True Advice from People Who Are Truly Bad at Email

There’s a quote attributed to Bill Gates that I recite all the time: “I choose a lazy person to do a hard job; because a lazy person will find an easy way to do it.” I love it because it captures a sentiment I’ve always found to ring true: There’s a way to turn a vice into a virtue. Lazy people are the best at finding easy ways to do things. Messy people have the best cleaning tips. And people who are self-admittedly awful at managing their inboxes have the best advice for communicating via email.

I’ve rounded up some solid advice from wishy-washy emailers right here for you to prove it. And yes, names have been redacted to protect their inboxes.

“Unless you absolutely have to, don’t send an email to more than one person. I’m less likely to reply to it because I’m waiting (and hoping) to see if the other person does.”

“I have begun to tell people in my emails, if you don’t hear from me by [reasonable date], please nag me exactly that morning with an all-caps subject line. Once they know I’m serious, I think the permission to nag helps keep things moving along, even when one of us drops the ball.”

“The use of action instructions in the header saves me all the time. Basically, type your email with the recipient and title, then tell me what you need. Something like ‘ACTION REQUIRED: Next years numbers,’ or ‘FOR REVIEW: Use of account XYZ,’ or ‘RESPONSE NEEDED: tomorrow’s meeting, spreadsheet attached.’ If I see one of those bolded action instructions I usually prioritize it, and if I am the sender, I have a wayyy better response rate.”

“When dealing with people who suck at emails, I send them numbered lists of questions I need them to reply to.”

“Auto response is a lifesaver! I’m a one-woman show and frankly, not everything that comes through my inbox is top priority.” This busy woman has her business account auto-reply to each email, with a message that invites clients with urgent requests to text or call, and sets an expectation for her reply: “If you have not received a response within 48 hours, please follow up.”

“Labels are a must! I can easily sort through everything that way. I set up filters to automatically archive (skip the inbox) on things that don’t need immediate response so it keeps my inbox manageable.”

“If it takes you more than two sentences to deal with the issue in an email, you’re probably better off having a conversation by phone or in person. Put as much detail in the subject line as possible. Emails should look more like texts than cards from your grandmother.”

“Don’t just continue to reply to the same email thread indefinitely if the topic changes. It is usually best to either change the subject line of the email, or better yet, start a new email. When you get 100+ emails a day, you need to be good at prioritizing responses, so if I don’t know what an email is about, or think it’s about an old topic, I’m less likely to open it promptly. And it is especially useful when you need to go back and search old emails if the subject line matches the body of the email.”

It seems counter-intuitive, but many of the people we asked said their smartphone makes them worse at email. “This is a rule I’m trying really hard to implement for myself: Don’t check your email unless you are available to answer emails. I end up forgetting to answer some emails or putting off my response because I read it and then forgot that I never answered. I’m trying really hard to only check if I have time and mental energy to respond right at that moment.”

“I have ’email’ in my daily calendar and I try to stay off of it until that time and once that 30 minutes is over, I close it.”

“I suck at email, but like five years ago, Gmail magically started sending everything directly to Trash. I couldn’t figure out how to reroute it, and after a few half-hearted attempts for a week, I found I liked it. Now, I move things out of my trash into my inbox if I want to save it; everything else gets magically deleted every month or something.”

“I suck at email too. After about 8 or 9 years people will just quit emailing you. Hot tip.”