29 Habits of Highly Effective Emailers: How to Make Your Emails More Productive and More Pleasant

29 Habits of Highly Effective Emailers: How to Make Your Emails More Productive and More Pleasant

The subject of email etiquette is important for a very simple reason: Because everyone lives in his inbox.

At the same time, very few of us — if any — has had any formal training in how to send an effective email. We’re just expected to know how to do it.

That’s regrettable — and rectifiable.

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Jonathan Rick

April 29, 2018
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Transcript

  1. 1.

    29 Habits of Highly Effective Emailers How to make your

    emails more productive and more pleasant. Jonathan Rick hi@jonathanrick.com (202) 596-1882
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  3. 3.

    1. Email: Can’t Live With It, Can’t Live Without Complaining

    About It 2. Managers Wish Their Staff Knew These 3 Truths About Email 3. Here Are 3 Easy Ways to Make Your Emails Friendlier 4. 5 Techniques the Smartest Emailers Swear By Agenda for Today’s Workshop on Email Etiquette
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    5. 5 Courtesies That Professionals Extend to Others 6. These

    3 Email Tricks Will Save You From Unending Frustration 7. 4 Fun Ways to Make Your Emails Stand Out 8. 3 Everyday Emails That Make You Sound Abrupt or Dismissive 9. 3 Rookie Mistakes We’ve All Made With Email Agenda for Today’s Workshop on Email Etiquette
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    “Email might just be the biggest killer of time and

    productivity in the office today. Anyone with an inbox knows what I’m talking about. A dozen emails to set up a meeting time. Documents attached and edited and re-edited until no one knows which version is current. Urgent messages drowning in forwards and CCs.” —Ryan Holmes
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    “Unlike instant messaging or video conferencing, email lets you take

    a step back and consider your thoughts — an unusual advantage in these harried times. It is a space for thoughtfulness, where it’s possible to stand out, to surprise people, to get attention.” —Sarah Begley
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    “Spam, which once threatened to overrun our inboxes, has been

    made invisible by sophisticated email filtering. I received hundreds of spam emails yesterday, and yet I didn’t see a single one. At the same time, the culture of botty spam has spread to every other corner of the internet. I see spam comments on every website and spam Facebook pages and spam Twitter accounts every day.” —Alexis Madrigal
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    “While the mobile web is a rusting scrapheap of unreadable

    text, broken advertisements, and janky layouts, normal emails look great on phones. They are super lightweight, so they download quickly over any kind of connection, and the tools to forward or otherwise deal with them are built natively into our mobile devices.” —Alexis Madrigal
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    “Anyone, no matter how tech savvy or unsavvy, can use

    email from any device, from wherever they are, all the time.” —Farhad Manjoo
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    3

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    1. Email is not always best. 2. By default, email

    lacks tone. Managers Wish Their Staff Knew These 3 Truths About Email
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    “If you don’t consciously insert tone into an email, a

    kind of universal default tone will not automatically be conveyed. Instead, the message written without regard to tone becomes a blank screen onto which the reader projects his own fears, prejudices, and anxieties.” —David Shipley and Will Schwalbe
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    Hey Stanley, Any chance you can cover for me on

    Friday? There’s a bottle of Scranton’s finest white wine in it for you… Jimbo Ok. Jim’s Question Stanley’s Answer
  20. 24.

    Managers Wish Their Staff Knew These 3 Truths About Email

    1. Email is not always best. 2. By default, email lacks tone.. 3. You can create tone by adding padding. This is the most important thing you need to know about email.
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    “Every email I ever send: ‘Hello! I am extremely excited

    to be corresponding with you! You can tell by the number of exclamation points I use! Here is one sentence with a period so that I don’t come across as manic. Thanks!’” —Kathleen Barber
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    Karen, Please see me. Your projector supervisor, Jim Karen, When

    you get a chance, would you mind swinging by my cubicle? Your projector supervisor, Jim Bad Managers Do This Good Managers Do This
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    “As a manager, you can really work your employees into

    a tizzy who can’t figure out whether your terse email is a sign they’re about to get the boot, or just the result of a disappointing Sweetgreen salad.” —Rachelle Hampton
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    Manners impede efficiency. You should always be aware of how

    others perceive you, especially in a virtual medium where information is so scarce. Some People Do This Smart People Do This
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    It’s unrealistic to expect people to craft a perfectly polite

    email every single time they click “Send.” Because of email’s inherent affectlessness, you often need to be a little extra polite. Some People Do This Smart People Do This
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    “Dance like no one is watching; email like it may

    one day be read aloud in a deposition.” —Olivia Nuzzi
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    “A person’s name is to him or her the sweetest

    and most important sound in any language.” —Dale Carnegie
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    Ask #1 How’s the weekly HR report coming along? Ask

    #3 Hi there Toby, How’s the weekly HR report coming along? Ask #2 Toby, How’s the weekly HR report coming along?
  31. 39.

    Ask #1 Hi Toby, How’s the weekly HR report coming

    along? Ask #3 Hi Toby: How’s the weekly HR report coming along? Ask #2 Hi Toby - How’s the weekly HR report coming along?
  32. 41.

    Here Are 3 Easy Ways to Make Your Emails Friendlier

    1. With a greeting. 2. With a pleasantry.
  33. 42.

    I hope you’ve been staying cool during this relentless humidity.

    I hope you had a wonderful Thanksgiving. I hope you’re enjoying the last few weeks of 2019.
  34. 43.

    “If you send me an email that begins, ‘I hope

    you’re doing well,’ I probably don’t know you.” —David Martosko
  35. 44.

    Here Are 3 Easy Ways to Make Your Emails Friendlier

    1. With a greeting. 2. With a pleasantry. 3. With a sign-off.
  36. 47.

    Adam M. Grant and Francesca Gino, “A Little Thanks Goes

    a Long Way: Explaining Why Gratitude Expressions Motivate Prosocial Behavior,” Journal of Personality and Social Psychology, 2010.
  37. 50.

    Delivering World-Class Paper for Vance Refrigeration Did you fix the

    baler? Interesting Article About the Lackawanna River Introduction (Phyllis and Bob) Baler Interesting Article Introduction Proposal for Vance Refrigeration Smart People Do This Most People Do This
  38. 51.

    NEED YOUR INPUT: HR Survey Baby Shower at 4 PM

    – Response Requested Michael, For Your Review: Lunch Menu Quick question about Poor Richard’s happy hour Baby Shower at 4 PM Lunch Menu Happy Hour HR Survey Action-Oriented Actionless
  39. 53.

    Most People Do This Smart People Do This Proposal RE:

    Proposal Subject: Subject: Proposal Status of DMI Proposal? Subject: Subject:
  40. 54.

    Most People Do This Smart People Do This Conference Room

    RE: Conference Room Subject: Subject: Conference Room Are we getting bonuses? Subject: Subject:
  41. 55.

    5 Techniques the Smartest Emailers Swear By 1. Make your

    subject line specific. 2. When emailing a group, tag and task people.
  42. 57.

    From: H <hrod17@clintonemail.com> Sent: Friday August 20, 2010 3:45 PM

    To: JilotyLC@state.gov; Russorv@state.gov; ValmoroLJ@state.gov Subject: Question
  43. 58.

    From: H <hrod17@clintonemail.com> Sent: Friday August 20, 2010 3:45 PM

    To: JilotyLC@state.gov; Russorv@state.gov; ValmoroLJ@state.gov Subject: Question Can you find out for me what the NPR stations I can hear on Long Island are? I lost the WNYC signal halfway down the island can’t figure out from Google what the next stations are.
  44. 59.

    From: H <hrod17@clintonemail.com> Sent: Saturday, August 21, 2010 6:41 PM

    To: JilotyLC@state.gov; Russorv@state.gov; ValmoroLJ@state.gov Subject: Re: Question Did any of this you get this?
  45. 60.

    “When I send an email to one person, there’s a

    95% chance I’ll get a reply. When I send an email to 10 people, the response rate drops to 5%. When you add people, you drastically decrease exclusivity and make people feel they don’t need to read the email or do what you ask.” —Patrick Lencioni
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    0 2 4 6 8 10 12 0 20 40

    60 80 100 120 Recipients Responses (%) The Freeloader Effect ⚫
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    Greetings Accountants, We gottasend the Sabre letter today. Please make

    sure it’s format- ted correctly, please proofread it, and please include the M&Ms. Greetings Accountants, We need to send the Sabre letter today. ANGELA, Please make sure it’s formatted correctly. OSCAR, Please proofread it. KEVIN, Please include the M&Ms. Most People Do This Smart People Do This
  48. 63.

    5 Techniques the Smartest Emailers Swear By 1. Make your

    subject line specific. 2. When emailing a group, tag and task people. 3. Use BCC sparingly.
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    From: Nate To: Pam CC: Dwight Subject: New Cutbacks Dear

    Office Administrator Beesly, Please direct all complaints about Scranton Business Park to the new building owner, Dwight Schrute. I’m CCing him and will let you two take things from here.
  52. 67.

    NATE, Thanks for connecting me with Dwight. DWIGHT, I understand

    you’re the new building owner. I’m the office administrator for Dunder Mifflin’s Scranton branch. Can we talk about the cutbacks you’ve recently instituted? NATE, Thanks for connecting me with Dwight. (I’m moving you to BCC to spare your inbox reply alls.) DWIGHT, I understand you’re the new building owner. I’m the office administrator for Dunder Mifflin’s Scranton branch. Can we talk about the cutbacks you’ve recently instituted? Most People Do This Smart People Do This From: Pam To: Nate & Dwight Subject: New Cutbacks From: Pam To: Dwight BCC: Nate Subject: New Cutbacks
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  54. 69.

    5 Techniques the Smartest Emailers Swear By 1. Make your

    subject line specific. 2. When emailing a group, tag and task people. 3. Use BCC sparingly. 4. Embrace line breaks.
  55. 70.

    Dear Mr. California, The search committee has three questions for

    you: How will your experience selling refinery equipment translate to our smaller scale here? I’m almost a little concerned that you might be overqualified. Do you think that you are? You are a man of great confidence. Could you speak a little more to that and what the role of confidence would be in a dialogue with a subordinate? Dear Mr. California, The search committee has three questions for you: How will your experience selling refinery equipment translate to our smaller scale here? I’m almost a little concerned that you might be overqualified. Do you think that you are? You are a man of great confidence. Could you speak a little more to that Most People Do This Smart People Do This
  56. 71.

    Dear Mr. California, The search committee has three questions for

    you: How will your experience selling refinery equipment translate to our smaller scale here? I’m almost a little concerned that you might be overqualified. Do you think that you are? You are a man of great confidence. Could you speak a little more to that Dear Mr. California, The search committee has three questions for you: 1. How will your experience selling refinery equipment translate to our smaller scale here? 2. I’m almost a little concerned that you might be overqualified. Do you think that you are? Smart People Do This Smarter People Do This
  57. 72.

    Dear Mr. California, The search committee has three questions for

    you: 1. How will your experience selling refinery equipment translate to our smaller scale here? 2. I’m almost a little concerned that you might be overqualified. Do you think that you are? 3. You are a man of great confidence. Could you speak a little more to that and what the Dear Mr. California, The search committee has three questions for you: 1. How will your experience selling refinery equipment translate to our smaller scale here? 2. I’m almost a little concerned that you might be overqualified. Do you think that you are? 3. You are a man of great Gmail Does This You Know Better, Right?
  58. 73.

    1. Make your subject line specific. 2. When emailing a

    group, tag and task people. 3. Use BCC sparingly. 4. Embrace line breaks. 5. Write emails when you’re angry. 5 Techniques the Smartest Emailers Swear By
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    1 Save it in your drafts folder. Send it to

    yourself. Write a few versions. 2 3
  62. 78.

    Let’s Recap How many emails should you send about a

    single issue before trying a different form of communication? 1/5
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    ❌ Checking-in. ❌ Touching base. ❌ Circling back. ❌ Not

    sure if you got my last email? ❌ Hello? ❌ Please reply. ❌? I suspect you’re still reviewing proposals. Please don’t hesitate to let me know if there’s any additional info I can provide. I’m so excited about this project, I thought I’d see if you had an ETA for the kickoff? Sorry to nag you; just want to stay on your radar. When the time is right, I’m ready to re- engage. Most People Do This Smart People Do This
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    5 Courtesies That Professionals Extend to Others 1. They follow

    up without being a pest. 2. They keep others abreast of their actions.
  71. 98.

    From: Jan To: Michael Subject: Where’s That QA Report? Michael,

    Where do things stand with December’s quality-assurance report? Thank you.
  72. 99.

    Michael thinks to himself, “I’m waiting on Creed for this

    report. Let me check with him before replying.” So Michael emails Creed. But what if Creed doesn’t get back to him promptly —or, let’s be honest, at all? That means Michael never gets back to Jan. Dearest Darling Jan Levinson-Gould, Creed’s been managing this report. I just asked him for an update, and will let you know as soon as I hear back. Lovingly yours, Michael Most People Do This Smart People Do This
  73. 100.

    5 Courtesies That Professionals Extend to Others 1. They follow

    up without being a pest. 2. They keep others abreast of their actions. 3. They acknowledge CCing people.
  74. 101.

    From: Pam To: Jim Subject: Our Next Prank Halpert, I

    have a once-in-a-lifetime idea! Stop by when you stop daydreaming. Beesly
  75. 102.

    Absolutely! And let’s include Darryl. Absolutely! And let’s include Darryl

    (who I’m copying); he’s as bored as we are. ;) Most People Do This Smart People Do This From: Jim To: Pam CC: Darryl Subject: RE: Our Next Prank From: Jim To: Pam CC: Darryl Subject: RE: Our Next Prank
  76. 103.

    From: Bruce To: Meredith Subject: Outback on Friday? Meredith Baby,

    I have some more, um, supplies for you. Let’s meet at Outback on Friday. Say 7? Bruce
  77. 104.

    Bruce, As much as I love me a good steak,

    HR says that we can’t continue our arrangement. + Holly Bruce, As much as I love me a good steak, Human Resources (HR) says that we can’t continue our arrangement. I’m CCing Holly, our HR rep in Scranton, so you know this is serious. Most People Do This Smart People Do This From: Meredith To: Bruce CC: Holly Subject: RE: Outback on Friday? From: Meredith To: Bruce CC: Holly Subject: RE: Outback on Friday?
  78. 105.

    5 Courtesies That Professionals Extend to Others 1. They follow

    up without being a pest. 2. They keep others abreast of their actions. 3. They acknowledge CCing people. 4. They include calendar invites.
  79. 106.

    When you have a few minutes, might we chat about

    my commute? As things stand, I’m in Pennsylv- aniaMondays, Wednesdays, and Fridays, and in Florida Tuesdays and Thursdays. Let’s chat tomorrow at 6 AM. Gabe’s Question Jo’s Answer
  80. 107.

    I’ll call you then. I’ll call you then. In the

    meantime, I’m sending over a calendar invite. Most People Do This Smart People Do This
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    5 Courtesies That Professionals Extend to Others 1. They follow

    up without being a pest. 2. They keep others abreast of their actions. 3. They acknowledge CCing people. 4. They include calendar invites. 5. They use hyperlinks seamlessly.
  83. 110.

    Packer, Have you seen this? https://www.rollingstone.com/ tv/tv-features/that-one-night-the- oral-history-of-the-greatest-office- episode-ever-629472/ MGS

    Packer, Have you seen this article from Rolling Stone? That One Night: The Oral History of the Greatest Office Episode Ever MGS Lazy Seamless
  84. 111.

    YoOscar, In China, there are 56 cities with more than

    a million people. https://www.nytimes.com/2012/ 01/18/world/asia/majority-of- chinese-now-live-in-cities.html How do like them apples? MGS YoOscar, According to the New York Times, in China, there are 56 cities with more than a million people. How do you like them apples? MGS Lazy Seamless
  85. 113.
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    Hi Ryan, Please find attached Dunder Mifflin’s new pitch deck.

    It’s 50 MB, so if your email provider blocks it, let me know and I’ll send it via Dropbox. Hi Ryan, Here’s DunderMifflin’s new pitch deck. I’m sending it via Dropbox because its size (50 MB) might prevent delivery to your inbox. Most People Do This Smart People Do This
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    These 3 Email Tricks Will Save You From Unending Frustration

    1. Avoid sending big attachments. 2. Delay the delivery of your emails. This is the first thing I do when I create a new email address.
  89. 118.

    These 3 Email Tricks Will Save You From Unending Frustration

    1. Avoid sending big attachments. 2. Delay the delivery of your emails 3. Clear your inbox.
  90. 119.
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    4 Fun Ways to Make Your Emails Stand Out 1.

    Customize your mobile signature.
  92. 122.

    ❌Sent via my iPhone ❌Get Outlook for iOS ✓ Sent

    with thumbs; please excuse brvtyand types ✓ iPhone. iTypos. iApologize. ✓ Dictated via Siri —please blame typos on her ✓ Sorry to be terse: My phone has little keys and I have fat fingers ✓ Typed with big thumbs on small phone Most People Do This Smart People Do This
  93. 123.

    4 Fun Ways to Make Your Emails Stand Out 1.

    Customize your mobile signature. 2. Treat your out-of-office auto replies as an opportunity.
  94. 124.

    “I’m out of the office with limited access to email.

    I’ll return on January 6. In case of emergency, please call Dwight Schrute, Assistant to the Regional Manager, at (703) 242-3456.” —Michael Scott
  95. 125.

    “I’d like to know where this place is that everyone’s

    going with so-called limited access to email. I’ve been to many places, and there’s been email access at every one of them.” —Tom Readmond
  96. 127.

    I’m currently out of the office. I look forward to

    responding to your email when I return on January 6. In the meantime, I’d like to share this article on tricksthat can help you get the most out of Dunder Mifflin Infinity. (Number four has saved me tons of time.) I’m attending a conference in New York. My hope is that I’ll bring back ideas and tools that’ll make business even better for my clients. So I can focus on the event, I won’t be responding to emails until I return, on January 6. If you need something before then, please email my colleague, Kelly Kapoor. (She’s super slowbusy, so please give her at least five business days to reply.) Recommend an Article Describe Your Absence
  97. 128.

    Be Candid Be Funny Hello from Jamaica, where I’m on

    vacation. I could tell you I won’t be checking email, but we both know that’s not true: My BlackBerry is rarely more than five feet away. But I’d like to unplug as much as possible, so here’s the deal: If you need to reach me right now, email me back. I’ll tell my family I need a few minutes to return a call. But if it’s not urgent, I promise to get back to you when I’m back in the office on 1/6/2019. A recent study found that vacays can boost performance; relaxation is restorative. This calls for further research! I’ll be out of the office until January 6.
  98. 129.

    4 Fun Ways to Make Your Emails Stand Out 1.

    Customize your mobile signature. 2. Treat your out-of-office auto replies as an opportunity. 3. Write your disclaimer in plain language.
  99. 130.

    CONFIDENTIALITY NOTICE: This message and associated attachments are intended for

    the use of the individual or entity to which it is addressed, and may contain information that is privileged, confidential, and exempt from disclosure under applicable law. If you are not the named recipient, please notify the sender immediately and do not disclose the contents to another person, use it for any purpose, or store/copy the information in any medium. BE WARNED: All the information in the email is mine to do with as I please, such as exploit for profit, use as blackmail, and/or quote on my blog. Note: This disclaimer overrides any disclaimer or statement of confidentiality that may be included in your email. Most People Do This Smart People Do This
  100. 131.

    4 Fun Ways to Make Your Emails Stand Out 1.

    Customize your mobile signature. 2. Treat your out-of-office auto replies as an opportunity. 3. Write your disclaimer in plain language. 4. Buy your own domain.
  101. 132.

    • Before asking for computer help, still thinks it’s funny

    to say, “I’m computer illiterate” • Calls you on the phone to tell you about a neat website they’ve discovered, then says into the receiver, “Ok, go to h… t… t… p… colon… slash… slash… w… w… w… dot… • Usually types in ALL CAPS • Sends you email chain letters saying that Bill Gates will eat your hard drive unless you forward this message to everyone you know • Most likely knows their way around a computer • When the Internet stops working, actually tries rebooting the router before calling a family member for help • Good chance they’re skilled and capable • Maybe even a digital consultant @YourName .com
  102. 134.

    3 Everyday Emails That Make You Sound Abrupt or Dismissive

    1. When you use passive-aggressive language.
  103. 135.

    Per my last email… Most People Do This It seems

    we’re miscommunicating. Smart People Do This
  104. 138.

    Actually, I pulled that sentence from our website. Most People

    Do This Good catch. I pulled that sentence from our website. Smart People Do This
  105. 139.

    3 Everyday Emails That Make You Sound Abrupt or Dismissive

    1. When you use passive-aggressive language. 2. When you apologize without sincerity.
  106. 142.

    Sorry, I forgot! Most People Do This I’m so sorry

    —this totally slipped my mind. From now on, I’ll check my calendar first thing in the morning, so this doesn’t happen again. Smart People Do This
  107. 143.

    3 Everyday Emails That Make You Sound Abrupt or Dismissive

    1. When you use passive-aggressive language. 2. When you apologize without sincerity. 3. When you ask without explaining.
  108. 144.

    Would you please send over the distro list for next

    month’s news- letter? Most People Do This
  109. 145.

    Would you please send over the distro list for next

    month’s news- letter? Most People Do This Would you please send over the distro list for next month’s news- letter? I’d like to double-check a few names. Smart People Do This
  110. 149.

    ❌I’m crazy busy right now. Let’s reconnect in a couple

    of weeks. ❌Let me get back to you. ✓ I think what you’re doing is important, and I wish I could help, but I just don’t have the time. ✓ Thanks, but I need to pass on this. Most People Do This Smart People Do This
  111. 150.

    You know David Wallace, right? He’s organizing a conference this

    fall at which I’d like to speak. The last time I contacted him, he suggested that I attend (which I’d have to pay to do). But I’m interested in getting hired. Do you think I should follow-up, or is David focused on putting butts in seats? Thanks for your candid guidance. In fact, David and I do a fair amount of business together. Which means I can guarantee that his interest, at this point, is in putting butts in seats, as you put it. And since you and I are friends, I can tell you in plain language that it is highly unlikely he is going to book you as a speaker for this in the future. You and I know that anything can happen, but this is not where I would invest my time if I were you. What I Once Asked a Friend What He Wrote Back
  112. 151.

    3 Rookie Mistakes We’ve All Made With Email 1. Providing

    false hope. 2. Asking for something without providing an out.
  113. 152.

    From: Erin To: Deangelo Subject: My Annual Raise Dear Deangelo,

    Welcome to Dunder Mifflin! I was disappointed that I didn’t get a raise last year, and so I’d welcome the chance to talk with you, my new manager, to make sure I’m on the right track for this year.
  114. 153.

    Ask #1 Please let me know when you’re available for

    a meeting. Ask #3 Might we possibly chat? I’m available in what- ever way is easiest for you: Coffee, lunch, your office, even over cake in the conference room. If you don’t have time, I understand. Ask #2 Can we chat? I’m available in what- ever way is easiest for you: Coffee, lunch, your office, even over cake in the conference room. What do you think?
  115. 154.

    3 Rookie Mistakes That We’ve All Made With Email 1.

    Providing false hope. 2. Asking for something without providing an out. 3. Asking a question that you can answer yourself. This is how you can tell who’s destined to climb the ranks, and who’ll stagnate.
  116. 156.

    Hi Bill, So sorry about this, but I don’t know

    what BCRA is. Can you clarify? Most People Do This Hi Bill, The following senators voted “yes” for the Bipartisan Campaign Reform Act (otherwise known as McCain- Feingold): 1. Akaka (D-HI) 2. Baucus (D-MT) 3. Bayh (D-IN) 4. Biden (D-DE) 5. Bingaman (D-NM) 6. Boxer (D-CA) 7. Byrd (D-WV) Smart People Do This