Life Hack: Fill in E-mail Recipients At the End

Ever sent an e-mail before it was finished and then had to send a second e-mail to apologize and admit your toddler had been sitting on your lap and hit the send button with their jam-laden finger? No?

Me neither…


A trick I’m employing more and more these days: fine-tuning the content of every e-mail before adding in the recipient(s).

In the past, my first step when composing an e-mail was to fill in the recipients. Because of the nature of my job, this can involve a complicated web of Cc (and even Bcc) contacts. But it made sense, right? I was a start-at-the-top-and-work-my-way-down sort of communicator because that’s how it’s always been done.

Frustratingly, though, I was regularly finding that by the time I got to the end of my message, the content had shifted enough from my original intention such that I needed to add or remove recipients. So then I’d have to circle back to the top and spend time agonizing over making sure I had the right people removed and the right people added in – all while making sure I didn’t accidentally hit “Send” too early.

Can I just say – it is so much easier to tackle this step after the e-mail is ready to go out the proverbial door?


Not speaking from experience here, but I’m sure there are horror stories of people preparing an e-mail rant about a colleague or tendering a resignation only to get an apology or promotion in their inbox; cue relief and a mad scramble to delete the damaging draft only to inadvertently hit send.

Ugh.

While I can’t help you with the content of your e-mails, I can suggest you start adding in the recipients after the content is completed as one way to avoid awkward digital interactions.

*Full credit goes to my husband for this hack – it’s something he’s been doing for a while, and since I’ve adopted the same practice it has almost certainly saved me from numerous awkward or unnecessary follow-ups.

Would this tip have come in handy for you in the past? Any other great e-mail hacks?

Header photo by Solen Feyissa on Unsplash

17 thoughts on “Life Hack: Fill in E-mail Recipients At the End”

  1. ooh I love this idea, thank you so much for sharing. I feel like I most probably have sent emails that I later wished I had reworded or not sent at all but I cannot remember any actual instances. I will most definitely be using this from now on, thank you!

    1. It just eliminates one potential source of regret/headaches and doesn’t make any extra work. If anything, it saves time. It just is hard to wrap my head around doing something in a different order!

  2. Attach the attachment before you do anything else!! When will I learn to actually do this? So many times I click send and then immediately have to send another email with the actual attachment. I wish draft emails were actually set up like this:
    Attachment(s)
    Text of email
    Sender information
    That’s the order we should do things!

    1. SUCH A GOOD POINT. Yes. Yes.
      I fall into this trap more than I should. At certain points of the year, I can potentially send a specific attachment dozens of times a day. And I forget more than I’d like to admit.
      When I’m writing an e-mail from scratch where I mention an attachment, I add it in as soon as I write about it. But sometimes I have pre-drafted e-mails that I don’t have to fully re-read and that is when I am the very annoying person following up with the attachment. Or, worse, having the person respond asking me to try re-sending the attachment.
      Thanks for bringing this up.

    2. This is an excellent comment to an excellent post! I’ve sort of unofficially done the sender address last, but not as a system. I think will be a system for me from now on. I use Gmail and the reverse send is pretty short.

      Also, maybe a substep for changing the recipient’s name when I am essentially sending a template email. Fortunately, I don’t have any stories to the contrary but I always triple check!

  3. I always try to do this if I feel like it’s maybe a sensitive email or something I need to make sure to get “just right”! (i.e. someone I would be embarrassed to goof the email to – or who I wouldn’t want to see my “first draft” until I had everything in as I want it.) I don’t really have any hacks….My only borderline hack would be that since I use Gmail, I also use Google Tasks (which is always open automatically on the side bar). I love being able to drag time sensitive emails over there- and it automatically creates a “to do” item on whichever list I dragged it to. Then when you click on that item in the task list, it automatically opens the email too. I especially love to use this if there’s something I need to respond to/ do from an email I received (like say fill out a google form response about something or sign up for bringing a treat for a school event by a certain date) but I don’t have time in the moment. It stays in my regular inbox, too, but that extra reminder copied over on the task list is PRICELESS for me! I can add little notes beneath it, set an alarm/ deadline, etc too which I love. Anyway! That’s my only “email hack”. šŸ™‚

    1. I had no idea you could drag items over like that to the to-do.
      I used Google tasks for a while and loved it, but it has fallen off my radar. Time to resurrect it!
      This is a great hack and such a big one because it applies to both work and personal tasks equally. Very handy.

  4. Oh yes, I do this. I have hit “send” unintentionally and prematurely too many times.

    Another good hack: one of my pet peeves is when people don’t respond to all inquiries/questions in my email, so what I do when I respond to someone’s email is to copy their email into my reply and then systematically address all the questions (and delete parts of the original email in the process) until I get to the bottom. This way I make sure to not miss anything important.

    1. We are kindred spirits, San. I cannot count the number of times I have ranted about people not responding to all my questions. I lay things out SO clearly (numbers, bulleting, bold; I have a very specific system), and they’ll respond and just tackle the first few. And these are people that have worked with me over time…so no excuse for not knowing.
      Did they not read the whole e-mail? Do they not have answers for the questions they skipped? Who is responsible for following up.
      At one point, years ago, I told a specific person I was managing that they HAD to respond to every single question I sent.
      In my current working environment, I’m very blessed to have people that respond thoroughly and almost always respond below the questions a different colour text. This is so helpful! Sometimes the response is even highlighted.
      Another thing I appreciate is when people embed screen captures into the body of the e-mail instead of sending them attachments. When it’s just a picture or something static (i.e. not a shared document or excel worksheet), I really appreciate having the visual at the ready in the body of the e-mail when it makes sense in context…

  5. That is a good hack to use! I will have to try it out! I like NGS’s suggestion of adding the attachment first, although my work email is smart enough to provide a pop up if the wording of the email indicates there is an attachment and nothing is attached.

    I am blocked from using gmail and most google applications at work which really really sucks! That means that 99% of my emails are typed on my phone! Since I work in financial services, things are so locked down at work which I understand but also annoys me because I try not to use my work email for personal email!

    1. My work-email does the pop-up thing too, but I often work on an e-mail client on my laptop and that way it DOESN’T make the recommendation to add an attachment if it appears to be missing.

      What a nuisance about your work/personal e-mails!

  6. Emphatic YES to this life hack. I started doing it as well years ago after a mishap that still makes me cringe. In brief: wee 25-year-old me was once in charge of creating the shortlist for hiring a new teacher where I was working at the time, which involved a lot of forwarding candidates’ submissions to my boss, usually with little summaries of what I thought of them…. and then once I hit reply instead of forward, so the candidate received her own summary. It could’ve been far worse, to be honest – my comment was fairly innocuous (something like “looks interesting but not much experience”) but remembering it still has the power to turn my cheeks red to this day, a full ten years later. So big big YES from me to filling out the recipient last!

    1. Eek. That sounds very traumatizing. Even if it could have been worse, those sorts of little gaffs can really put one on edge moving forward!

  7. YES, virtual high five. I have done this for the past 20 years or so. I always add in the recipients later or if it isn’t an address in my contacts yet I copy it into the cc place. Email just can’t be send then even if you hit it accidentally. I do the copy in cc also when I reply to an email.

    I also learned early on in my career to. structure emails by topic and projects. If I have two projects with a person I send two separate emails. this why filing away is much easier and you don’t get mixed up in topics. And I tend to work a lot with bulletins and easy “instructions” no one has time to go through a lot of fluff in emails.

    I should take NGS advice to heart in copying in the attachments beforehand. I can improve here and reduce sending such double emails.

    1. Yes! I definitely prefer when people separate e-mail threads by project/topic. I have a LOT of e-mail folders (and subfolders) and it makes life so much easier when an email falls into one category/project partner/report.

  8. I do this too, particularly with those sensitive emails. I also do it when forwarding or replying only to one or two individuals on a group email – I clear the “to” list and then start from scratch.
    I also need to adopt NGS’s approach to attachments – if I had a nickel for every time I sent two emails to get an attachment to someone…
    And YES on the separate emails for separate topics! Why do people group all sorts of different things in the same email? Drives. Me. Bonkers. šŸ™‚

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