July 11, 2014 7:06 AM   Subscribe

I regularly flake on email responses-- both personal and professional. (I have all the comorbidities you'd expect: ADHD, perfectionism, perpetual writer's block, mild social anxiety, introversion, disorganization, procrastination/avoidant tendencies.) I'm starting a new job and need this particular behavior to stop forthwith. Short of completely overhauling my whole effed-up executive function, is there an ironclad system I can implement to ensure that every single one of those emails gets answered punctually?

Basically, in the event that I (a) know exactly what to say, and (b) know exactly how to say it, I can respond to an email immediately. Otherwise, I pretty consistently end up writing a few sentences, getting stuck at the undecided part (even if it's low-stakes!), saving to drafts, and moving on to something else. The next day, I'll remember vaguely about the email, but feel anxious and procrastinate... ditto next day... voila, a month later and I still haven't sent it and now need to dig deep into the spurious excuse bag even to continue a relationship with the original sender. Occasionally, I'll enter the crazy shame-spiral thing where I eventually respond, but feel so guilty/anxious about being late that I can't bring myself to open the sender's response to THAT email, so then I'm late responding again, etc., etc.

It doesn't help that I have a very scattered, interruption-heavy life (kids, etc.) and a profession that often lacks clear deadlines, both of which only encourage my inherent flakiness. I'm working on forcing myself to make and follow to-do lists, but keep running adrift on the sheer aversiveness and time-consuming nature of email specifically (owing to the writer's block, perfectionism, social anxiety thing), which makes it soooo tempting just to skip that item and move on to my many more pleasant, equally pressing tasks.

Obviously, the ideal solution would be CBT + GTD + a brand new brain, etc.-- but with limited resources of time/energy/money, I need to put off the full remodel and just find a stopgap for this particular, very critical problem. Email procrastinators of Metafilter, what can I try? Has anything made a punctual communicator out of you?
posted by Sockinian to Work & Money (17 answers total) 95 users marked this as a favorite
I feel your pain with late email shame spirals. Inbox Zero + Beeminder helps me deal with every email, even if it's just a one-minute response to be followed up later.

More specifically, I aim to have inbox zero at the end of every day, which means for each email either a) responding and archiving, b) explicitly ignoring, or c) a short reply and a followup reminder set. Writing a big draft and not sending doesn't remove the email from my inbox, and if isn't empty by the end of the day then Beeminder fines me $5.
posted by katrielalex at 7:21 AM on July 11, 2014 [2 favorites]

What helped me:

(Optional step: Routing all email through one viewer.)

1. Clearing my inbox(es) of anything that doesn't require a response. Archived them, deleted them, sent them to Evernote, whatever. Just got them out of there. There are a number of services that make this a lot less daunting than it sounds, especially if you use Gmail. (SaneBox has a 14 day trial during which you can do this, but there are others.)

2. Once that was done, I've tried to stick to it. When it's done, it's gone. That way, what still needs to be dealt with is always easy to find, and stays in my face. Full disclosure: It takes effort. But it's shaped how I think about email. Now they're tasks in a list, rather than amorphous social anxieties.

If you're mostly looking at email through a phone, I've found Boxer to be really helpful, "Quick Reply" especially. And as long as I only allow myself to "To-Do" or "Unread" once.
posted by gnomeloaf at 7:26 AM on July 11, 2014

I echo that the big key for me is making sure that I clear my inbox and leave emails that have not been dealt with, and only those, unread. It really helps to have things staring at you.
posted by OmieWise at 7:30 AM on July 11, 2014

I turn off "mark read automatically" in Outlook, and only mark things read manually if they are info-only. Otherwise they remain unread, which means I haven't responded to them. My goal is to get them responded to.

I find that setting aside the first 10-15 minutes of every hour, PLUS reframing my email prejudice, gets me most of the way there pretty much every day. The email prejudice is just shaking your fist at the sky anyway - it's the tool that is used, deal with it - and I think most things can wait 45 minutes. (You may also find that 10-15 minutes is way too much time, which might surprise you.)

Also, make an effort to do something about the distractions. Whatever you can do to reduce them will make it easier to do your work.
posted by Lyn Never at 8:00 AM on July 11, 2014

I struggle with this sometimes, and one strategy I have used is keeping a document with sample phrases in it. Usually these are excerpts from previously sent emails, cut and pasted into a file where I can reuse them again if I am feeling blocked on drafting a new email from scratch. Sometimes I can cobble together most of a response with them, and only have to add a few linking phrases and details specific to this conversation's needs.
posted by a fiendish thingy at 8:20 AM on July 11, 2014 [8 favorites]

Going further than "a fiendish thingy," what I do with some professional email is use a program like Textexpander or Keyboard Maestro or any other text-clip macro program to have a ton of whole or partial responses I can choose from, either from a drop-down menu or a keyboard command. Go through your sent mail. I bet you'll see a lot of similar emails from yourself. Even just a few canned responses can help. And you *do* have an automatic signature, right? (I have known people to type them up every time!)

Typical canned responses from me:

"Please remove the address from all of your lists and future mailings."
"Thanks for writing. I'll check it out."
"Sorry, I don't have time for something like that, but thanks for considering me for it. I'm flattered!"
"Thanks for letting me know. I'll take care of it right away."
"The person you want is I'm cc'ing them on this message so they can help."
"I can do that. When do you need it?" (This one is highly effective: it pushes vague requests with no due date back to the other person, which is almost completely off my plate and out of my mind.)
"I'm sorry, I'm not sure I understand. Can you explain?" (Also a deferring mechanism -- never abused but always productive.)

I don't feel bad about canned responses seeming insincere. They're not the whole message, they're just part of it. There's always something personal in there, and I always try to address the email to the person in the body: "Dear Jane," or "Jane:".

Additionally, unsubscribe to as many email lists as you can. Turn off as many automatic notifications as possible. Or at least route them to a separate folder; out of sight, out of mind.
posted by Mo Nickels at 8:50 AM on July 11, 2014 [7 favorites]

I think you need to get really strict with yourself about using "save draft." If you find yourself needing/wanting to save a draft, maybe instead you could a) write a quick followup saying, "Thanks for asking about [thing]! I need to look up [other thing] and talk to [person] before I can give you a firm answer but I should be able to get back to you by [date/time]." Cc yourself, then it's an action item and a reply at the same time.

If you're agonizing over the exact wording, just remember: the main point of the email is to communicate. You're not communicating AT ALL if you can't hit send. If people are confused or you say it wrong, there will almost always be an opportunity to follow up later.
posted by mskyle at 9:12 AM on July 11, 2014 [1 favorite]

Personally I can't handle inbox zero. Professionally, I can't handle any other alternative. And the search function is strong enough in outlook, you don't even have to organize your email. Just make it Not Inbox.

If possible, I try to reply the same day. If not, I have Plan B to short circuit the shame spiral.

Late Friday afternoon, I like to go through and reply to all the emails I've been avoiding. It's nice because few people immediately get back to you, so it doesn't start the email spiral again until Monday morning.

"Sorry for not getting back to you sooner, I'm just catching up on my email.

Pick one:


posted by politikitty at 10:44 AM on July 11, 2014 [1 favorite]

I could have written this. I hate email. I suck at email. I have had literal panic attacks over email. Email is the second-greatest anxiety in my life, second only to talking to companies on the phone. If I ever become rich, which is unlikely given that I suck at email, the first thing I am doing is hiring an assistant to handle my inbox for me. But since most of us can't afford to do that, for me this comes down to two components:


* I'm not afraid of email so much as afraid of what the emails will say. It isn't a medium thing. I used to be the kid in school who would always take home report cards and graded papers without ever reading them because I was too afraid to look. Reading email is scary because I have to be confronted with what is potentially bad or soul-crushing news; writing email is scary because it means I have to agonize over a forthcoming email that might be bad.

Unfortunately I don't have a good solution to this. Even knowing that email isn't Schroedinger's Box, that you can't just ignore a hypothetical horrific email out of existence, doesn't help. Inbox zero is a nice meme, but in practice I find it actually makes matters worse. Inbox (3252) doesn't scare me at all, because there's no sense of urgency, whereas Inbox (1) is enough to make me want to vomit.

* Maybe you have a difficult psychological hangup - that you'll word something wrong or unprofessionally. You probably do - in general people don't give a shit about how their emails come off, or they word and reword and agonize over everything. The solution to this is to realize how many bosses and real-life people in the professional world write the sloppiest fucking email you'll ever see in your life, and still get work.

Practical: Boomerang. It's an email scheduler, basically, that works with Gmail. It's very robust - it even understands that "tomorrow morning" on 2:30 a.m. Monday night means 8 a.m. Tuesday, unlike a lot of schedulers. It's good for freelancers or people who don't work 9-to-5 schedules but need to appear as though they do - the same principle as queueing blog posts. But how it helps me is to rout around the anxiety. Sending out an email via Boomerang doesn't feel as awful, because it's not actually sent and I don't have to pre-emptively agonize over the response during the act of composing it. And when the email is actually sent, it happens on its own and I usually forget.
posted by dekathelon at 11:31 AM on July 11, 2014 [6 favorites]

Change it up a little. Pick up the phone and talk to the person, "hey I just got your email... " and if they aren't there leave a message that you wanted to talk about whatever and you're available during whichever hours. Voila, you've fulfilled your end of the social contact. This is of course highly avoidant of the email anxiety, but it may help.
posted by zennie at 12:50 PM on July 11, 2014 [1 favorite]

Totally relate to this. For me, the only thing that works is scheduling a specific time to just sit there and respond to emails. To start off with, make it short- maybe just 5 minutes, or as much as you can handle. Just open one and start writing. I only check my (nonwork) email a couple times a day and then spend about 15 minutes answering everything whether I want to or not...
posted by three_red_balloons at 5:00 PM on July 11, 2014

Here's a low-tech solution that works amazingly well. Put a rubber band around your wrist. If you don't complete an email response within 5 minutes, you pull back on the rubber band, and then let go. I use this as a "behaviour modification" device for many tasks.
posted by LauraJ at 10:41 PM on July 11, 2014 [1 favorite]

These problems are best dealt with using the "one simple rule" technique. Pick ONE rule to fix this and stick with the rule, following it no matter what.

My suggestion is a rule "have all E-mails answered by the end of the day." Even if you can't get a full answer, partially answer it and say you'll get back to them.

This may result in you answering all E-mails at the end of the day. That's fine.
posted by Ironmouth at 3:22 AM on July 12, 2014

Get comfortable with writing short replies (bonus: sounds better) and if possible use a send-remove-from-inbox-and-view-next client like Gmail can do so it's easy to do the right thing.

Emails that require a thoughtful response should be kept elsewhere; reply first with something like "let me think about this."
posted by michaelh at 5:27 AM on July 12, 2014

Boomerang for Gmail allows you to "boomerang" an email - if you haven't replied to it in X days, it shows up as Unread again in your Inbox. It also allows you several other features, such as send later at time X, but FWIW that feature is pretty handy.
posted by IAmBroom at 3:51 PM on July 13, 2014 [2 favorites]

I wanted to add a thought on when to check and reply to email. This depends on your job and your work-load. If you're constantly busy and replying to emails is just another thing to do, I would suggest turning off all the sounds, icons and other flashy notifications that you just got a new email. These disrupt your flow of work, likely making you less productive over all.

Set up a reminder, or set a little alarm, or just remember to check your email once every so often - once an hour, once in the morning and once in the afternoon, whatever. If you really get distracted by the email just being there, always open, you can close/log out and only check it at these designated times.
posted by filthy light thief at 11:52 AM on July 17, 2014

Echoing many here, just try to touch each email as FEW times as possible. I work in this order: delete trash with pleasure to trash; mark important mails needing careful attention to come back to; send pithy replies to all others.
It doesn't require any add-ons in gmail.
posted by dougiedd at 11:49 PM on July 17, 2014 [1 favorite]

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