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Composing better emails (iridakos.com)
263 points by laz_arus on Aug 1, 2019 | hide | past | favorite | 157 comments

If you want to compose better emails, forget formatting.

- practice making emails short. Write, then rewrite to 50% of original length, then try to make it even shorter.

- make the request a separate paragraph (request = what you want the other person to do)

- if your email is an attempt to persuade someone, don't bother. Go talk to them. Email will cause you problems in your career if you keep that up. It's unsuitable as a means of discussion (same as Slack and any other written medium). The only reason to do that is if you can't get the other party on the phone/in person (which is almost never the case).

>if your email is an attempt to persuade someone, don't bother. Go talk to them.

This really depends on the person being persuaded and the type of topic.

For me (and I know many that agree), it's better to put a complex topic into an email than to walk up to people. Organize your thoughts, use bullet points, prioritize the most important things, add web links or other evidence to support your ideas.

The problem is that when you just walk up to my desk or call me on the phone to talk about something complex, you're now forcing me to become your secretary and transcribe your notes. I'm now "writing out your email" that I would prefer you write yourself. That's not being respectful of my time. I can read at ~250 wpm; you can only talk at ~100 wpm.

Yes, if it's something lightweight like you're trying to convince me to go to the Chinese restaurant instead of Italian for lunch, go ahead and talk to me instead of write up an email. Otherwise, please consider if the recipient of your complex topic wants to be your "secretary".

I would be very curious of a survey that asked if people preferred to be convinced by coworkers talking to them instead of writing emails/reports with organized and coherent data. Would it be a minority or majority of respondents?

I don't mean for this to be blunt, but since we're talking about work, if I want to persuade you of something, it's your job to listen to me, because my persuasion will be aimed at accomplishing company goals! So we are both on the clock here, not just you.

I can also assure you I speak faster than I type, and so it's not just your end that counts.

I'm also pretty sure I can say much fewer words with proper tone of voice to convey as much as 5x long email correctly, and a single word of your response and a look at your face as I speak will tell me more of what I should understand of your reaction than even the most elaborate written response...

Persuasion and discussion isn't about me laying out my point clearly in a tidy format though, right? It's about mind-sharing, interaction, sensitivity, etc.

Maybe we come from very different types of organizations? I have never, ever (!) in my 15+ year career been in a position where too many unprepared people forced me in any way to listen to their stupid / ill-prepared ideas....

[Edit] I'm also confused, how does someone coming up to talk to you forces you to write anything down?? (seriously I don't get that part :) )

> I'm also confused, how does someone coming up to talk to you forces you to write anything down?? (seriously I don't get that part :) )

Because the most important thing in corporate environment is paper trail. If someone comes to you in person and convinces you to do something you still need an email exchange with summary of what you've agreed on, otherwise someday someone will blame you for a bad decision, and you won't have anything material to defend yourself with.

> if I want to persuade you of something, it's your job to listen to me

> Maybe we come from very different types of organizations? I have never, ever (!) in my 15+ year career been in a position where too many unprepared people forced me in any way to listen to their stupid / ill-prepared ideas....

You truly work in some parallel universe to my own where the laws of office interaction are very different from those I've observed. Are you hiring?

>if I want to persuade you of something, it's your job to listen to me

If you're trying to persuade someone of something, you're the salesman in that situation. Keep that in mind.

>I can also assure you I speak faster than I type, and so it's not just your end that counts.

That wasn't the point; jasode was asserting that many people read other peoples' writing faster than others speak, not that other people can type faster than they can speak.

I get it. But we have to weigh both sides of the cost, and if you want me to type something up, it's not just that you gain by it because you read fast - I lose something because I type slow! And org pays for both our times.

> I'm also confused, how does someone coming up to talk to you forces you to write anything down?? (seriously I don't get that part :) )

Agree with the rest of your post, but this was the main takeaway for me. If you compulsively take notes one every single face to face interaction, that's not my problem.

Well they did qualify with that it was a complex topic. And am not sure he hinted that it was compulsive.

I tend to work in a banking infrastructure environment and it's common practice to take notes,

The number of conversations I have during the day often has me saying, I'm not going to remember everything you've said, could you put that in a email so I can get back to you properly.

It does depend on the environment,

This is one of the benefits of the Amazon writing practice; write up a one-pager on a topic and have a meeting where the first 10-15 minutes are reading the document. Then have a discussion. It's a good way to get to a consensus and it's respectful of everyone's time.

Always do both.

If it matters, do both.

The email is for reference, the walk and talk is for communication, awareness and motivation.

> I can read at ~250 wpm; you can only talk at ~100 wpm.

I agree with your point that reading is better than listening for complex topics, but I don't agree this is the reason why, at least not for me.

I find that when someone is trying to orally explain something complex to me, I have to repeatedly tell them to repeat what they've said. They'll say a complex point, I'll think about it for a few seconds for the implications, and in that time they'll have said more things for which I was not listening because I was thinking of their previous point. I'll wait for a few seconds to see what keywords he'll say to see if I can fill in the lost seconds, and then just tell him to flat-out repeat the last X seconds if I can't figure out what he's talking about now. Telling him to repeat himself every few seconds is annoying to both of us, so I'll mostly just continue with what bits of information I can absorb at the speed he's speaking, and then we'll argue and find out the arguing wouldn't have been as necessary if I hadn't missed some points he said. Then we'll, again, talk about his speaking speed, but realize speaking without consideration of the listener is so core to him that it's hopeless to expect change.

It's mostly an issue with a coworker that doesn't think a bit before talking, as in he's not putting any effort into composing the information as he's providing it, and will just bombard me with mixes of relevant and not relevant information like a machine gun. It's exhausting to be super focused to spot when he's subtly gone off in a tangent and then argue with him about how that information is irrelevant to his previous point so he'll stop and get back on track to the issue.

Text, on the other hand, is usually composed, so the information is easier to digest. I can skim around based on keywords to find the most important information, and I can quickly go back and re-read to make sure I've understood the details of what I just read. I can also absorb this information at my own pace. I don't need to depend on the speaker matching his speaking to my listening.

I can also take my time in composing my reply and tune it so that it solves the issue with as little arguing and time wasted as possible.

Speaking as a guy with a reasonably successful 30 year career: This is mostly not great advice.

- Formatting is useful, and should be used as needed, especially headings and, as indicated, color. Don't become a plaintext zealot. It's not a good hill to die on.

- Emails, like all communication, should be as short as possible -- but no shorter. Brevity itself is not a useful thing.

- The 2nd bullet is, about the request as a distinct paragraph, is good. A proper email that requests action should make that requested action VERY clear, along with expectations and ideally a timeline.

- Contrary to this assertion, email is actually an EXCELLENT forum for discussion in the right context. This is because email is easy to archive, and leaves a trail of the discussion. It's not the ONLY venue, but it's very useful, and in my career has been commonly used as such.

Thanks for the advice! I generally like to keep emails as plain as possible (I do not enjoy the collection of signature images/company logos that accumulate at the bottom of long email chains), but I do try to format important points with bold/color when appropriate.

I have gotten into trouble being too concise in emails! Some people are quite sensitive to requests when they are too short, sometimes it helps to soften the request with a compliment or explaining the extenuating circumstances

ZOMG everyone hates the sig pile. Like, if your signature and disclaimer boilerplate is longer than most of your emails, your company is DOING IT WRONG.

I find restating context, even briefly, is nearly always worthwhile. You never want to make folks scroll down to see the rest of the chain if you can avoid it.

Any written medium is a bad forum for discussion because it completely lacks the wide emotional bandwidth. If the topic is in any way subtle, risky, controversial, etc. you will get more conflict, misunderstanding, etc. in writing than in person, and fallout will be much harder to get away from. That has been the experience of me and many managers I worked with in IT over the years. I would be shocked if you could get anywhere near the results of in-person conversations with written comms. That should only be possible if you are incredibly aligned with everyone in your org (how likely is that?) or you aren't really discussing anything openly (feigned discussions).

All I can tell you is what I've seen as an internal resource, internal manager, consultant, and external vendor over 30 years.

It can and does work. It's not a replacement for meetings (there's no one-size-fits-all in communication), but it is super useful and super effective if used correctly. I'm sorry your job has convinced you otherwise.

What's the median age of people you work with in that mode? (my guess above 35)

It'd be hard to guess, but because we have a lot of younger workers on the front-end of our customers today, I'd guess early 30s.

Nice! I'll think about what you've written. Thank you.

> if your email is an attempt to persuade someone, don't bother.

I think this is completely accurate for most companies, and so sad at the same time.

At a not so extreme point, this means people will pester anyone in a position to take decisions in any possible way. They'll stalk to steal minutes here and there for subjects that can be super complicated and context sensitive, but not important enough to have people stop everything they're doing. They'll book meetings on lunch times, over other meetings. They'll derail meetings because couldn't get a separate meeting. They'll get comments and stark looks because they're obnoxious but it's also the only way to get any decisions from their perspective, and at the end of the day they'll be vindicated as their projects move forward while others stay in the mud.

It feels like hell on both sides of the stalking, I guess it's the price to pay when email or chat, or asynchronous communication is seen as a low tier channel.

Yes, it's bad. In my experience it's because relatively low percentage of people in a typical org have enough trust to one another that they won't misinterpret the wrong way.

Fwiw, I agree with you about speaking in person. I will say though, that I've started to encounter younger people now who will actually come right out and say "I don't do well with face to face conversations and I'd prefer to discuss this on Slack or in a Google Doc" and they somehow get management support for that.

Maybe it's just my crazy company, but there seems to be some kind of thing going on where having any amount of social skills is no longer mandatory. And I'm not talking about awkward people who may be hard to talk to, I'm talking about people where you wouldn't realize anything is wrong and then they go complain to HR that they feel "put under too much pressure" by certain people in face to face conversations (it's not just me that get often reported for this, it's like half the engineers). It's not like they really "punish" anyone or anything for these ridiculous reports, but they also don't do anything to solve the issue of people refusing to talk face to face.

I am not young, and I do better with asynchronous communication. I don't mind chatting on the phone when it makes sense to, but I generally prefer email; it gives me time to think through what I want to say and make sure it's communicated correctly. On the phone, I wind up going silent for a minute to think things through, and other people get uncomfortable because of the silence.

Worth noting, it's not about social skills. It's about having the time to fully think through a complex issue and the information related to it. That just isn't possible during a synchronous conversation. You wind up having meetings where the things that get decided aren't the right things because people didn't have time to actually think through all the factors involved.

Sometimes it takes longer than a few minutes to think about something. I often write out my messages and not send them. Sleep on it, come back and delete to write something better.

I've found myself in many situations where sleeping on an issue provides a much better, thorough and more clever solution than just blasting off an email. If I were to provide responses face to face, there's a good chance I'd be giving bad advice that may cost companies a lot of money.

If you are on a team, and you know you need time & space to think things through, they should know it too (from you). It's your job to tell them, no? Then they either respect that and give you time when you need it, or don't. If they do, no issue. If they don't, they are going to go around you anyway whether you like it or not... just how work works.

> Fwiw, I agree with you about speaking in person. I will say though, that I've started to encounter younger people now who will actually come right out and say "I don't do well with face to face conversations and I'd prefer to discuss this on Slack or in a Google Doc" and they somehow get management support for that.

I can't shake the feeling that the underlying reason (perhaps unconscious) GP recommends using face-to-face conversations for persuading is that these conversations are more successful at their goal than the email equivalent. This is a bad thing, in my opinion. Worse for me (who's been persuaded) and worse for the company.

Compare with advertising. The conversion rate of door to door sales is far better than a classified ad - and the reason is that salespeople are trained to be aggressive, pushy, emotionally manipulative, and force hasty decisions to get what they want. They are able to use a whole raft of techniques to get you to buy that printed ads cannot.

Similarly, rejecting decision making during interpersonal interactions has nothing to do with one's social skills. It's about recognizing one's own susceptibility to being emotionally manipulated in a conversation and rejecting that way of making decisions. Good for me, good for the company.

It's not surprising to me that the "old guard" who's learned to use these techniques in the business world for decades is a bit put off by people rejecting them outright. Then again, I'm sure there are many people who have been in business for decades who are glad to be able to let their guards down a bit with the shift to email. It's not just the young who have this preference, though because most didn't acquire these skills, they are the majority.

  face-to-face conversations [...]
  aggressive, pushy, emotionally
  manipulative, and force hasty
Not every conversation is like that - I don't ask my children to e-mail a report on what their day at school was like :)

No, no. The reason I suggest face-to-face is because only face to face is good at conveying emotion. Everything else falls short in that respect, and because work has a lot of conflict involved, non f2f comms increase unnecessary conflict, slowing everything down, creating (!) personnel problems, etc. People arguing on Slack and email are an HR and management nightmare, they really are. Once you get someone to actually talk in person to them, and then get the parties to talk about the issue in person, things get magically resolved.

I sure hope it's just your company (any, it's not the case at mine). As someone who has difficulty communicating with people, I do anything important face-to-face if at all possible. I have enough trouble reading people as it is. I need all of the extra social cues I can get.

I have to disagree here -- emails are extremely useful for two reasons:

1. It leaves a paper trail (good for accountability),

2. In the case of forgetting a detail or ambiguity, you can look back into the email.

I myself struggle with parsing and retaining spoken language, so I make sure to send email confirmations for specific tasks.

This. Also, bold is shouting, in some circles.

My 'go to' example, when explaining the power of brevity to others, is Hemingway's reputed resignation to his publisher. Vulgar, but a study in brevity: "Upshove Job Asswards".

My second example is also Hemingway, this time from a wager to write a story in 6 words. Hemingway won the wager: "For sale: baby shoes, never worn." https://en.wikipedia.org/wiki/For_sale:_baby_shoes,_never_wo...

I've never heard about bold being shouting. Where is that? IME, all-caps is shouting and bold is merely a type of delineation.

Bold is the single-color equivalent of highlighting. The eye will be drawn to and read boldface words before starting to read the main text, which is why italics are recommended for simple emphasis— from a distance they don’t draw as much attention, but still signal increased importance to the reader.

That's the way I've always understood it too. Italics for light delineation, and bold for important delineation.

I've just never heard of bold as yelling, and am interested to know which cultures consider that to be so.

I agree with all of this, except I've observed that written media can be extremely effective as a means of discussion. In meetings at our company, most of the material discussion takes place in writing before the in-person meeting even starts. The first ~10 minutes of a meeting are spent reading people's comments in silence until everyone is caught up.

It's an unusual approach, but results in faster and higher quality decisions than any other method we've tried.

Interesting. May I ask -- what are the written comments responding to? A question? A problem statement? Is it a full forum-style thread/discussion (with message-response-response...response) or is it a 1-shot style comment from anyone who had something to say before a meeting?

If you want to compose even better emails, learn how to be good with formatting. The linked article makes a fine case of how to.

Just like paragraphs (which are just another form of formatting) using indentations, list items, font weights and capitalization correctly will help you structure any text and get your point across more easily.

It's important to keep in mind that email is quite literally the only domain, where this is even a topic of discussion, solely due to legacy reasons. I do like not having font color and h2 tags abused, but the key to that is email literacy, not taking away formatting options, that are helpful in making the medium work better for humans.

Back when there were no apps like Slack or Microsoft Teams etc Email was probably the only platform for everyday conversations within an organization. But now you hardly need email for day to day trivial conversations within a group. Of course you need Email for a formal organization-wide communication and for all external communications for which you need to put some effort in composition and formatting.

I think your comment depends entirely upon your default style of writing. For me its usually the opposite - I need to pad out my emails and clarify what I mean when I say certain things.

If I am working on a problem I have lots of concept in my head, and its my initial instinct to just write what I am thinking. On reading through the email a second time, I realize that I need to clarify what I mean by certain words / phrases as the reader hasn't been working on the same thing as me for the last few hours / days so their context will be very different from mine.

> The only reason to do that is if you can't get the other party on the phone/in person (which is almost never the case).

Well, for me it's mostly to keep people accountable. If you have written down in an email that the deadline is for day X, there is no way someone could say "well, you didn't tell me"

Reminds me of that quote:

’I’m sorry this letter is so long, I didn’t have time to make it shorter.’

I see you've had a lot of comments disagreeing with your assertion that email is a bad way to have a discussion. I think I understand your point, and I too feel that my discussions are most effective in-person, followed by video chat, followed by phone, and finally in last place written simply due to the varying absence of body language and voice tone.

That said, I must disagree within the business context simply for the following reasons, all of which effect me daily in my career:

1. The Internet is global, the world is global, not everyone is a native English speaker and it is necessary to be very clear, and give sufficient time for understanding. Written communication facilitates this by being asynchronous and providing a pathway for transliteration. In my current role I interface with people across more than 60 countries to get large, complex, technology and engineering tasks completed. Email (and to a lesser degree Slack) is essential to this.

2. I work remotely, as do many of my peers, this makes a face to face conversation basically impossible. As a rule, an office culture of having face to face conversations as a preference subtlety devalues the contributions of remote workers and creates a separate political hierarchy within the organization based on higher rapport from face-to-face conversations and the availability of the "hallway track". By building a culture of written, asynchronous communication, we ensure that /all/ employees are on equal footing across the company both politically and materially.

3. My technical projects are of sufficiently high complexity and need a very high level of shared understanding, and that complexity is difficult to communicate with accuracy and precision in spoken word, as it often needs illustrative images accompanying an explanation. Rich text and images together are far more effective at communicating this complexity than speaking to someone. Better yet, is often a demo done via screen sharing or screen sharing for pair programming work.

4. Everyone is busy and has their own personal biases and priorities, as applied to the workplace. To ensure everyone is moving in generally the same direction and aligned to the company goals and team goals, it's important to have accountability. Providing information in a written form which is traceable (email) helps drive accountability and provides everybody involved a point of reference to help them stay on task.

5. An email inbox can act as a rough to-do list / priority queue, and face-to-face conversations act as interrupts on that queue. While you might be "more effective" at getting the things you care about done by talking to people face-to-face, you're doing so at the expense of other things they could be spending their time on which may be higher in the priority queue for the organization. What is most important to you personally within work context may not be the most important thing to the company. Forcing a face to face conversation is taking advantage of the rules of etiquette to manipulate the priority queue.

Just a few things to take into account. I think every work environment is different, and it is also easy for us to be biased into a belief that the most effective thing for ourselves is the most effective thing for the organization. This isn't necessarily the case. Often an organization gains net efficiency by using less efficient processes at an individual level which scale more effectively and have inherent checks and balances for accountability, and email is one such case. There is a reason why email is so prolific, basically irreplaceable, and hasn't really been dethroned since it become commonplace.

Thank you. Something to think about.

This is the best advice.

I would also add "promote the most important message to the first sentence/paragraph". Rewriting the first example:

  Hello all,
  Please check and revise the priority of Redmine issue (#455) that I have created.
  I noticed that there are many logs for blabla the last few days and I don't think that it is normal. 
  I believe the problem is the updated version of gem blabla.
  Feel free to change its priority in case blabla.

The first sentence in most cases should be what you require the receipient to do. The rest of the email can then be why you want them to do it. This has the beneficial effect that the receipient can immediately tell from the first line how important the email is, how time sensitive it is, and how much time and other resources they have to commit to resolve/reply to the email. Examples:

* Check issue (from the above example)

* Giving you a routine update (no action required from receipient besides reading the email)

* Set a meeting (receipient needs to determine when they are free to discuss the why of the email)

* Give me permission to do X

Generally known as BLUF in my circles - Bottom Line Up Front.

My approach would be to have subject "Check and revise the priority of Redmine issue (#455)". I'd then put an explanation in the body of the email. That puts the task in the inbox, and they can open it if they want to see the details again later.

This has helped me when there are multiple things that have to be done. I now usually send several messages rather than one, with one task per email. In the cases that is not practical, I make it clear in the subject that there are several things to be done, and the body starts with a list of all the tasks.

This is also highly beneficial in cover letters and résumés (keep the most important info at the top).

TL;DR or BLUF line should be mandatory.

Full stop.

Sometimes we use obfuscation for social reasons

- because we don't want to offend some direct recipients

"We see a future using efficient automation techniques to improve shareholder value"


"we are firing the expensive useless third of staff"

- because we don't know the current opinion of people on the list

"We should investigate the options"


"We are all agreed we should use the new design so let's do that"

- we are not sure who the decision maker actually is, or if this is even a problem

All of the above may come off as lack of confidence / inability to write clearly but generally it is awareness of difficult social situations that if not handled well would derail the ultimate outcome - in short just because people are not writing "hard charging go getting emails" does not mean they are ineffective - perhaps they are more effective than the bull in a china shop

Being aware of the power structure/corporate politics going on at your workplace is really important if you want to advance.

Also when you work across cultures you need to adjust your tone/approach. As a German working with French coworkers, it took me a while to figure this out.

> As a German working with French coworkers, it took me a while to figure this out.

What examples come up the most, or had the most impact on you figuring it out?

As an American working with Europeans I've found that there is often a different tone in communication used. It seems to me Europeans are often more direct in their conversation (which in email may sound rude). It took me a while to figure out why Europeans were being rude to me via email (they weren't). After some time a pattern emerged and looking up the issue made it clear that this is just how the cultures differ in communication.

i.e.: You have to put people in "To" and "Cc" by order of importance in the company and respect the hierarchy.

I thought this was crazy and egotistical, and how could anyone even want such a thing... until I googled the topic. From what I'm reading, it's not that rare (https://workplace.stackexchange.com/questions/97395/in-what-...).

In my mind, order serves no purpose, so requiring it is purely egotistical. That being said, overly egotistical people aren't exactly a rarity in the business world. And the minute _one_ person says it matters, other people start thinking it does too (because someone else might see it that way, and it reflects on them).

I had an idea that there is a business in making a "widget" that just applied a alphabetical order to a list of people in To:

I just could not figure out how to write code and distribute it in outlook ... not that I tried hard

Never heard of this here in Germany.

Also "cc" is rarely used where I worked and was mostly then used to inform the people in cc about the issue, they aren't required to do something.

should this have been "e.g." or is this really the main thing needed to respect hierarchy?

That is an interesting one, thanks!

From my personal experience, Germans and French have a completely different approach to project work/management/planning. Some backround: we are a German dev team, but our product management and release planning is located in France.

Germans need a clear plan/path, how to get from A to B, with concrete steps that need to be taken. If no such plan is in place, the uncertainty makes us feel uncomfortable. We also need to know who is responsible for what, who is the point of contact for which problem and who will/can decide what. That should ideally be clarified in project kickoff meetings. Meetings in general must have an agenda, the goal and which questions must be answered must be clear. This also drives who should attend the meeting.

French not so much. They are totally fine with not having a detailed plan. They just start with the work. They feel/think that "things will get sorted out when the time comes" and "someone will do it" or "someone will remember to bring the item to the meeting". To them we Germans are way to much stressed out about the plan and project structure. Meetings will be announced where there is no clear agenda, the goal is just "to align everybody" which often results in an unproductive mess.

For a long time I thought that our product management just did not have their shit together, that it was always chaotic, with change of plans on short notice, not giving a headsup on important topics and information getting lost in the shuffle or not reaching the right person etc. Their communication style is also more indirect, not confronting people/issues in meetings, but rather sit in silence through it and then later complain/being irritated about what happened in the meeting.

A year ago I was lucky to pick the brain of an much older Begium high profile project lead (from a completely different company/field) who had worked a lot with French and German teams on many different projects. He said he preferred working with German over French teams and roughly described what I was experiencing. Then it dawned on me, that this is not incompetance, this is just how they operate. I talked with my french manager about that and he was like "yeah totally", he outright said that he loves it when the plan is fuzzy and the scope is unclear.

From there on I saw many things through a much more understanding lens and respected their way of doing things. (For example, where we might overthink and over analyse stuff, they just start and get shit done. Or where we stress out about defining in detail processes and responsibilies, they also "just do it".) And actions (or inactions) that sometimes lead to (for us unexplainable) friction became clearer to me. I also realized, that you cannot change the people (and their working style). You have to adapt to it and compensate for the things that bother you (ask for an agenda, ask who will explicitly do what or better just do it yourself, bring the items yourself, etc).

For the “structure long messages” bit, i was taught to use the SCRAP mnemonic:

Situation: x has broken

Complication: dev is on lunch

Resolution: wait for dev to return from lunch and request investigation and thoughts on fix


@dev finish lunch;

@teamlead inform @dev when returned from lunch;

@dev investigate problem and report to @teamlead;

@teamlead update @me on progress;

@me inform clients on issue

@me setup meeting to discuss potential fixes with @teamlead & @dev.

Politeness: have a good lunch everyone

I've used an almost identical method, but never knew this had a name, or such a neat mnemonic!

Those are some nice tips, but I have to question the use of bold font, it seems to come off as too aggressive.

To me, it feels like the sender wants to yell particular words at me because they feel like I'm not capabale of digesting entire sentences.

I agree and I've been using italic instead of bold font for this reason. It's like you're whispering something which makes people listen more intently and hopefully read more intently.

It's very strange to me that some people actually don't like bold text to emphasize relevant parts.

It's the easiest way to aid speed reading/allowing mental prose-to-bullet point conversion.

For me it's a sign of respect for time of the reader who is likely overwhelmed with information and wants to focus on the most important parts.

I've written some technical documents this way. In one company I got explicit email that this helped a lot and was great idea. Implementation that followed went smoothly.

In other company it has been seen as silly, all emphasis was removed, bullet points expanded to prose, useless brochure like logos/typography added - of course I'm biased but this document stands in my head as the shittiest/least useful/confusing/verbose documents I had to deal with.

I think to really appreciate this approach you'd have to test it yourself on 50 page document and discover how fast you can digest 80% of information included.

Likely practicing speed reading will help to appreciate it more.

It's a bit like medium highlights - but it's designed by the author, it can be really, really useful, but it's niche and very rare to see unfortunately.

Although I feel the same surprise as you, (I didn’t realise some people would interpret bold as yelling/condescension) ... I’m going to change the way I use it.

I can’t control the reader, only my writing, so I’ll switch to italics or even monospace (I’ll test both)

I have never read italics as whispering. I usually read it as emphasis or stress. I read ALL CAPS as shouting. I read bold as important. I only see bold as aggressive if emotionally charged language is bolded (ie: marked as important by the writer).

I find it interesting that others may still perceive these differently than either of us.

Actually the first example is very telling. It seems the writer is using bold face to try to emphasize part of the sentence that doesn't matter that much. The first sentence I'd the important, the second with the "why" (the blah blah) doesn't matter

Totally agree. Sometimes I'll use a monospace font for highlighting things in a generic way without it looking condescending.

Agreed. I generally delete everything but the bold sentences.

Anyone who has read any of my posts here knows that I suffer from an inability to speak concisely. I feel I have a talent for being able to get my message across clearly and this has helped me a lot at work. However, I have trouble keeping the message size small enough so that most people will read to the end.

Does anyone have any advice for improving on this front?

It is likely that you provide more context than necessary. For example, you could've asked:

"My emails tend to be too long. Does anyone have tips on writing concise emails?"

Obviously your post was not an email, so the additional, narrative context you provided is welcome. In emails you should aim to provide just the key info, and to elaborate on any context in other forms of communication/documentation. I typically try to aim for just 2 lines of content. One is a statement of fact or a problem, the other is a question or a 'call to action'. I break this rule often, but I always pause to think if there is really a good reason to stray from that rule or if I'm just ranting/chatting.

Often if people want context they'll come find you or call you.

Rephrase, simplify, eliminate. For example, your comment could be written as:

> Frequent readers here know I write verbosely. I communicate clearly, but few people finish reading my messages. Any advice?

William Zinsser's book, On Writing Well, covers this topic. I recommend it.

Yes, write short.

This is the title of one of the chapters in “Writing without bullshit”, hilariously followed by the first paragraph: “Use fewer words”.

Other tips from the book:

* Edit everything

* Aim for a word count

* Say what you really mean

* Start boldly

* Organize relentlessly

* Prune sections and arguments

* Use bullets or tables

* Use graphics

* Trim connective tissue

* Delete weasel-words and qualifiers

William Strunk would shout to his class:

"Omit needless words! Omit needless words! Omit needless words!"



Umberto Eco would have added ;-):

13. Don't be repetitious; don't repeat the same thing twice; repeating is superfluous (redundancy means the useless explanation of something the reader has already understood).


* Practice writing more concise emails. Especially if it's an email you already sent out. Ask yourself if the email had the intended effect, and what changes you could have made to better reach/improve that effect.

* Look at the emails you receive that you feel do a good job of being concise. What do they have in common? What do you do differently from those emails? Start applying those differences when you write emails.

* Look at the emails you receive that you feel don't do a good job of being concise, or are confusing otherwise (perhaps they're too concise). Open the email in an editor and make changes until you eliminate the problem areas. Can you make similar changes in your own emails?

As a more concrete example, I originally had this text in the above paragraph:

> Open the email in an editor and make the changes you would want to see until you see the email you wished you received

I then revised it to:

> Open the email in an editor and make changes until you eliminate the problem areas.

In this and other cases, messages can be improved with better handling of the sentence's subject(s), tense, etc.

Judicious editing.

I think the Blaise Pascal quote about not having the time is relevant; making things concise takes more effort, particularly if you are not already in the habit of doing so already. Start with your communication, remove redundant or unnecessary words, then think about ways to compact things down even further by removing or rephrasing sentences.

Going through "Elements of Style" by Strunk & White wouldn't hurt too.

> remove redundant or unnecessary words

Made me chuckle.

Hah! Both words have (slightly) different meanings, but yeah, I ironically didn't follow my own advice :-)

I think your message asking for such advice is itself of a suitable length where the problem is clearly stated without deviation or distraction.

Taking your message on it's own, you have the ability to keep the message size small.

Keep to the point, avoid distraction, stay focused, replace three words with two where two will suffice, replace two words with one where fitting. Omit needless words, make each word count.

Additionally to the tips from the story, this guide might further help you to focus the content of your mails and the delivery of the important message. It certainly help me.


My approach:

When reading what you've written, find the core of what you're really trying to say. Find the sentence or couple of sentences that conveys this core. Then see if the other sentences are really needed, removing those that aren't, tweaking the core as you go along.

Repeat until you feel it can no longer be distilled further.

Put all the important points right at the start: bottom line up front “bluf”. Explicitly mark the point where your message becomes background detail, so people can stop reading there.

Perhaps use an email client that has a Twitter-like limit on message length :)

I like and follow most of this, but the most important topic is missing: use meaningful subjects! I don't want any "Re: Re: Re: Fw: Re: issue..." emails in my inbox. Especially if I later want to find some specific email.

This. As an anti-spam measure (that worked flawlessly so far), instead of putting an email address on my website, I have my website send an email to people with the "From" address set to my address. The subject is something like "To reach me, just reply to this email!"

A bunch of people used it, but not a single one managed to change the subject line to describe what their email is actually about. Not one.

Well, maybe you should add: ... and change the subject :)

It's no biggie and sure I can change it to "change this", it's just odd to me that nobody sets the subject line.

Especially when addressing multiple recipients, I tend to write emails like:

> Hello,

> Short version: all-hands meeting to discuss painting of the bike shed, Thu 1 Aug @ 14:30 in the board room. There will be cookies.

> Long version:

> <more details>

I also tend to first jot down a draft of the "long version", then edit it for clarity and brevity, then write the "short version" last.

Edit: I find HN formatting weird sometimes.

Like TL;DRs on Reddit! Interesting, I think I'll incorporate this concept for my long emails, thanks for sharing.

Per the request of one of my early bosses, I include TL;DRs on my emails when they get long. It can save people a fair amount of time.

I highlight emergency/mistakes an bad things in general with red background. Resolved situations or positive approach with green background. In both cases white and bold font.

After a while, the same color pattern is emerging from customer communication.

I had been a “true believer” in plain text email until I had a support vendor document a problem using just this technique, including output from the system in question in fixed-width font.

While I cringe at the majority of HTML email, this use case I find enormously valuable.

I like his recommendation to attach cat pictures to the Post Scriptum of every message.

Personally I was hoping the cat-picture-meme would be a passing thing. I am allergic to the little critters and am not particularly fond of them. They carry parasites and bacteria which can be permanently harmful for us.

So, although I respect people wanting to have their own pets and take care of them, I (and many others) think it is tasteless to project this affinity to others in a professional setting.

"Lazarus Lazaridis' personal blog with posts mostly related to programming and opensource. And cats." I agree completely that "cutesy" things don't belong in professional contexts (I like to make sensible exceptions occasionally to reassure everyone that I am, in fact, human), but these are his critters, so he is entitled to subject his readers to them (just like someone who posts pictures of their happy-smiley family). Also, you should be more concerned about humans, who carry parasites and bacteria (and viruses!) which are vastly more dangerous to you. :)

Although I vehemently disagree with you about cats, I feel pretty much the same way about the stupid dog gifs that my boss insists on putting at the top of our monthly report drafts, so I can see where you're coming from.

The thing is, it's not an actual cat/dog. It's not going to get dander or slobber or parasites on you. I just scroll past and forget about it.

Neat! I have a dream - just like we have issue templates, have organization wide email templates for internal communications. If every email sent in an organization, adhere to 3 to four email templates - that would take away so much of the cognitive load of parsing each snowflake and extracting the meat out of them. As soon as you see a label in the first words of subject you know what you are dealing with - like "bug", "defect", "enhancement" - put "delay", "escalate" etc. Instead of a free form text box with no word limits, there will be more fields that enhance decision making - voting buttons, highlights like you see on medium.

The word limit will stop the mind dump and make you be precise with the focus on reaching a goal.

Some more unpopular ideas:

* A discussion would have follow up limits. Time or number. No month long threads, or 100 replies in half hours. Beyond a limit, it will automatically schedule a meeting for in person discussion to conclude on decisions

* email quotas - you can only send n emails within m hours to p persons

I am missing one thing from the article: Your subject should be a clear, concise summary of your mail! People will be looking at the subject of your message MUCH more often than at the actual body.

Putting a word in boldface is even more offensive than writing it in ALL CAPS. If you are doing it more than once per year, you are doing it wrong.

If it's just regular language in most contexts, I agree.

But for technical communication where you're using names of things that have a controlled vocabulary, it's really helpful to put those words in a bold mono-space font. Otherwise, you end up using quotes too much and that gets tiresome.

Is this a common opinion? I find bold text to be very helpful since it emphasizes the most important part.

> Is this a common opinion?

I said this as a personal opinion; no idea how widespread that is. Boldface strikes me as a lack of respect for the reader. An adult reader is supposed to read the whole text. If there is non-important information, please omit it.

The idea if writing a short sentence at the beginning summarizing the action to take is sound, however. It is even better if it appears in the subject of the message.

> Boldface strikes me as a lack of respect for the reader. An adult reader is supposed to read the whole text.

Yeah, that's bullshit. Open any CS book on your shelf and you'll see different fonts, different sizes, different weights, different background colors, etc. Those books are not written for kids, they're written for adults—for professionals. The goal of a writer is to control the reading process; changing what the text looks like is one way to do that.

We separate the text into paragraphs to delineate different ideas, but also to space out the text and give the reader a chance to breathe. We organize points into bullet points because they're easy to spot, easy to scan, and we don't need to make the text longer by adding flow between each point. We sometimes use frames and a darker background for summaries, auxiliary information, etc. to show that it's not part of the main text. We use large letters to identify different chapters and sections. We use a monospaced font for code examples. We write technical terms in italics when we first introduce them and want to highlight that fact to the reader.

There are a multitude of ways in which we format text so that readers can better follow. Bold is just one extra tool in that arsenal. Don't abuse it, but don't forbid it entirely either.

>An adult reader is supposed to read the whole text.

I wish to work in the utopia that is your office if this is even slightly true in practice.

I tend to emphasize not a lot in emails where a reader that's skimming might skip the not and get the opposite of the impression that I intended.

Pro tip: good subject lines improve the chances your email will be read, acted on, remembered, and found again later. Every marketing person knows this but the importance doesn't seem to leave that domain. Make them 45 characters or less or so.

Bad: "Question" Good: "Any avail. tomorrow Tues. 12/2?"

Combine actual dates AND relative ones. Days of week help.

Bad: "Millie Smith" Good: "Millie Smith asst. dir. new hire"

Bad: "Tuesday" Good: "work from home - Tuesday planned power outage"

Bad: "report" Good: "2Q19 sales dept. new business report"

Bad: "canceled meeting" Good: "Wed. 4/3 sales meeting canceled"

I try to keep most emails short: (Approximately) 3 sentences, broken into 3 paragraphs.

That's most peoples' attention span for email.

I only write longer emails when someone asks me a question; such as when a manager asks me to research and root cause something. Even then, I usually try to follow the 3-line rule, then put a ----, and then the longer email.

BTW: When I get a very loooong email, sent directly to me, I don't read it. I will usually reply with something like, "I don't read long emails" and suggest that the author find time to meet with me directly.

> reply with something like, "I don't read long emails" and suggest that the author find time to meet with me directly.

Everyone you suggested that to thinks you are a dick. They spent half an hour or more writing just so you can absorb the information asynchronously at your convenience rather than having to schedule yet-another meeting and take notes -- and then you want to waste another half-hour of their time because you can't be bothered reading.

It's usually not a case of "absorb the information asynchronously," instead, it's being upfront with ignoring rants.

I don’t fully agree with the bold part. I think a better way is to have a small sentence summary at the top of the email. Like “I’ve started working on the backup issues.”

This is in direct conflict with the "Use plaintext email" post from a while ago but I honestly agree more with this one. Is Markdown in email a thing yet?

I know this isn't the question you were asking, but ostensibly, Markdown in email has always been a thing, since it's intended to degrade gracefully to human-interpretable formatting.

Markdown is actually a markup language which was inspired and built based on traditional email formatting.

Interesting! I'm newer to software and have never done any communication about bugs or other situations the article references via email-- it's always been in person, in a Slack channel, or through JIRA or Github comment threads.

I guess it's just my company's culture but it's always been assumed that people will not check or respond to email promptly, so project-related information should not be communicated that way.

I'm a big proponent of using specific times and dates instead of—or in addition to—words like "tomorrow" and "next week." It makes your email easier to understand if you are looking at it any in your email archives or if you communicate with people in different time zones.

I work for a general contractor which has projects in all time-zones in the United States (Minus Alaska/Hawaii).

We have many 12 hour day shift and 12 hour night shift projects that are running 24/7.

Using the exact date you are referencing, using military time along with timezone has been invaluable.

For example,

"John Doe,

We are moving the security clearance fingerprinting to be held next Friday, August 9th at 14:30 EST"


"Jane Doe,

Just following up on the RFI we submitted yesterday, July 31st at 13:30 EST. Were you able to review?"

This also helps when having to hold people accountable for not responding fast enough when you include timestamps.

This also makes it easier to catch mistakes. If you had said "next Friday, August 8th", maybe you actually meant next Thursday.

It tends to make you even more angry, though, if you took extra time to emphasize and link messages and you get a unformatted, half sentence reply from someone who clearly did not read the message. I think you should do it anyway, but be prepared for frustration.

While completely true, this viewpoint is a little cynical. The challenge in those instances is to think about how to lead these people positively to do the same?

How can you make emails seem like a gift? That's how I approach it when I write my best ones.

At some point when I need to “structure an email” usually that’s a red flag to me that I should format it as a report in an attached document (which can be more detailed) then make the email a handful of sentences describing the attached report.

I think the "Structure long messages" section could be more succinct. Background, Consequences, etc (unless they're company standards) don't really impart much information. It could be better to instead have practical info as those titles.

e.g., instead of Background, have "Huge increase in log messages". Instead of "Cause of the problem" have "Caused by bug in external library". That way, if people only read the headings, they still get a useful understanding of the issue immediately.

I always hesitate before using emphasis.

I’m afraid it will looks like I think the recipients are stupid or something.

But seeing it’s a good advice will change my view on that (I tend to write long emails)

I disagree. I always highlight in bold text the parts that I want people to focus on more, especially in longish emails, or those where there are numbers involved. I also appreciate it when people take the time to highlight what they would like me to pay attention to. It shows a mutual respect of time.

Absolutely, you nailed it. It's adds a condescending tone. And no, it's awful advice.

Huge missing thing: SUBJECTS. Please use descriptive subjects.

Indeed, it's the MOST important part.

Easiest way to do it - write it dead last.

Write your email in this order: 1. Body of email 2. Formatting: fix the paragraphs, bold/underline, create headers if longer piece 3. Subject line

> Easiest way to do it - write it dead last.

Yep! Agreed.

Still i constantly receive mails that are not descriptive enough. If there are IDs to change requests, deploys etc, why don't you put that ID in the subject so it's easy to get to it later?!

Is this a joke?

What, specifically do you disagree with? Personally I go the plaintext route for email, but if I was writing HTML emails this advice all seems pretty sound to me.

Nope, unfortunately, this seems like a serious, well-intended advice piece :)

This is a pretty great summary of effective email communication. People would do well to internalize it. I'm glad to see it here on HN.

I feel like emphasizing is hiding the fact that your email contains arbitrary things.

I tend to not decorate and encourage people to read the whole thing.

Less is better.

And on the subject of what most not to do....

For pity sake don't send a picture of a log or an error dump..... send the text.


Pretty please.

With tears in my eyes.

Or you know, pick up a phone and call. I think for most people, it is very rare that they write an essay of an email to someone. And if you are an academic or some professional, you should be doing these things anyways. Or is that the point?

Obligatory link to an explanation of the BLUF ("bottom line up front") format: https://hbr.org/2016/11/how-to-write-email-with-military-pre...

I see too many people write long emails, both in total word count and in word count per paragraph. Then they wonder why it takes someone 1-2 weeks to respond.

Unless you're working in an environment that thrives on them, such as academia, a long email creates a significant cognitive burden on someone who is probably trying to context switch as fast as possible. Combine it with a lack of clear action for the reader -- "What are your thoughts?", for example -- and you will find your emails left indefinitely on their "too hard" pile.

TL;DR Use HTML features (and dates).

Yes, it's 2019 and I'm still in favour of plaintext emails. Sorry.

Me too. This is exactly the area where something like Markdown should have flourished.

At worst it looks like plain text with a few _ and * characters sprinkled around, it has beautiful clean HTML output and some terminals support italic and bold fonts; win/win/win.

Pity that boat has long since sailed.

Adding links and plaintext emails are not mutually exclusive. Hackernews comments are a great example where commenters often embed a [1] tag in their comment and at the end of the comment have a section like

[1] https://news.ycombinator.com

None of the HTML features the author uses lack a plaintext equivalent.

I disagree. We've been doing this for decades on mailinglists

# example heading

You can add emphasis with asterisk or _underscores_. Links can be done with [1] tags

And as an alternative, nothing stops you from using Markdown syntax in plaintext emails for adding structure like (nested) bullet lists.

[1] https://news.ycombinator.com

I think you misread the comment you're responding to, and are therefore agreeing.

Actually, I wonder why the author decided to use a monospace font for his examples. I mean, isn't it one of the less disputable facts, that monospace fonts are harder to read?

Maybe it's just a bad example in the article. It seems like a regular conversation between a group of people to get things done in an organization. At least in our organization that type of conversation happens in a quick meeting or some collaboration app link Slack or Microsoft Teams, formal composition of messages is not necessary in those kinds of platforms. Email seems to be an overkill for stuff like this ...

I find the idea that email could be overkill compared to any length of meeting to be hilariously backwards. Maybe it's just the particular dysfunction of my organization, but any meeting between more than two people requires multiple emails to set up.

[ Hello all,

I noticed that there are many logs for blabla the last few days and I don't think that it is normal. I believe the problem is the updated version of gem blabla.

I have opened an issue describing the case in Redmine (#455) in the current version. Feel free to change its priority in case blabla.

Thanks, Lazarus ]

My point is that the above piece of conversation happening over an email is super slow and backwards. Lazarus should just be able to talk to the group directly which a platform like Slack or Teams makes possible.

We clearly exist in radically different worlds. To me, sending that email is talking directly to the group. Nobody at my org uses Skype (our organization's IM service of choice). Email works just fine. If it's actually important and the person or people you're emailing are actually available, email is no slower than IM/chat.

I agree Email is slow is an arguable statement, for email you need to add recipients sometimes CC and BCC carefully plus you need Hi/Hello/Thanks/Signature etc which makes it more formal for daily communication for getting things done. My Second issue with email is, in the above example let's say Bob and Alice have different questions about Lazarus's email and start typing their responses at the same time and send them. Now you have 2 different threads of the email and this can go on and on and in no time you have chains of emails flying around. Let's say John (one of the people copied on that email) is on vacation. He is going to have tough time trying to go through that mess and piece everything together.

This is great advice. Thanks for posting

These examples looks like bug reports that I don't want to read.

The bold/non-bold text, email not balanced and too long paragraphs mixing numbers and letters makes me wanna vomit, not because it's disgusting but more like when you read in a car.

I agree with links though.

I need to spam this in my company

In case you TL;DR, the takeaway:

- Keep it "concise", "ascribed", and "specific". By concise, avoid irrelevant details; by ascribed, write necessary data even though it's obvious but saves time for the reader by not having to look up, i. e., complete date mm-dd-yy instead of yesterday/tomorrow, links for references; by specific, avoid ambiguity, separate lines for each required query.

- Use proper text formatting, i.e, <bold> important texts, wrap links with titles.

- Divide long email into separate paragraphs, each can contain its subject. i.e., the way most SaaS services publishes postmortem about an outage or vulnerability.

Note: I've read many articles on writing good emails, this article focuses on the technical team, which in itself follows its guidelines.

Christ, this is terrible advice. So overzealous and at times I get a childish vibe from the emails written. Please don't do any of this people.

Really? Aside from the emphasis and cat pictures, this all seems like basic advice that's borderline mandatory if you want people to actually read and understand your emails. If you have specific rebuttals to using specific dates, including relevant links, structuring emails well, and making action items clear, I'd really like to hear them.

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