours of work in, got the kid home from daycare, did all the ‘home stuff’, and put him to bed, I would start getting IMs and emails from her.

      It may have been unreasonable for me to feel this way, but I was irked by that behavior. It felt like she was trying to show off how dedicated she was and contributing to a culture where we were ALL expected to be logging into work after a full-day and putting the kids to bed. I just wanted to sit on the couch and veg after a long day and I felt guilty about it.

  28. Sad Desk Salad*

    I have a friend who just informed me she was laid off for reasons that ostensibly were not her fault, but she’s had months of struggling with her boss, who criticizes her judgment. (We’re both in-house lawyers, so judgment is pretty important, and if your style is different from your boss’s it can cause issues.) One example recently was when she completed a task around 9 pm, and decided it could wait till 8 am to send it out. She was roundly criticized for not sending it late at night.

    In my scenario, employees, clients, and vendors are scattered across the globe, so I wake up at 6 am with a mailbox stuffed full of messages from Asia and Europe. I spend my morning shuffling through them all, then get to the heavy work in the afternoon when the emails start tapering off. It’s not uncommon for me to get to something later at night, only for it to hit a Spanish colleague’s inbox right as they’re starting their day.

    So I guess it really depends on the company and the culture. If you’re a global company that knows no operating hours, go ahead and send it. But if people turn off their computers at 5 pm, go home and don’t think about work until 8 am, yeah, maybe wait.

    1. Where’s the Orchestra?*

      I think this is the key with late night emails – what is the rest of the company doing? And how big is the company – multinational company spread all over the globe – who cares what time is on the email. Small mom and pop local place – wait till normal hours – and judge the place individually based on what you know.

  29. BL73*

    It absolutely does not look bad to me if you send a late email. I trust my team to work the hours that work best for them and their families and if they take off during the day and work at night, that’s fine. I don’t judge them – in fact, I find the posters saying they judge people for having a poor work life balance based on late emails incredibly short sighted. It used to be you were forced to work 9-5 only and now we allow people to flex their schedules to actually attend a school event or go to an appointment.

    We are adults, we work when it’s best for us while still meeting the needs of the customers and we definitely don’t judge each other if someone is online at 10 p.m. catching up. What an odd thing to judge someone for.

    1. Green great dragon*

      I did wonder if this was a pre-pandemic letter. We’ve got so much better (on average) at realising that options beyond 9-5 in an office can work for people and for companies.

  30. Onward*

    LW #2 — I would totally let a job candidate who was rude to my staff know that their behavior was the reason the interview was being cancelled. I feel like people who act this way think there are no consequences for their actions because everyone always beats around the bush with them instead of being direct. I can see reasons for deciding NOT to go this route, but I just like the idea of a person like that knowing that it was their behavior that lost them the opportunity.

  31. Ordinary person*

    For anyone who is also dealing with the same issue as the last letter writer –

    It is okay not to like being a manager.
    It is okay to prefer to do the technical work, rather than management. Lots of people say, “Engineering is fun. Management is boring.” (There are even people who say, “Spreadsheets are WAY more fun than going to management meetings.”)
    There is more than one definition of success. If work is consistently making you miserable, it’s probably not a success.

    I was glad to see the update from the original letter writer and I hope she continues to be happy in the new role!

  32. AthenaC*

    It’s interesting reading the responses here, particularly those that recommend scheduling emails even while acknowledging that there can be technical issues with doing that. Against that backdrop, almost seems like scheduling emails can be more trouble than it’s worth? Or maybe not – probably depends on your environment.

    At my company it’s just generally known that at any given point during the year some team / department will be busier than usual and will be sending emails at nonstandard hours. Also some other people (when not particularly busy) will flex their hours sometimes. Pretty much everyone above a (minimal) level of seniority has a great deal of control over their working hours. So – emails are flying around 24 hours a day, and people get to them when they get to them. Recipients are expected to be adults and not read too much into when an email was sent.

    If someone REALLY needs me and ONLY ME when I’m not working (rare but it happens maybe twice a decade), I have a cell phone that can receive phone calls and text messages. I’m fortunate that no one has abused this, but in a functional company it’s good to have this “in case of emergency” option.

  33. Cyndi*

    I want to say, in principle, it’s fine to send emails at the time that works for you! But I think in practice it can depend a lot on context–office culture, context, the relationship between the people involved.

    The tiniest company I ever worked for was four people–the owner, her full time assistant of several years, and two of us part time doing packing/shipping. While the owner was on vacation, a crisis came up–a bulk order way bigger than we were used to–and the three of us jerry-rigged a solution. Owner came home early, wrote off our solution, and waffled endlessly about deciding how to handle it instead. So when I got an email from her at 2AM on a Thursday saying “[ASSISTANT] has been fired, you’re the new full time person now,” I knew I was living on borrowed time, because it was the last in a parade of red flags. Whereas if the office was reasonably functional, and she’d sent an email at 2AM on a Thursday going “Hey, I just had an idea, let’s discuss it when you come in tomorrow,” I wouldn’t have raised an eyebrow.

  34. Bad Wolf*

    I just include a line in my sig file that says that my work hours may be different from the recipient’s and to please not feel obligated to respond outside of the recipient’s regular work hours.

    Email scheduling only works if my laptop has outlook open and is connected to our VPN at the scheduled time. If I am traveling for work, I might be on email at 10 PM to respond to something and then have to punt to the airport at 6 am the following day for an 8 am flight. I’m not going to have a laptop open and on the VPN until I’m home at noon, and then I’ve delayed providing information/asking for feedback/what have you by at least a half day. Add in my colleagues and clients on the opposite coast?

    What I am very careful to do is encourage people to set boundaries, not be in their email all the time, be clear that I am not nose-in-email-on-phone when I am PTO and encourage others to do the same. I also do make a habit of telling people when they start on my teams that occasionally my schedule will require that I send email at odd hours. That is a function of MY schedule, not theirs. If I need something *urgent* I will text or call. And I do not EVER text people out of hours unless the information need is absolutely critical.

  35. Czhorat*

    To be perfectly honest, I only look at the time stamp on an email insofar as it lets me know how long someone has been waiting for a response. I broadly agree with Allison that you don’t want to set an expectation – for yourself or others – but I also feel that we can overthink things like this.

    I think we should normalize the idea of sending the email when it’s convenient for you to send it, so long as it doesn’t impact anyone else’s schedule.

    1. Dinwar*

      This is my view as well. I get migraine-induced insomnia sometimes, and getting some work off my plate is as good a way to pass the time as anything else, so occasionally I’ll send emails at late hours. I’ve started adding a note like “This can wait until morning” or “Let me know by COB on Friday” or something, to let folks know that I don’t expect an immediate response; all I really want is to take this off MY plate and put it into THEIR plate, for them to deal with at their convenience.

      And culture matters. How people use different communications technologies matters. For some people email is for “This needs done, soon-ish, but don’t stop what you’re doing to take care of it” method. And if that’s the case, send them the email whenever; they won’t care anyway. In other work places, an email means “Drop everything and jump on this”, in which case schedule the email for the morning. The point is, without knowing a lot more about the culture of the workplace, the coworkers getting the emails, and the individual proclivities of the folks involved, no useful answer is possible.

  36. Heffalump*

    No job is worth being on blood pressure meds, much less two of them, at any age, much less age 31.

  37. Caramel & Cheddar*

    I am someone who schedules emails because I don’t want people with their own poor boundaries to feel like they have to reply if I send something at a weird hour for me, but I’m also absolutely never going to check emails outside of my work hours so I don’t care if people send them to me at all hours.

    For me it boils down to the fact that I can control my own behaviour but I can’t control other people’s. I can make the choice to use a send later feature and to turn off my email at the end of the day; I can’t make that choice for other people.

  38. IndyStacey*

    I do use delay send, but I also just added the following statement to my signature:

    “I sent this email at a time that works for me. Please do not feel obligated to respond outside your working hours.”

    It has been very well-received.

  39. generalorgana36*

    I actually get great joy out of using the scheduled send feature on Outlook. Not just for late night emails (if I see something easy enough to respond to as I’m watching TV, i’ll just knock it out), but for things throughout the day.

    For example, I put together agendas for a number of calls throughout the week. I let my colleagues labor under the impression that it takes me a bit longer to put these agendas together than I actually take, as I use the delay send function on emails to send the agendas about 45 minutes before each call, even if I’ve been done hours earlier. It frees up my time to actually accomplish other work without remembering to send this email hanging over my head, or to take a walk, or generally mess around (within reason, of course). Often, they bother me a lot less when they think I’m still working on the agenda before the email actually goes out.

  40. CatMintCat*

    My insomniac nightowl boss often sends emails at 2 or 3 am. He is very clear that he doesn’t expect replies then, as he knows we can sleep, but it’s when he clears his to-be-done list as much as he can.

    In our environment, it’s not an issue.

  41. Introvert Teacher*

    “Schedule send.” I will set it to send at the first minute my workday starts the next day.

  42. Just Another Fed*

    If I can deal with my early bird coworkers sending me 7:00 a.m. emails, they can deal with me and my late shift self sending them 7:00 p.m. emails. Using delayed send to send them after I arrive in the morning just means they don’t even get to see the email until halfway through their work day. I’m not expecting them to answer in the middle of the night (and I trust they do the same courtesy of not expecting me to answer hours before my scheduled start time!) If I get an email sent at 10 p.m. or 1:00 a.m., my first assumption is that the sender is in a different time zone, not that they’re expecting me to work through the night.

  43. CSRoadWarrior*

    I don’t see it as an issue, but I wouldn’t count on getting many replies either. Most wouldn’t want to answer emails at odd hours, or on a Saturday. So I would say go ahead and sent it. Just don’t expect a reply immediately.

    However, I wouldn’t advise sending an email at odd hours saying something urgent needs to be done. If urgent, please send it during normal business hours.

  44. RB*

    I do this all the time. So frequently, in fact, that I’ve put a line in my e-mail signature that says: “I am working flexible hours and may email outside business hours. I do not expect a reply at these times.”
    I got that tip from someone on here, so thanks to whoever that was. I like this wording.

  45. Catabouda*

    I’m amazed at how many people worry about email send times. It’s a different world y’all. People work when they can, not just during “business hours.”

    1. Maureen*

      But that doesn’t apply to all business hours. Also, flexible hours are typically arranged ahead of time.

      As a manager, even one of my 5-team member is sending emails routinely outside of regular working hours, I need to know why that is, not only to help ensure a good work-life balance, but also in fairness to other people who rely on getting what they need from their co-worker -in my case, during regular business hours.

      What’s odd to me is the thinking that it’s okay to work when ya want to! It’s not practical in a lot of scenarios.

      1. Catabouda*

        That’s the whole point of flex time. It’s not your job to ensure someone’s work life balance. They are adults making decisions that are best for them. If they are getting their deadlines met and deliverables to their coworkers on time why do you care if they are working from 1 – 5 am but not working in the afternoons?

    2. Anthony-mouse*

      The problem becomes when people are expected to work. I’ve been specifically told by my job that for any external emails, they are only to be sent out 8am to 4pm because otherwise customers will start sending us urgent things for 7:30am at 6am that morning rather than before 4pm the previous day

  46. Good Enough For Government Work*

    I’m an extreme night owl, and some tasks really ARE easier for me to complete at like… 10pm, when my brain is functioning on all cylinders and there are minimal distractions. Also, when my ADHD is playing up, returning to the computer after a brake for dinner and giving myself a strict time period to complete #Task is the best way to get the damn thing done and not keep my colleagues waiting.

    I will often schedule emails, but sometimes it’s not possible or I just forget. So I (and a number of my colleagues) have a short line at the top of our email signatures that reads something like “Due to flexible working, I will sometimes send and reply to emails outside of normal working hours. I do not expect you to read or reply to emails outside of *your* working hours.”

    So far, it’s worked well for us! (And in my case, the COVID-enforced move to wfh has been an absolute godsend, really.)

  47. Persephone Mongoose is back*

    WRT scheduling emails: it really depends on the company culture. I currently work for a global big tech company. We operate around the world and around the clock. I’m in operations so I have direct reports working during my night. It’s very common to get instant messages and emails at all hours. Nobody looks at the time/date stamp. Nobody cares. We are all encouraged to disconnect. It does make it easier to get pulled back in but a lot of us have migrated to having two mobile phones: one for personal use and one for business to make it easier to be off the clock. Only the on call person for that week is required to respond to major issues. That person loops the rest of us in if it’s an all hands on deck situation. At another company I worked for, it was a bit funny that my boss, the company controller, and I all had terrible insomnia and were frequently up at 2 or 3 am working. We joked about it and just worked with it. Lots of stuff got done in the wee hours of morning by the three of us because our work was intwined. But there was zero expectation that we’d be there. We all knew that if we could sleep, we slept. If we couldn’t, well….we had something to keep ourselves occupied.

  48. Delta Delta*

    I had a terribly toxic boss who worked odd hours and would send emails at all hours. I’d wake up in the morning and see that I’d have a bunch of emails from him. some were normal things like, “I’m taking the Jones file for tomorrow” or whatever. But then there’d be some peppered in there that were more about how either the business was failing or how he was the only one working at 3 a.m. or some other weirdness. It got to the point that if I saw I had emails in the morning I’d have heart palpitations and start to feel physically ill.

  49. H3llifIknow*

    I just wanted to reassure the person looking to step away from a management role “back” to an individual contributor and is feeling like it’s a failure. IT IS NOT. I did EXACTLY this. Left a job managing ~25 people, spend plans, contracts, finding them work when a contract ended, constantly hustling for new business, traveling, doing evaluations…and so on. It was exhausting. When I finally said, “I can’t do this anymore” and left it was…. UHMAZING. I love my work. I love my team. They seem to love me, and I’m making so much more money than if I had stayed. And I choose my hours. I end my work day and when I end it.. it is over. This is NOT going backwards; this is progress. Progress on YOU and on work/life balance and happiness. I wish you the best!

  50. MCMonkeyBean*

    I added my work contact information to my home screen on my phone, and now when I have a thought late at night I want to address in the morning I just send myself a quick email. I honestly do this a lot for personal notes to myself (like “do laundry” or “clean cat litter”) just because I know my work email is the first thing I’ll check in the morning, but it seems like it would be good for things like this to just message yourself “email Jane to reschedule the meeting for Thursday” and then you can put it out of your mind and deal with it tomorrow.

  51. Asynchronous*

    Seriously? People work different schedules and have different cadences. I can’t imagine anyone looking askance at email sent whenever or thinking they had to answer it immediately. Email is an asynchronous communication mechanism. Thst means you send messages whenever and reply whenever, each party acting when convenient to them. It’s not that hard.

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