173: Writing Better Emails with Leslie O’Flahavan

Pete Mockaitis
Leslie, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Leslie O’Flahavan
Thank you for having me.

Pete Mockaitis
Well, I got a real kick out of something that you shared, which was that your husband and you were born on the same day, December 3^rd. That happens to also be the day I was married. So that’s wild – 1-2-3, it shows up a lot. How do you and your husband celebrate or navigate this interesting fact you share?

Leslie O’Flahavan
Well, going forward we will celebrate it by commemorating your anniversary.

Pete Mockaitis
Oh, thank you!

Leslie O’Flahavan
Well, I think I also let you know that our best friend, or my best friend is also born on December 3^rd, so for a long time we’ve celebrated our birthday by having my best friend’s husband prepare us a beautiful meal, and he’s a wonderful cook. One time he made homemade lobster stuffed ravioli. So three of us were dining on our birthday and one friend was just working really hard. But things are gloomy for us because those friends are moving to California, so we’ll have to develop a new tradition.

Pete Mockaitis
That’s tricky. Is it worth moving right along with them to keep the ravioli going?

Leslie O’Flahavan
Yes, I think it is. They’re moving to Sonoma County, so I think there will be great wine with the ravioli now.

Pete Mockaitis
Oh, it sounds breathtaking. I’m imagining the scenery as well.

Leslie O’Flahavan
Right, right.

Pete Mockaitis
Well, I am intrigued to dig into your wisdom here. You’ve got a whole course about writing emails which is, I think, fantastic, because we do it all the time, but I don’t know how many folks really have invested the time, thought, energy to invest in enriching that skill, though it seems like something that we probably should. Probably like typing too – we do a lot of that, until I guess the robot speech transcription is up and running. So, could you maybe orient us first and foremost, when it comes to thinking about emails as a communication channel, when is it right to use email, versus are we using email too much?

Leslie O’Flahavan
Yes, I think we probably are using email too much, and I think every day when we come in and open our emails and look at our inboxes and our shoulders just slump. We don’t feel like reading and we don’t feel like writing; we know that everyone else is using email too much too. But I think you’re asking me a more specific question than that one; you’re asking I think when is it right to use email and when is it not right to use email.

Pete Mockaitis
Right.

Leslie O’Flahavan
So I have a couple of answers to that.

So, email’s great when you have to continue something that already has momentum. So if you and a colleague are working on a project, it’s great to use email to confirm deadlines, because the project has its own momentum; or to list out tasks, because you’ve probably discussed those already and email’s a good way to keep things going.

Email’s not such a good way to overcome resistance. In fact, it’s a pretty bad way to overcome resistance. So if you have a topic you need to communicate with someone about, and you know they’re not going to like it – they don’t agree with you, they don’t want to do that – then email is not going to work as well. It’s just not so good for overcoming resistance, it’s not good for changing people’s minds. Even if they don’t disagree with you – if they just have another idea, email’s not very good for changing people’s minds. And email’s really not good when you’re walking on eggshells with the person you’re writing to. If the situation is fraught or if the topic needs to be handled very sensitively, email is not the best channel to choose.

Pete Mockaitis
Oh, that’s interesting. It seems like you’re touching upon an implication that’s coming up again and again with guests, which is all of this requires in measure a courage, because those are maybe the exact times where folks might want to shy away from a direct head-to-head, face-to-face exchange, and carefully craft their statements – for the eggshells, and to cover some matters that may be contentious. And you’re saying, “No, no. This is precisely the time to not email.”

Leslie O’Flahavan
Yes, I am saying that, and I realize that I’m giving advice that some people will just not take, but at least I want to think about it this way. It’s rarely a case where you have to choose an in-person meeting or a telephone call, or an email; that you can’t do both. Lots of times you can both. It’s a false idea that either I will email you or we’ll meet about this, but we won’t do both. You can easily do both.

And I agree with you – people do wimp out and choose email when they have difficult things to say, because it’s just a little bit less personal, but when they do that, they kind of poke a hole in the bucket of goodwill you need to get along with the people you work with. A little bit of the goodwill drains out when your colleague receives an email from you at 4:59 asking if you can move a deadline up 3 days. You can do it, yeah – you can click “Send”, it’s possible to do it, but it’s really not a very good idea in the long run.

So, culturally I think people in the workplace are far less interested in using the phone now than they were 10 years ago or even 5 years ago, but I think we really still need to remember that song channel that is synchronous, where we’re in it at the same time, even if it’s a video call, that we should remember we should use those personal channels, more personal than email, to handle or lay the groundwork for a follow-up by email.

Pete Mockaitis
Alright, understood. And so, I’m now thinking a little bit about, you mentioned you wanted to use email to continue something, but not so much to start something. So if you’re rolling out a big, cool initiative or introduction, you’d say it’d be best to get folks assembled or to convey that in a more live or synchronous fashion first.

Leslie O’Flahavan
Yes, I agree with that. And I know it’s not always possible to do a conference call, and boy, they have their own baggage, don’t they? Some conference calls are horrible. But it’s another example that it’s not an either / or. You can do a short conference call; if you can’t get everyone in the same time zone, do two or three short conference calls to start something, to kick off, and follow up with email about the logistics, about the responsibilities, about the schedule – that kind of thing. But you can’t build enthusiasm very well via email.

Pete Mockaitis
Okay, very good. Understood, thank you. So now let’s talk about when it does come to email. So we’re going there. You’ve got a couple of perspectives, in terms of not being robotic. So what could you share with us about that game to try to convey a degree of warmth, while also having that consistency, fairness, professionalism and other stuff that we think about, coming from a written modality?

Leslie O’Flahavan
Sure. I think there are physical parts of the email that your readers expect to be a little bit more personal, and other parts of the email that your readers might not mind if they’re copied and pasted. And we usually expect emails to be more personal at the start and at the finish. So, maybe the middle of the email is a copy and paste from your FAQs, or it has some data in it from a report – you didn’t actually handcraft that for that email, but you should handcraft in a personal way the opening and the closing.

And so, the pattern – it’s almost like a conversation. We greet each other personally at the start, the middle of a phone conversation or an in-person conversation may be ideas we’ve shared with others, but we’re sharing with a new person here, and then we wrap up in a personal way. That’s how we should build our emails also. So for the folks who are listening who may think, “Hey, I’m too busy to start my email by writing ‘Dear Fred’”, or “I’m too busy to end my email by writing something like ‘Looking forward to seeing you on Thursday’” – no, you’re not too busy. You should take the time to invest in some personal writing in the physical places in the email where your reader expects that.

Pete Mockaitis
Oh, thank you. And as you share this, that gets me thinking about my own email practice, and I think I do a pretty good job with the opener, like, “Hey, how’s everything going, Arthur? (Episode 6) with imperative and purpose and making it happen. That’s great.” And it’s like, “Oh, I wonder if you can introduce me to this person?” And so then it is kind of formal – “Here’s the story about this person and their context and why I think they would be a great fit and I’d love to be connected.”

And I think I probably drop the ball, as you laid this out, on the closing side. It’s just like, “Hey, thanks so much for your help” is probably what I default to. And you gave a nice example of, “Looking forward to seeing you next Thursday”, but sometimes I’m not seeing them soon. So, could you maybe give us some even word-for-word scripts of some great stuff to include personally at the end of an email, maybe when you don’t actually see that person that often?

Leslie O’Flahavan
Sure. There’s nothing wrong with saying “Thanks for your help.” There’s absolutely nothing wrong with it, and it’s polite and it’s friendly, so you don’t be too hard on yourself about that.

Pete Mockaitis
Okay, thank you, Leslie.

Leslie O’Flahavan
But there are other things you can say. I like a technique of closing by restating the action I’m hoping for out of the email. So, in the example you gave, let’s say you’re asking someone named Fred to introduce you to someone named Sue. You could end your email, “Thanks for your help. I’m looking forward to connecting with Sue.” So that you’re reaffirming what’s coming up; the reason that you wrote, you’re reaffirming it at the end. You put a little sugar in there, “Thanks for your help”, and then you restated your hoped-for outcome. That’s what I like to do at the end. So I could say, “I’m looking forward to speaking with you on Thursday”, or I could say, “I’m looking forward to reviewing that PowerPoint”, if you’ve asked the person to send you a PowerPoint that she used in a presentation. Or, “Thanks for your help. I do need those brochures this week”, something like this.

You take the chance, because you have the reader’s attention at the end. People often scan the beginning and then hop down to the end. They’re looking for a to-do item, but we’re not going to slip into that pattern; we’re not saving the to-do item for the end. No way. But we can put a little bit of sugar at the end so that the closing is personal. Readers really like it when the email comes across as written for them and them only.

Pete Mockaitis
Yes.

Leslie O’Flahavan
So if you end it,”Thanks for your help”, there’s absolutely nothing wrong with that – it’s gracious and it’s polite.

Pete Mockaitis
Alright. And as you share some of those closer examples, sometimes I’ve critiqued my own emails because if you say, “Looking forward to connecting with this person”… I guess sometimes I criticize myself, like, “Oh that’s kind of presumptuous, Pete. You just assume they’re going to say ‘Yes’ and comply with your request.” How do you think about that one?

Leslie O’Flahavan
Well, I can see why you’d be cautious. That just shows that you know words have power and you don’t want them to have power for evil; you want them to have good power. But remember, no little phrase at the end of an email exists in a vacuum; it exists shoulder-to-shoulder with all the other things you wrote in the email. So if your email was really presumptuous all along, if you’re like, “Hi, I want to meet her. She could really advance my career. I don’t know you very well, but I know you can help me get to meet this other person I do care about”, then the end of your email will sound presumptuous. But if you’ve done your homework for the person you’re actually emailing and you’ve explained why you’d like to be given the gift of this connection, then at the end you’re just reaffirming what you want, not trying to get over.

Pete Mockaitis
Oh, that’s good. That’s good. And sometimes I’ll include in there, “Hey, thanks so much for considering this request.” It just gives a little emphasis that I’m not presuming that they’re going to say “Yes”, but by having opened and begun reading this email, they’re de facto considering it, and that in and of itself is a gift. It’s a good turn of phrase there – the gift of that introduction. Thank you.

Leslie O’Flahavan
Certainly.

Pete Mockaitis
Well, so then, I’ve got many questions, but let’s maybe just go with, you talked about some of that rapport in the opening and closing. Are there any other pieces we should bear in mind when it comes to some of the rapport, some of the empathy, some of the personal, emotional stuff of the message?

Leslie O’Flahavan
Yes. Just number one, you should do the work to create rapport and you should do the work to show empathy. It’s odd to me how willing people are to monitor their own tone and their own use of words when they’re talking to each other, so that they don’t give offense and so that they show how the other person thinks. We’re quite willing to do this when we talk to each other.

But for some reason, maybe it’s just because we’re overwhelmed by email, we seem to think we don’t have to do it there. People tell me when I do workshops on writing email, they ask me, “How should I handle it when somebody writes me an email and says ‘Thanks’?” And they’re all angry. I say, “Well, you don’t really have to do anything there, but you might want to check your attitude. Why are you angry that someone wrote you an email that says ‘Thanks’?” Well, they’re angry because their inboxes are too full and it’s wearing them out, and they can’t complete the tasks they need to complete from their inbox, and so they’re getting cranky.

But I guess I just want to remind people that rapport is kind of a non-specific feeling of goodwill, and if you don’t do the work to build this feeling of connection via email, then it won’t be there when you need it. So rapport is that goodwill, that magnetism that we have for our colleagues that we draw on when we need help. And so the example I gave earlier – you need your colleague to finish a project 3 days earlier than she thought she was supposed to – you better have built some rapport there. You better have it, ’cause you’re going to make a rapport withdrawal from the bank.

So in your emails you should use the same social courtesies and the awareness of other people that you would use if you were talking to them. When you walk down the corridor at work and you’re heading toward the break room to get some coffee and you pass your colleague, you say, “Hey, how was your weekend?” And you don’t actually always care, but you say it because that’s how people treat each other. And I’m not saying you need to write, “Hey, how was your weekend?” in your email, but you have to realize that if you’re not talking to that person, if you’re emailing instead, you need to take the measures that feel natural to you to build the closeness.

Pete Mockaitis
Alright, thank you. And it’s funny – I’ve noticed a trend in emails that I’ve been getting lately. I don’t know if it’s just me or more and more people seem to be saying, “Happy day of the week”, like “Happy Thursday!” And it’s so funny because in a way that is completely not original or clever or custom to me, but nonetheless it makes me feel good. It’s like, “Why not celebrate Thursday for being Thursday?” I actually appreciate it, kind of like the “How was your weekend?”

Leslie O’Flahavan
Yeah, of course you do. And maybe you think it’s kind of dorky that the person writes “Happy Thursday” or “Happy hump day” or whatever crazy thing they say on Wednesday, and it probably is a little bit dorky, but you give them props for the effort; they made the effort. So, it comes across as pleasant, as charming, and it’s important. There is no right word or wrong word to use to build rapport. Even if you do it in kind of a clunky way or kind of an awkward way, as long as the effort is there the words will sound fine; they’ll have the effect they’re meant to have.

Pete Mockaitis
Alright. And so now I want to talk a little bit about the results, the outcome of a given email. I’d love to get your take on sort of top tips for maximizing the odds that your email will get opened, read, attended to, replied, or complied with in the request. What are the keys that make it happen?

Leslie O’Flahavan
Okay, I’m going to do this one quickly and in a bossy fashion. Number one – you have to have a useful subject line. The subject line is your first and best chance to prepare your reader to behave properly. And you notice I didn’t say the subject line is the best way to get your reader’s attention, because if that were the case we would write things like, “Your blood test results are in”, like spammers write. But the subject line is your first chance to prepare your reader to respond properly.

The next thing you must do to improve the chances that your reader will do what you’ve asked or actually read through the email is use the first two or three lines to write what I and other people call a “BLUF statement”. BLUF stands for “Bottom Line Up Front”. So if you’re asking for something, you start with the request and give the reason for the request later. If you’re updating a project plan, you give a summary of the update right away. The main point, whatever you want to say, goes at the very beginning, you give the bottom line.

People forget where that idiom comes from – Bottom Line Up Front – it comes from the world of accounting, it comes from a ledger. So if you can picture the numbers 3 + 3 + 1 stacked up in a ledger, then you have the bottom line, then you have the number 7. And this writing in principle says, “Please, in email, tell your reader 7; don’t tell your reader 3 + 3 + 1 = 7 in the email.” Write a great subject line and then start with the bottom line; start with what it adds up to right away.

Pete Mockaitis
Now is that after the friendly opener sentence?

Leslie O’Flahavan
Yes, a little bit of sugar – a quarter teaspoon of sugar, I guess. So let’s say you have a problem and a solution. You’re writing an email to your boss, who wants to recruit unpaid interns for summer work. But you know that unless we pay these interns, we’re not going to attract the candidates we want; we’re going to get some kind of halfway good candidates for this internship. You want a paid internship. So you could write a whole paragraph about the problem of unpaid internship, and then you could follow with a paragraph about why we should pay our interns.

And then I’m saying that’s the wrong order. Give the solution first. You can elaborate on it later if you’d like, but give the solution first in your BLUF paragraph, put the bottom line up front. So it’d sound like this – it would say, “Dear Susan, thanks for giving me the background on our internship program for the last 5 years. I’ve done my research and I’m certain that an unpaid internship won’t attract the candidates we need. We need to pay for interns this summer, but I think $2,000 for the full summer will be enough.” That’s the first paragraph; I did it in 3 sentences.

Pete Mockaitis
Got it, thank you. You gave us a few rules. Are there more to get the reply and results you’re looking for?

Leslie O’Flahavan
I’ll add one more rule, one more writing behavior that I think is really important. Many, many people read their work emails on a mobile device now, so that pairing of a very clear subject line followed by a very short and message-oriented BLUF paragraph at the beginning – that pairing is really important.

There’s one other thing you can do for multi-paragraph emails, and that is put a heading above each section so the recipient can scan the email first, before reading it fully. That’s convenient on a mobile device and it’s convenient on every other device that people read emails on. So if you have a two-paragraph email of course you don’t need headings in it, but if you have three paragraphs, you have four paragraphs, really think about adding headings, bolded titles for each section so the reader can see what’s there. It enables the recipient to do a visual inventory and then read the sections of the email as needed.

Pete Mockaitis
Alright. Now, for these headings – boy, my Bain action, implication, slide headlines are coming through. I’m thinking, should that heading ideally be the core idea of the paragraph in one sentence or a label, such as “Timeline”?

Leslie O’Flahavan
Well, my preference is that it would be the core idea of the paragraph, instead of just one label. Because let’s say – taking the example you just gave – “Timeline” – let’s say that you’ve just written a paragraph that says, “The timeline is unreasonable. If we stick to this timeline we won’t be able to do the user testing we should do before we give this product to the client.”

So if you just write “Timeline”, then the reader knows, “Hey, he discussed the timeline in this section”. But if you write “Timeline seams unreasonable” or “Timeline will cause problems” or “Timeline needs to be extended” – any of those three, then the reader gets the message and can dip into the paragraph as needed. It’s perverse but true, that the nicest thing someone can say to you is, “You structured your email so well I did not have to read every single word.”

Pete Mockaitis
Alright. Perverse but true. Hashtag it. [laugh]

Leslie O’Flahavan
Perverse but true. Sounds like a backhanded compliment, but it’s actually high praise. If you have a BLUF paragraph and a clear subject line and headings within a multi-paragraph email, your recipient may be able to skip around. Maybe she already knows the timeline is too ambitious, and so just seeing that you wrote the timeline is too ambitious or the timeline is unreasonable, she’s like, “Yeah, I know. I don’t actually have to read that paragraph.”

Pete Mockaitis
Alright. So you talk about bolding of headers there. I’d love to talk fonts, formatting, italics, colors. Oh my! What are your thoughts in this realm?

Leslie O’Flahavan
Okay, now I want you to picture a very mean-faced, scoldy person with an index finger up ’cause I’m about to lay a scolding down.

Pete Mockaitis
Oh, scold us.

Leslie O’Flahavan
Here we go – black text, white background, no shading, no clip art, no scripture quotes, no animations, no fun colors. Clean, easy to read Sans Serif font, nothing curly, nothing artful. Reading email is a tiresome task so you do everything possible you can do to make it clean, streamlined and easy to see. Black on white, very little use of bold, italics, and never use underline unless you’re hyperlinking. Hyperlinking has taken underlining. Even if your organization’s style is not to underline hyperlinks – maybe they’re just bold or something – still, most people interpret an underlined word as possibly clickable, so you don’t want to use underlining anymore.

I wish I could cite this research properly, so I’m going to probably misquote it here, but there is some usability research that shows that people can understand the intent of two font effects easily; and three or four or five, they kind of lose their way. So here’s an example.

Let’s say you’re writing an email about who’s going to do what after a meeting, you’re sorting out the tasks after a meeting. You could use bold for each person’s name, you could use italics for the deadline for their task, and after that you should stop using font effects, because the people who read the email will get it – bold is for the person who’s doing it, italics is for the deadline for that task. But if you add color also, then the fact that you have three font effects starts to diminish the power of the other two, and the recipient will be kind of like, “Hm, that’s a lot of formatting”, but it’s not as concrete an understanding of what the formatting means.

Pete Mockaitis
Okay, understood. And so, quick follow-ups here. Sans Serif font – so if you’re reading a book, most books have a Serif font. You say we want to be friendly to the eyeball and the Serif kind of draws the eyes across for paragraphs to rock and roll there. But you’re saying Sans Serif is the way to go for an email.

Leslie O’Flahavan
Yes, because emails are more tiring and tiresome to read than anything in print. When you read an email, no matter how large or small the device is, it’s emitting light. And a device that emits light is just harder to read than print ever will be. And as you know if you’re reading on a mobile device, even if the individual letters are the same size font as they would’ve been on a much larger device, you’re seeing so much less information at a time. So online, the Sans Serif fonts are just more streamlined and they’re more modern-looking. I would just stick with those – they’re easier to read online.

Pete Mockaitis
Well, now let’s unleash a ferocious debate amongst the world. Alright – Ariel, Verdana, Helvetica – what’s best? Is there studies, is there research on this?

Leslie O’Flahavan
I really don’t know and my sense is that it really doesn’t matter, and I think that if it’s black on white and it’s large enough, I really don’t think it matters much. It’s when someone is being coy and they’re going with Dutch Blue on a Dove Gray background, that’s the problem. I would just react as a reader – if it’s difficult to read for any reason, I’m not going to take it in as well, I’m not going to understand it. I may open it, close it, plan to get back to it and just not do so.

Pete Mockaitis
Alright. And so for size – 10 point, 12 point, 14 point? Are they all good?

Leslie O’Flahavan
I would go with 12 or larger. It does depend on the font – what looks big in one font at 14 looks really big in another font. So, it depends on the font, and it depends on how middle-aged you are. I’m profoundly middle-aged.

Pete Mockaitis
I think you’d probably go too high. If you’re rocking 36 it’s a little bit like, “What?” So now, this question is the bane of a number of folks’ existence. I know I’m not the only one and I’m not going insane here, ’cause a few people have confirmed that this is some messed up stuff. Alright, let’s talk Gmail. Let’s say you’re typing something into Gmail, you maybe do some copy / pasting from other sources into the Gmail, the Gmail looks totally normal and fine, but then when it’s read on a client like an Outlook or an Apple Mail, there’s wildly inconsistent formatting on the receiver side. It looks kind of busted and unprofessional and frankly I feel deceived and lied to by Gmail, which I love in so many respects, but this one messes with me. Leslie, do you have the Holy Grail for it? Do you know what I’m talking about and do you know the answer?

Leslie O’Flahavan
I do know what you’re talking about. I don’t have the Holy Grail for you, I’m so sorry. I love Gmail second, not first, so my own personal Gmail is like a swamp of ancient emails and I refer my email to Gmail, I don’t read I there first or write it there first.

But I think it’s a big difference if you’re writing to people you know – then I would just go with plain text. Plain text email looks perfectly fine if the purpose is not marketing. Plain text is perfectly fine, especially if you’re composing for plain text. You know it’s not that you had to resort to plain text because HTML wasn’t working, but that you composed in plain text, looks perfectly fine. If you’re writing marketing emails and you’re just like, “Gmail, get yourself straight. I need to make this good-looking email with an image header and a background color and these other things work”, then you probably need to go to Constant Contact or MailChimp or something that will make sure that what you send looks groovy, no matter where it goes.

Pete Mockaitis
I hear you. I guess what gets me is the Gmail looks like it’s all normal and cool, like, “Okay, great”, but in fact it’s not. It’s like they’re hiding something from me in the “Compose” stage. And I’ve heard some people, they just get all of it in a standard font, written elsewhere – on Word or Google Docs or something, and they triple-click it, “Okay, Verdana 12, Verdana 12.” And then copy / paste the whole thing with zero edits in order to ensure that this happens. So, I’m surprised that this is still an issue. I’ve spent more than one hour deep in the Google product forums, trying to get to the bottom of it, and apparently it’s been an issue for years. Maybe in 2018 this will be old news and they’ll say, “What are they even talking about?”

Leslie O’Flahavan
Yeah, I hope so. It sounds really bad. I don’t have first-hand experience with that, as I said, ’cause I’m mostly sending from Outlook, staying in there, as I just stay in Outlook, yeah.

Pete Mockaitis
Okay. And tell me, Leslie – is there anything else you really want to make sure to mention before we hear about your favorite things?

Leslie O’Flahavan
Okay. Well, in my favorite things I’m going to tell you how to write a great subject line. I have a method, as you can imagine, so that’s what I’m going to tell you. So, I guess just to extend the theme – if you could turn on a timer and notice how much time you spend writing email, you would stop wondering whether it’s worth doing it really well. It takes up much of your work day. When I’m offering a workshop and I ask participants, “How much time do you spend writing and reading email?” Sometimes they snort and go, “The whole day.” So, if it’s a task that’s taking up a lot of your work time, then you need to up your game.

Pete Mockaitis
Alright. I’m sold.

Leslie O’Flahavan
Good, great.

[Insert sponsor here]

Pete Mockaitis
And so you said your quote was a method, or that’s just the quote right there?

Leslie O’Flahavan
Oh no, I’m going to give you a method right now. Here we go – so if you want to write a great subject line, here’s a method, here’s a way to try. Write your email first; you’re going to write your subject line last. So you write your email first, and when you finish writing your email you ask yourself a question, “What is this email? What have I written here?” And you’ll come up with a noun as the answer.

So if you’ve written to ask someone for something, then your email is a request. If you wrote that email that I laid out before, you’re telling your boss that, “We should pay this summer intern; we should not try to recruit an unpaid intern this summer”, then your email is a suggestion or a recommendation. If you need to find some equipment that should be in the warehouse but you can’t find it, you might ask someone a question; the email is a question – “Where is that equipment? I can’t find it in the warehouse.”

So whatever is the correct word to describe the email you’ve written – use it as the first word in your subject line. Because what will happen is, your choice of word right there will help your reader know whether she has to do something, even before she opens the email. So if you write a subject line that is, “Request for budget figures for 2019”, then the recipient knows she needs to send you something. You started with the word “Request”; that cues the person who receives your email, “I need to fulfill this request.”

Some first words won’t require the recipient to do something. For example if you use the word “Announcement”. So you could say, “Announcement about visiting scholar in our university department.” The recipient may not have to do anything, and the word “Announcement” tells her that, “I can read this email later this afternoon because I don’t have to do anything in response to it.” So if you choose that word correctly, it does all the work it needs to do to get the recipient to predict how much work your email will be. Does she need to do something? Does she need to read the email now or can she read it later?

Pete Mockaitis
Okay, thank you. And how about a favorite study?

Leslie O’Flahavan
One of the favorite studies… I feel like this study has been done over and over and over again, but there is a 2016 version of the study, and I’ll just highlight the findings. It was a 2016 study by two psychology professors at Chatham University in Pittsburgh, and it was about people’s inability to interpret emotion in email very well at all. And this study has been done in one form or another for about 15 years to my knowledge, maybe even 20 years.

In the study I’m discussing right now, they had study subjects compose an email, identify the emotions in the email, and then they asked the study subjects, “How well do you think a friend would be able to interpret the emotion in this email, and how well do you think a stranger would be able to interpret the email in this email?” And the study found that people were quite confident friends could interpret the emotion in the email, a little less that strangers could. And the outcome was, neither friends nor strangers interpreted the emotion well at all.

So it’s all kinds of scary, because the sender – the person who wrote the email – thought, “Hey, my friends understand me. They’ll get my feeling or my joke or my worry.” And that didn’t happen. What the sender predicted didn’t happen and the recipients didn’t get the emotions correct either. So, that’s just to reaffirm a study like this has been done over and over and over again, that email’s really poor at conveying emotion, that the writers often exaggerate how accurately their emotions will come through. They predict that they’ll come through accurately when those emotions won’t. All that to say, be very careful that your emotions in email are uncomplicated and that you do the work to build emotional connections outside of email.

Pete Mockaitis
Okay, thank you. And how about a favorite book?

Leslie O’Flahavan
I really love the book Letting Go of the Words, but it’s more about digital writing and not about email specifically. So, that’s a heartfelt and somewhat random recommendation. The book is called Letting Go of the Words, and it’s by Ginny Redish.

Pete Mockaitis
Okay. And how about a favorite tool, something that you use often?

Leslie O’Flahavan
It’s a humble little tool called “Spellcheck”.
Pete Mockaitis
Oh, that’s good. And a favorite habit or a personal practice?

Leslie O’Flahavan
Writing the subject line last is one of my favorite habits or personal practice. And also, letting an email rest. Soldiering on, getting a draft and then putting it in the “Drafts” section and letting it rest for a little while before I send it. Lots of times I clear up my writing challenges by moving around, so my dog is always really tired when I have a lot of difficult writing challenges. If I take a walk, I’ll come back refreshed, and so pausing between composing the email and sending it will really help me do a better job.

Pete Mockaitis
Alright. And do you have a favorite nugget, a piece that you share that tends to really resonate with folks?

Leslie O’Flahavan
Yes. I think that helping people figure out what their Bottom Line Up Front statement is, and putting it at the beginning of their email. Put your main point out there. It requires confidence, but confident writing gets great results.

Pete Mockaitis
Okay, thank you. And if folks want to learn more, get in touch, where would you point them?

Leslie O’Flahavan
Oh, you can find me online. You can join me over on Twitter; I’m LeslieO. I would really like if would come to my website – that’s ewriteonline.com. We are a 21-year-old company so this idea that helping people learn to write better email is going out of style, I don’t think so. It’s kind of like selling groceries – the need does not go away. So, please come see us online at ewriteonline.com or on Twitter.

Pete Mockaitis
Perfect. And do you have a final challenge or a call to action for those seeking to be more awesome at their jobs?

Leslie O’Flahavan
Yes, I do have a final call to action for those seeking to be better at writing email, okay? This is my last call to action: If you want to be a better email writer, you’re avid about this, then I suggest you make your own little Smithsonian Museum of emails other people have written that you really admire.

One of the most practical things we can do as people to improve our writing is to read more critically. Try to figure out, “How did he do that? That was a great email. How did he do it?” Or you could say, “She wrote a great email about a difficult subject no one wanted to hear about. How did she do it?” So, get a folder and when you come across a well-written email that you think, “I wish I had written that one” – save it, make a collection of other people’s Greatest Hits, so you’ll have it to return to and you can model your own writing on theirs.

Pete Mockaitis
Alright, perfect. Leslie, this has been so much fun. I think that we have synergized our dorks, the inner dork and good things emerged. So, thanks so much for taking this time. I wish you lots of luck in your training, and many good emails coming your way!

Leslie O’Flahavan
Thank you so much, Pete. And I know that when I’m giving my husband a big hug on December 3^rd and saying “Happy birthday” to him, I’ll also be saying, “And happy wedding anniversary to Pete and the missus!”

Pete Mockaitis
Aw shucks, thank you! Much appreciated.

Leslie O’Flahavan
Okay, thanks very much.