Why Email Writing Matters – And How You Can Master It! was originally published on Break Into Tech.

Does writing matter?

Writing is dead. In this age of Instagram, Skype, and Snapchat, nothing could be less cool, less relevant to getting ahead. The written word is officially obsolete. Or is it?

Imagine that you’re the boss. And you’re hiring a graphic designer for your hot new startup. Writing is #75 on your list of the Top 3 Criteria. Clearly, it’s cutting-edge visual skills that matter. That’s when you check your Gmail and see emails from two candidates:

Candidate A

I’ve been a huge fan of Zync ever since you launched. And so when I saw that you’re hiring for a graphic designer, I couldn’t help but reach out. You see, design isn’t just my occupation, it’s also my passion. Thus, the chance to apply that passion for an organization that’s changing the world would be a dream come true.

That said, would you be interested in joining me for coffee downtown next week? I know you must be incredibly busy as things ramp up but I’d love to learn more about what you’re looking for and share some ideas I have for the business. If you can’t make it, no worries – and thanks for your consideration!

Candidate B

Just saw the designer job and really want to apply. I’ve got an awesome portfolio that will blow you AWAY. When can I come by to show you my stuff?

Pretty clear who you’re going to interview, right? No need to waste more time on this example – writing matters, blah, blah, blah. But hold on… what if Candidate B’s portfolio really is awesome – way more impressive than Candidate A’s, in fact? It’s just too bad you’ll never, ever see it. Now that’s the power of writing.

We’re not going to argue that you should be good at writing for all the reasons your English teacher talked about – composing essays, diagramming sentences, writing book reports. Nope. The reason that writing matters is because it represents you. It’s like your own personal ambassador that goes ahead of you, striking up conversations on your behalf with your boss, colleagues, and even people that might want to hire you.

Good writing is the smoothest wingman you can imagine. He whispers sweet nothings in people’s ears, tells them how amazing you are, leaves them wanting more. By the time good writing’s done, people can’t wait to meet you.

Bad writing, on the other hand, is your spaz younger brother. Just when you’ve got something good going on with your hot date, he comes running into the room and knocks over your carefully-selected vase of flowers. The mood is ruined, the date is over.

Thus, no matter how tempting it is to skimp on writing (“No one’s gonna read this anyway, right?”), just remember: Writing represents you. Writing is you. And you definitely don’t want to be a spaz.

How to get good at writing

OK, so writing still matters. But how do you get good at it? Especially if you spent 16 years of English class doing more doodling than writing???

Good news: There are two kinds of writing on the job. And the only one that really matters can be mastered immediately.

Two kinds of writing

Chances are, you’re already pretty familiar with the two kinds of writing most employees have to do:

• Writing for Communication

• Writing for Analysis

You’ve been writing for communication your whole life – texting your friends, writing notes to your parents, posting updates on Facebook.

And you’ve been writing for analysis ever since you got to school – book reports, lab write-ups, final exams scribbled into those awesome blue books.

But chances are that you’ve always thought about these two types of writing like this:

1. Writing for Analysis – “If I don’t ace this final report, I’m screwed.”

2. Writing for Communication – “Good thing Messenger has autocorrect since I’ve got 27 chats open at once…”

Well, guess what? The vast majority of jobs are exactly the opposite. Sure, you may have to submit reports once in a while – but they’ll usually just end up gathering digital dust on the company’s network. What really counts are the 227 written communications you sent out today. Who did they influence? Who did they piss off? And, most importantly, how did they make you appear to your colleagues.

Make no mistake, unless your job is in research or journalism, the writing you do to communicate will be, by far, the most important writing you do in your career.

Wait, I actually need to check my email?

As if that’s not crazy enough, get this: When we talk about written communication, what we’re really talking about is email. Yes, the same thing that you thought only your grandma still used is the very thing that the working world runs on.

Consider this: Businesses send over 100 billion emails daily. As in – Every. Single. Day. Meanwhile, it takes the entire world a full year just to send 145 billion texts.

But why? Why would organizations still rely upon such an antiquated technology in this golden age of Twitter, IM, and text? The answer has to do with two critical differences between work and school:

 

School

Work

Collaboration

Mostly frowned upon – “keep your eyes on your own test” is the mantra!

Next to godliness – “did you get feedback on this?” is the key question

Availability

“Any time, all the time” – text with friends all day and expect an immediate response

“If I can squeeze it in between meetings” – send an email and expect a response within 48 hours

Because work requires you both to collaborate closely with others but also to be patient in getting a response (since, unlike at school, everyone’s schedule is full and inflexible), email is the perfect vehicle. It allows you to get others involved when you need them AND lets them respond when they’re available. Which is why everyone from your boss to the CEO will do the vast majority of their communication through it – and expect you to do the same.

In other words, if you’ve only been using your email address to sign up for new sites and humor your professors, get ready to kick things into overdrive the minute you snag your first cubicle!

Who’s your audience?

So, you’ve bit the bullet and loaded up Outlook, ready to rock your first work email. How do you actually do it right?

First, you’ve got to know your audience. As with the opening example, email perception is all in the eye of the recipient. So start by understanding how that person thinks.

Luckily, there are really just three types of audience:

• Internal – Familiar

  • Example: Your boss, your teammates

• Internal – Unfamiliar

  • Example: Someone on another team, a senior leader

• External

  • Example: A vendor, a prospective client

Internal – Familiar

Familiar internal folks will likely receive the bulk of your email communication. You’ll be contacting them to let them know about the status of your projects, ask for feedback, and get buy-in for your ideas. And, unsurprisingly, you should make your communication familiar. This basically means finding the right balance between super formal (remember those stodgy business letters you learned to write in school? – AKA “Dear Sir or Madam…”) and super informal (a quick text to your BFF – AKA “ROFL”). Here’s an example of an email you might send your boss:

Hi Mike,

I just finished up the PR agency search you asked me to complete and I think I’ve found the perfect one: Heathrow. They’ve got a deep background in our space and stellar references from Dinesh and Jane.

As such, I recommend that we schedule a conversation with them for next week so we can confirm that they’re a good fit. Just let me know if you agree and I’ll get that set up.

Thanks!
-Olga

Note that the email opens with a salutation (as opposed to just diving right in) – but it’s a relaxed and friendly one. It then gets right to business (no need to provide lots of context for someone who you talk to everyday) and makes a specific ask (as much as email is used, no one loves a message that doesn’t have a point). And it closes with a note of appreciation – but again, in an informal, friendly way.

Unless you work for the .01% of bosses who still compose official memos on typewriters for circulation through the pneumatic tube system, this is now the standard way to talk to your team in the workplace. Anything more or less formal just feels weird.

Internal – Unfamiliar

But what if you need to write to the big boss? You know, the top dog whose mere shadow makes you scurry in the opposite direction. How can you possibly send a worthy message to a person you’d be afraid to talk to in-person?

Surprise! It’s actually not that different than writing to your own boss. Sure, you may want to upgrade the formality just a smidge, as well as provide some more context, but ultimately, most organizations no longer require that all executive communication be stuffy and brown-nosing. Instead of needing an ego trip every time they open their inboxes, today’s execs just need more time. And you can help with that by sending a tight, clear message.

To illustrate, here’s an email your boss might ask you to write to the CEO during your search for a PR agency:

Dear Luisa,

Mike Xu asked me to send you an update on our PR agency search: After vetting several different firms, we’d like to establish a contract with Heathrow. Not only were they heavily recommended by some of our peers in this space, but when we met with them last week, they proposed an initial plan that was perfectly aligned with our values and way of doing business.

That said, please let me know if you have any reservations about this deal by the end of the week. If not, we’ll move ahead with an exciting new partnership on Monday.

All the best,
Olga

As mentioned, this email is ultimately quite similar to the one you sent your own boss – it’s relatively informal, it’s focused on the task at hand, and it makes a clear ask. The only real differences are that it’s slightly less familiar (presuming that you aren’t on a “Hi” basis with the CEO yet), it gives some more context (since she’s likely less-informed about this project than your manager), and it’s very clear about timelines (since executives are incredibly busy and need guidance in prioritizing their time). Other than that, think of emailing an executive as less like a formal, sweat-inducing exercise in sucking-up and more like a chance to help them wield their expertise wisely – while you get to look super organized and thoughtful along the way!

External

Lastly, how do you approach emailing someone outside the organization? Does the fact that they’re not part of your chain of command necessitate an email that’s more formal or less formal?

While it might be enticing to ramp down the formality for an external party, especially if you’re in a position of power (as in our example of hiring a PR agency), resist the temptation! Just because they can’t fire you doesn’t mean the email can’t come back to those who can. Indeed, some of the hairiest situations we’ve found ourselves in have started with a 3rd party emailing an executive about something they didn’t like. And trust us, no CEO likes to hear about something wrong at the company from the outside.

Besides, emailing outside the organization isn’t about getting to boss someone around. Instead, it’s really about a chance to represent your organization, to make it shine in the eyes of someone just finding out about it. Because when your organization shines, you know some of that UV goodness will reflect back on you. So slather on some sunblock and check out this example of a great external email:

Dear Ted,

It’s my pleasure to let you know that we’ve selected Heathrow as our new PR agency. I can’t thank you and your team enough for taking the time to put together a blockbuster presentation. It got everyone from my colleagues all the way to the CEO excited about this new campaign.

So here’s to the beginning of an amazing new partnership. And look for a calendar invite next week for our kick-off call.

All the best,
Olga

Again, we’ve kept the formality bar relatively high here – not only because we may know a 3rd party less well than our own teammates but also out of respect to the other organization and its work. We’ve also ramped up the positivity. This reflects well on our own organization and it greases the wheels for a strong partnership. If we expect this agency to work nights and weekends to deliver the best ideas, they have to like working with us. And what better way to kick off a new friendship than through some genuine appreciation?

What’s your goal?

Knowing your audience is a great place to start any email. But you also need to know why you’re sending it in the first place if you hope to get the most out of your communication. That way, you can craft the message so that the recipient can’t help but follow-through on what you need – vs. sending it, along with your career, to the Deleted Items folder!

There are basically three reasons to send an email:

• To provide an update – AKA “The FYI”

• To engage in a conversation – AKA “The Contribution”

• To request something – AKA “The Ask”

The FYI

The email sent to provide an update seems like the easiest on the surface. After all, how hard could it be just to say something? The truth is that this kind of email can easily go awry because of mismatched expectations.

Here’s an example: We once worked with a guy who was extremely nice. We’re talking Adopting-Foster-Puppies Nice. But the trouble with being extremely nice, especially as it pertains to email, is that it can feel uncomfortable to deliver a message that’s clear and firm. Doing so could potentially lead to hurt feelings if the clear, firm message isn’t what people want to hear. And so our extremely nice colleague sent out an email like this at the end of a long design project:

Hi everyone,

Here are our final poster designs. We’ve worked really hard to get these right. And they’ve been approved by all the key stakeholders. But if you have any feedback, just let me know!

Thanks!!!
-Extremely Nice Guy

Super nice, right? But can you see where he went wrong? The first three sentences are all pretty clear – after significant toil and struggle, these designs are finally DONE. But then, with one little firmness slip-up, he completely undercuts that message by creating an opening for people to disagree. And sure enough, emboldened by this last sentence, disagree they did, leading to three more weeks of fruitless back-and-forth on a project that was already complete. Which, in turn, led to more hurt feelings than just being 100% clear and firm up-front.

Thus, save yourself this drama by keeping your FYI emails completely clear and firm. Here’s what our colleague should have said:

Subject: FYI – Final Poster Designs

Hi everyone,

Just a quick FYI: Here are the final poster designs. They’ve been approved by all they key stakeholders after a full review process. And we’ll be launching these next week.

All the best,
Extremely Nice Guy

In this version, not only do we remove the final offending sentence but we also use those three magic letters in the subject line and body to be extra clear: This is For Your Information – not your feedback. Clear, firm, and delivered – mission accomplished.

The Contribution

The next type of email – joining an email discussion – can be equally treacherous. Imagine the most flaming, troll-baiting conversation you’ve seen at the bottom of any web article. Now imagine that same conversation happening over email – except that instead of anonymous Internet trolls, the participants are your boss and colleagues. Hazardous waters ahead, sailor!

The way to steer clear of those perilous shoals is to have a clear sense of what you want to achieve before you dive in. While it can be tempting to plunge in headfirst with a passionate appeal or juicy retort, ask yourself if that will help your team accomplish its goal: Reaching a smart decision.

In 99% of cases, the following model will get you closer to that goal, no matter how inspired your wit may be:

• Show respect

• Frame around the desired outcome

• Propose a win-win solution

Here’s how it worked in a real example from our time at LinkedIn. We had just released a new video to our target audience and the head of our team wasn’t happy, as evidenced by the following email:

Subject: Unacceptable

I can’t believe what I’m seeing. Our team’s first video and our products aren’t even in it. What were you thinking??? We need to make a new version immediately.

Big Boss

Ouch! Not exactly a great day at the office. But it definitely got Jeremy’s blood boiling. So much so that he was raring to send the following response:

Dear Big Boss,

I completely disagree. The new video is exactly what we needed – it’s based on research that our users want to focus on results (not products), it’s easily the coolest video that the company has ever made (the whole executive team agrees), and it’s already gotten over a million views (how many 1MM+ videos have you made?).

Case closed,
Jeremy

While this message might have been factually correct, would it have advanced the team’s goal of coming to a good decision? Clearly, no – it doesn’t take much of an imagination to conjure up the team leader’s likely fiery response. And things would only have spiraled further out of control from there. As such, Jeremy ended up using the Respect-Frame-Propose model instead:

Dear Big Boss,

Thanks for your feedback. You know this audience well so I definitely respect your perspective here.

That said, given that our common goal is to drive visits to our new products, why don’t we do this:

1. Let’s give the video a month to measure initial progress towards our goal

2. If, after a month, we’re not getting the results we need, we’ll revisit our strategy and figure out how we can incorporate more product footage

I’ll schedule a meeting for us to review progress next month.

Sounds fair?
-Jeremy

Did this message give Jeremy the smug, self-satisfaction of sending out a brilliant zinger? No. But it also didn’t send him and the team into an endless loop of debate and acrimony. Here’s why, point-by-point:

• Show respect – By acknowledging the leader’s expertise right away, it defused tension and made her feel heard

• Frame around the desired outcome – Instead of debating creative strategy, for which there’s never one right answer, the message brought the conversation back to the common, measurable ground that united the team

• Propose a win-win solution – Just as with any negotiation, trying to claim 100% victory will only leave the other party feeling betrayed; so this message puts forth a plan that allows both parties to have their opinions valued and evaluated fairly

Just as with the FYI email, the Contribution email hinges upon always coming back to your objective. Use that as your North Star and you won’t find yourself adrift in the rocky sea of email!

The Ask

Last but not least is the email that makes a request. It could be that you need a colleague to do a favor, a boss to grant you permission, or feedback on your latest project – but whatever the case, the Ask email needs to be done graciously but definitively.

This can feel like a tricky balance at first. How do you both stroke someone’s ego but also issue a clear request? Truth be told, it’s incredibly easy to veer too far in either direction.

For example, many new grads will send us emails like this:

Dear Omar,

I’m a huge fan of your team at LinkedIn. I just love everything you guys do and really want to know more about your work. I hope we can talk about it some time!

Thanks so much!!!
-Gracious Newbie Colleague

While Omar is as generous a guy as anyone, he’s also incredibly busy. So even though this email is certainly gracious, it’s lack of a definitive request puts an extra burden on him. In fact, it puts five extra burdens on him:

1. He needs to figure out who this person is

2. He needs to figure out whether it’s worth his time to meet with her

3. If he does want to meet with her, he needs to look up his schedule

4. Then, he needs to look up her schedule

5. Finally, he needs to propose a time for them to meet

Again, a lot of work for a guy who’s already swamped!

Still, as weak sauce as that email is, it still comes off better than the opposite version that he receives from time-to-time:

Hey Omar,

I’m a new employee at LinkedIn and I’m going to be in Mountain View this afternoon. Can you please meet me at 3 PM so that you can tell me about your team and how I can get a job on it someday?

Thanks,
Annoying Newbie Colleague

OK, gotta give this guy props for at least being definitive about what he wants. But, seriously? Is this the best you can do after 16 years of formal education? Omar’s no three-piece suit CEO but doesn’t he at least deserve a little respect before he takes time away from his work and family to help you get your next job?

Clearly, the one true path to Ask email success combines the best of both messages – the gratitude of the first with the definitive request of the second.

Here’s what that looks like in the best new grad email we’ve ever received:

Dear Jeremy,

I recently joined LinkedIn after graduating from the University of Michigan (Go Blue!) and was blown away to discover that we have a whole team focused on education. As someone whose goal in life is to help students find their dream careers, I’d love to learn more about your work and get your advice on how to make an impact in this space.

That said, I know you must be extremely busy with all the new products these days, so if you don’t have time to meet, no worries! However, if you’re free at 3 next Wednesday, I’d love to chat for 15 minutes. And I can even share some tips on the latest campus trends, if that’s useful to you.

Thanks for considering!
-Baller Newbie Colleague

This email just crushes the key points:

• Gracious – She shows respect for Jeremy’s expertise (who doesn’t love giving advice?) and time (requesting only the bare minimum and also giving him an easy out)

• Definitive – At the same time, she also makes a very clear ask (3 PM next Wednesday), complete with agenda

But it also gets bonus points for forging a connection (you don’t always have to find something in common with people, though LinkedIn makes it so easy that it’s a waste not to look) and even offering something in return.

The result? Not only did Jeremy take the initial meeting, but this Newbie is now on his radar for future jobs with the team!

So just like with the other two categories of email, it pays to know what you want to achieve with your Ask and then align every part of your message to reach that goal.

Five Email Traps

So now you know why writing matters. You know why email is the writing format of choice at work. And why it’s critical to know who and what you’re writing for. Time to get typing, right?

Wrong.

Email giveth but email also taketh away. For every workplace email that’s unified a team or gotten something done, there are 10 others that started a crisis where there was none before or even got someone fired. Thus, before you step up to the big leagues of writing, check out these five email traps:

Trap 1: Writing Too Much

The most common email sin committed by new grads is, strangely enough, writing too much. You’d think a generation raised on emoticons and GChat would have the opposite problem. But there’s just something about the blank canvas of an open email window that seems to invite “word spew.”

Early on in his career, Omar’s particular specialty was the Thesis Email. He figured that if he could just lay out his full case – assumptions, followed by hypotheses, followed by the pros and cons of every possible side, followed by a painstaking journey to the definitive TRUTH – he could win every argument and win over his colleagues in the process. And, naturally, the exact opposite happened: People just stopped reading his emails. The CEO of his nonprofit even called him into his office to lay it out like this: “Omar, people are busy. Your emails are just too long.”

Things have only gotten worse in the years since. As more and more email goes out – and more and more email is read on tiny mobile screens – people’s tolerance for lengthy messages has just gone down and down.

So, instead of dumping the genius, encyclopedic contents of your brain into your next email, do this instead:

• Apply the 5-Second Test: Is your opening sentence so clear and relevant to the recipient that they should bother to read the rest of it? Remember, on a phone screen, this might be the only part that shows up at first.

• Cap at 3 Paragraphs: Even if your first sentence is worthy of Hemingway, don’t assume this grants you the privilege to then drone on in a scattered way for the rest of the email. Keep it to three paragraphs or about 30 seconds of reading.

• Attach, In Case of Emergency: If you absolutely must include more than a couple of paragraphs of information, put it in an attachment. Just recognize that your file may not get read, so make the body text work as hard as possible.

Trap 2: Sending Sensitive/Embarrassing Information

While email is an incredibly effective tool for communicating with both internal and external parties, it’s also an incredibly effective tool for taking internal information and making it external. In fact, not a week goes by where the press doesn’t publish a secret internal document from some industry that was leaked via… guess what… email.

Thus, while it’s certainly OK to discuss internal projects over email, just use this rule of thumb when you run into dilemmas about what’s not OK: Would I be comfortable if this got seen by the CEO, a competitor, or the media?

In other words, reviewing the latest design from your art team is usually totally fine. But sending out the complete blueprint for a top-secret new smartphone might not be wise.

This also goes for comporting yourself well over email. Even if there’s not a byte of sensitive company data in your ardent letter to your secret admirer or your flame war with your arch-nemesis in the nearby cube, apply the same recipient test – and maybe even throw in your mom for good measure!

Note that some organizations are even more strict here. When Omar worked at Apple – a notorious bastion of secrecy in a highly secretive industry – he almost got fired for sending notes from a meeting to his teammates! While this may sound draconian, every organization’s approach is different. So when in doubt, ask.

Trap 3: Making a Mess of Emotions

Email is a technical marvel. Just think about it: A deposed Nigerian prince can now let everyone in the world have a chance at his oil fortune within seconds – and collect bank account numbers from every continent just as quickly. But the one thing that technology has never been able to solve as well as a face-to-face conversation is conveying emotion. Even with the advent of emoticons, it can be all too easy to misinterpret a written message and turn a molehill into a mountain of e-agony!

Just check out this example:

Hi Jeremy,

Just got the invoice from the agency. Very funny. Come see me in my office right away.

-Your Boss

How should I respond to this? Was the invoice ha-ha funny or “I can’t believe you spent this much money” funny? Do I need to come to the office right away so that we can laugh about it together or so that you can fire me?

And that’s exactly the problem with email. You just don’t know, do you?

So Rule #1 of email and emotion is to assume good intentions and then clarify. While it’s all too easy to presume the worst, that often just leads to sending off your own angry email, making everything even worse. Thus, start by putting an imaginary “” at the end of each ambiguous sentence and follow-up to confirm. For example:

Hi Boss,

Thanks for letting me know! Just to confirm – was there a problem with the invoice? If so, I’ll investigate and come meet you with full details.

All the best,
Jeremy

OK, now that you’ve defused a potentially lethal email bomb, Rule #2 is to avoid sending over your own emotionally charged message. You can do this by avoiding conveying negative emotions over email and then removing ambiguity wherever possible.

Take this email to one of our direct reports:

Hi Rising Star,

I can’t say I’m too happy with the final report. This whole thing kind of reminds me of the Titanic.

-Jeremy

Look at that – Jeremy’s already made a hash of the whole situation in just two lines! First, he jumped right into criticism – a sure-fire way to put someone on the defensive, especially because they don’t have the ability to respond in real-time (remember, it’s an email). And then, to make matters worse, he tried to make light of the situation; but that’s not clear at all when you reference the most doomed voyage in world history without context.

What he should have done was save any negative feedback for an in-person conversation, where both parties could make their points without electronic interference. And then he should have worked extra hard to make the levity clear. Something like this would have been more appropriate:

Hi Rising Star,

I was just looking at the final report and would love to review it with you soon – will put something on the calendar. In the meantime, just know that I appreciate what a HUGE project this was. I mean, it was less like sailing the Titanic than sailing the iceberg! 🙂

All the best,
Jeremy

No doubt, pulling off this delicate dance of emotions in email isn’t easy. But the hard work is well worth the great work friendships you’ll preserve by doing so. Trust us on this one!

PS: And yes, basic emoticons (so no 0>o0 snowmen or anything) are legit in most offices since they really do help to warm up what can often be a chilly medium. As always though, when in doubt, ask around!

Trap 4: Text-Speak (You Knew It Was Coming!)

No sooner did we make an impassioned defense of emoticons than we’re back to burst your bubble: When you go to the office, leave the text-speak at home.

We know, we know. It’s a cliché to assume that new grads all LOL, ROFL, “i c u” and such. Or that they can’t tell the difference between a personal message and one to the CEO.

But we wouldn’t be responsible stewards of the keys to the office kingdom if we didn’t bring it up – because, sad to say, we’ve seen it time and again.

For instance, Jeremy’s wife briefly taught college-level history courses and was intrigued to see this in a report: “George Washington was America’s #1 prez.” So you can imagine what the emails in that class looked like.

That said, we know you, our enlightened reader, would never do such a thing, so we won’t belabor the point. Just be sure to pass the word onto your less-enlightened friends!

Trap 5: Blowing the Timing

Email is a funny thing when it comes to timing. We’ve already told you that its very asynchronicity is what makes it so useful (i.e., you don’t have to respond right away, like with IM, so it fits the workplace schedule). And yet, people have strong feelings about when you should respond and when they should respond (usually faster for the former, slower for the latter, naturally). So here’s how to navigate this tricky temporal terrain.

When you receive an email, the general rule of thumb is to respond in 24 hours. Again, each office is different, but this usually means:

• You probably want to check your Inbox at least a couple of times a day.

• If you get an email that you won’t be able to fully respond to for more than 24 hours (e.g., you’re waiting on a piece of information that will arrive next week, you don’t have time to complete the requested task today), send a courtesy response letting the sender know you’ve received the message and when you expect to complete the full request. Waiting in Email Purgatory sucks because the other person often has their own deadlines they’re trying to meet, so don’t be the Dante of Email.

• If you’ll be unable to respond to email at all for more than 24 hours (e.g., you’re on vacation or will be fully booked on a business trip), you should definitely set-up an Out of Office message that sets clear expectations (“I’ll get back to you by Friday”) and also gives an immediate back-up plan (“Contact Sheena for urgent requests”).

• Note: The 24-hour window doesn’t apply to projects where there’s a clear expectation that you’ll respond faster. For example, if your colleague is organizing a big event at the end of the day, don’t be that guy who responds the next morning with “I got back to you within 24 hours, didn’t I?” Just don’t.

When you send an email, the following rules apply:

• Assume it will take at least 24 hours to get a response. While you can always pull the “It’s an emergency!” card when it’s a genuine emergency, pull it one too many times and you’ll be the Boy Who Emailed Wolf.

• Don’t assume you will get a response in 24 hours unless you specifically ask for it. If you really need something done by tomorrow, put the deadline in the subject line like this: Send Final Report. And then add it to the body in bold: Please send me the final report by 5 PM on Wednesday.

• It’s OK to follow-up if you don’t hear back in the timeframe requested. The best way to do so is the following:

  • Use a service like FollowUpThen.com to add a reminder to the Bcc line. Basically, it boomerangs the email back to your Inbox on the desired date to remind you to follow-up.

  • Then, Reply All to the first email you sent, which opens up a new message to the delinquent respondent with the time-stamped original below. Usually, the combination of a simple “Just following-up here – would love your thoughts!” with the evidence of their delinquency is enough to wring a response out of them!

As with much in life, you only get what you ask for – and follow-up on! So start by putting good email karma out there with swift responses of your own. And then, if you need a response from someone else, be clear about what you need.

So there you have it, more writing about writing than you ever thought mattered. But if the business world is going to send 100 billion emails every day, you might as well make yours count. And now you can.

So go forth and write, letting your suave email wingmen pave the way for success within your organization and beyond!

Email Cheat Sheet

• Writing matters because people judge you based on it – when you send them an organized message, they’ll think you’re organized. In other words, when it comes to the workplace, you are what you write.

• The most important writing you’ll do in the vast majority of jobs is email. You’ll spend more time emailing with many people than talking face-to-face, so this is your best chance to make a great impression.

• When you sit down to write an email, the first thing to keep in mind is how the audience affects the tone. In general, you can strike a more informal tone with those you work with everyday than new acquaintances inside and outside the company.

• The next thing you should consider is the point of the email and how that relates to the content:

  • Providing an update – Keep it short and simple; this is an FYI, not an invitation to an email debate

  • Joining a conversation – Be respectful, focus on the goal, and come up with win-win solutions; don’t start a flame war

  • Asking for something – Open graciously but make a clear ask; don’t leave the recipient to do all the work

• As much fun as all this writing can be, watch out for five email traps:

  • Writing too much – Woah, Charles Dickens! You’re not getting paid by the word, you’re getting paid to cut to the chase.

  • Sending sensitive info – Don’t send anything over email that you wouldn’t be comfortable having published in a newspaper (because it’s definitely happened before!)

  • Ignoring emotions – Email can come off as very vague so be clear about you mean, lest the recipient assume the worst

  • Emailing a text – Keep text-speak on your phone and professional language in your emails. Period.

  • Screwing up the timing – The best thing about email (the fact that you can get to it whenever you want) is also the worst: No one likes waiting around for an email deadbeat. So send timely responses and let people know when you need a response back.

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