A Case for Email Etiquette

Paco Nathan
Jul 17, 2016 · 12 min read

This, in response to this. See “Backstory” below for more info.

Our notions of #InboxZero or “email overload” were probably not among intended outcomes when Ray Tomlinson hacked CPYNET protocol to blend it with SNDMSG for the first networked email in 1971.

Here are a few recommendations for using email — collected from the Interwebs since when guyliner met slogan tees. These are proven to resonate with some people and thoroughly ruffle others. There are good reasons, mostly involving asymmetric actions — which by the way is a euphemism for nastier deeds, in some circles. See “The Basic Problem” below for more info.

Talk about disruptors… some of those most upset by rules about messaging will be people seeking new lines of work soon anywho. A reality check is perhaps an artifact of their initial stages of grief. See “MSFT Acquires LNKD” below for more info. YMMV.

Suggestions for use

The following patterns and anti-patterns help provide rules for email etiquette. It’s a starting point, in the very least.

It Never Hurts To Ask: Yes. Yes, it does. Especially when you ask for too much, too often, without consideration flowing in the other direction. For example, typical messaging via LinkedIn mail (not just InMail) falls into one of the following:

  • make an intro
  • perform some work
  • help recruit / fill a role
  • get a customer / close a sale
  • help fund somebody’s venture

Each requires action, time, attention, though rarely gets compensated. Many are less than ethical, or at least ill advised. One might simply ignore the garbage in LinkedIn mail… unless that channel has other important messages coming through. When you use messaging of any kind, keep in mind what you’re asking. Keep in mind that attention is inherently scarce.

OTOH, email filters on services such as Gmail are almost trivial to create and simple to access programmatically. While it may violate laws for a commercial service to publish a “naughty list” of bad actors online, there’s nothing stopping one’s trusted, close friends from sharing who they’ve blocked and perhaps a tag or two why. Nothing stopping one from using that info to enhance their own filters and establish business preferences. In other words, refusing to do business with confirmed bad actors.

Gibson’s Bridge Trilogy explored a division of have’s and have-not’s partly based on an “inverted kill file” as a McGuffin. The scenario is becoming increasingly believable. Those who ask too much, too often, may find themselves occluded. We think of “Big Brother” technologies being in the purview of large governments or corporations. The technology exists now for tech-savvy individuals to build walled gardens of commerce cost-effectively. Perhaps already a practice at scale.

Harmonize: People tend to sync their rates of reply. Try experimenting… answer an incoming message within minutes and you’ll likely see a quick response. Let that message “age” for a week before you reply, and the response may be delayed. Generally, correspondents will tend to synchronize close to your rate of response.

So you can slow the rate of email exchanges. Perhaps someone’s communications are helpful, but way too abundant. Answer immediate needs first, especially for people who are civil in their email practices. Let the other messages “ripen” first.

Inline: It was a thing, in the 1980s. Someone sent you a message and, to be considered couth in geek culture, you’d studiously quote each paragraph, answering point by point directly below each quote.

Leave that aging geek practice back in the past. Long email threads lead to utterly unreadable messes.

Instead, here’s a radical alternative… when someone sends you a long email with numerous actions requested, select one key point and reply to just that with a one-liner. Two of my editors have used this approach with most of their email. The effect is sublime. Civility, encouraging focus and priorities. It’s contagious.

CC The World: Email threads sometimes grow long. Stated a bit differently, sometimes threads grow wide by cc:’ing many people, and grow deep by quoting each and every exchange.

Here’s a different tact… don’t reply to everyone and don’t quote the entire message. Ask yourself, who needs the info? And what info in particular? Only reply to 1–2 people with just the salient point quoted. Elision can work wonders.

Similarly when a message already has more than N replies, don’t add to it any further. You must decide the value for N given your organization and your role within it.

I’d love to launch a new kind of email service where everyone in a company gets an email attention budget, reset at the start of each week. Their budget measures how many messages they send, how many people they cc:, how much text is contained in each message, etc. When they exceed budget, they stop participating until the start of the next week. Likewise, when a thread exceeds thresholds for number of replies, cc: lists, etc., it simply ceases to propagate. This could really help for group chat, too.

Gladly Pay You Tuesday: Don’t send messages requesting to send messages, e.g., email asking “Can we talk?” or tweets to ask “Can I email you?” In other words, “I’m sending you a message about sending you a message.” The recursion becomes painful.

If you use a digital medium to reach out to a person, conduct your business while you’re taking up that other person’s attention.

Land-grabs: Almost every organization has some set of people who are toxic. Tyrants in training, raging narcissists, borderline personality disorders, misogynists and racists galore, land-grabbers who seek power at any cost.

Oddly enough, these people often employ email to do their dirty deeds. But email is an Achilles heel for these types. It’s too easy to copy and share evidence privately in a backchannel. Or resurface during cross-examination in court.

Avoid them, op. cit. “CC The World” above. Or help turn those cross-ex opportunities into reality. Your choice.

Let’s invert the scenario. Express thanks for someone else’s time, effort, and attention, whenever you request it.

Rolodex: Keep track of who in your organization behaves with civility w.r.t. email and other messaging, and who doesn’t. Perhaps you can find ways to work more with the former and less with the latter? Perhaps a lot of others in your organization would prefer more of the former and less of the latter too?

The Basic Problem

Here’s the basic problem in two parts: (1) you have a nervous system; and (2) there are 24 hours in each day. For at least about half of those 24 hours, you do something other than process mediated experiences through your nervous system: work, school, mind after peeps large and small, forage for food, sleep, etc. The hours of the day in which you can choose where to focus your attention dwindle down to a precious few.

Physiological limits constrain how much attention you can spend on anything during a given day. There’s an upper bound. Sometimes those limits change drastically due to fatigue, illness, stress, hurricanes, fires, riots, legit concerns about important matters, others’ needs, reality swooping in, etc. Keep in mind that deficit spending, supply-side economics, hedged trades, leveraged buyouts, corporate rhetoric about productivity, and other slight-of-hand tricks from the Era of Financialization do not apply for extending individuals’ attention. Simply put, whenever a technology “feature” or organizational “practice” violates your physiological limits, somebody’s pitching you on the virtues of magical thinking.

One important thing you can do to take an active role in the media battle for your mindshare is to model your attention budget. Start now. Quantify the constraints of your POV first, then extend out to model realistic constraints for others. In other words, let’s consider a quantified etiquette.

Suppose you have D hours per day to spend your attention on email. For now we’ll only consider non-work email, though the math serves either way. Say you receive, on average, N messages per day. Say it takes R minutes, on average, to read an email message. Suppose that you reply to P percentage of the messages that you read and that it takes, on average, A minutes to answer those. Here are constraints for a simple attention budget, stated as an inequality:

N(R + AP)/60 ≤ D

Let’s plug in some example numbers:

N = 110 messages per day
R = 0.75 minutes to read a message, on average
A = 2.5 minutes to reply, on average
P = 12% reply to the messages read
D = 1.5 hours per day on attention for email

110・(0.75 + 2.5・0.12)/60 = 1.925 hrs > 1.5 hrs

Ruh-roh. That’s 28% over the attention budget for your physiological limits.

Taking a stab at “quantified self” metrics circa 1993 for personal email use, I presented results in a plenary talk for VR Vienna later that year. In those days before Gmail and filters, somewhere in range of low hundreds of incoming messages per day email became unusable. Not what early VR enthusiasts wanted to hear; they yearned for hugely mediated experiences en masse 24/7. These days with filters, my email experience hits a threshold more in the range of high hundreds per day. Given a certain level of media profile, those limits get hit quite often. Again, YMMV. The point is that there are physical constraints. Something’s got to give.

Keep in mind that this budgeting isn’t limited to email. If you’re going to model your daily attention budget, then your “message bucket” must include chat, texting, calls, hangouts, tweets, DMs, etc. Numbers become especially alarming once you start to include group chat, such as Slack — unless your organization enforces really effective and innovative policies against chat misuse. Most won’t.

Of course, some claim to be highly effective multitaskers, therefore exempt from constraints modeled above. Those same people have been scientifically proven to be full of it: generally more susceptible to chasing shiny objects, often rather adept at convincing others about how much they’ve accomplished when in fact they haven’t. Then there are corporate execs who insist they are highly effective multitaskers: more of same, though dangerously so. Have someone call security?

The foregoing issues insinuate a deep incivility and an array of conceits. Perhaps your email is merely filled with trivial cat pics and witty memes. No big deal. OTOH, perhaps you depend on email to earn a living. In any case, who’s driving? You are. Practice civility in your messaging. Those who don’t increasingly preclude themselves from the next economy — more about that later. Etiquette for email sets expectations for social behaviors for people who won’t be precluded from your attention.


At one point during a business meeting in 2015, when I’d been triple-booked and “required” to be in two other meetings at the same time, both at different physical locations … I received urgent messages on multiple Slack instances, on Google+ chat, Skype, SMS texts to two different phone numbers, messages to three different email accounts, a Twitter DM, LinkedIn mail, and private messages on Facebook. All for work, ostensibly requiring some response. Plus an incoming call from somebody who was on the G+ Hangout for the first meeting. IIRC there was also something urgent getting buried deeply into a GitHub comment thread. All during about a five minute period. Seriously? Enough!

People who engage that way, who expect to engage that way are stupid. I hesitate to use that word, though in this case its word senses fit. I’m patient in some ways, but do not suffer fools in media theory and practice.

What really got me was when a customer, for whom I had contractual obligations, used LinkedIn mail to make an important request about our project. The customer knew better, had my work email address, but used LI anyway — later saying it seemed convenient. Our project got in trouble because of missed communications. Caught some hell for that.

So I wrote a note to warn people off trying to reach me in all the wrong ways: “Don’t Send Any F*cking Email” on LinkedIn.

Reading subsequent comments and even more direct, pointed backlash… many headhunter types and other freeloaders got really pissed off. Guns-blazing furious. However, a couple friends who are highly professional recruiters (1) asked whether other engineers felt similarly; and (2) sought advice for how to handle email with better etiquette. Ergo this missive.

In sum, douchebags became much douchier, while reasonable people became more thoughtful. #winning

Some people correctly parsed my LinkedIn note. A postmodernist filter, if you will. A call for like minds to band together. Becoming the antithesis within the thesis, or the territory within the map. Kudos to you. That note really truly actually is a simple instruction for how to reach me, if you need to.

Ancient Internet History

Thirty five years plus, circa January 1981. Someone handed me a password slip with my account for the mainframe, then instructions for how to access email. Per regulations, US Army. That’s when I started using email, daily, for work. And didn’t stop. At first through ARPANET, then later my 1980s office walls sported maps for how to navigate through Usenet, public gateways hosted at major IBM centers, FidoNet, etc.

Moving into the 1990s, silos emerged and people grew more baffled. For example, bOING-bOING in the early years held a kind of writers group at first on CompuServe, then we were on The WELL. Surprisingly, many people in either of those early communities understood that they were the Internet. No one else. In other words, in a silo. Meanwhile, MSFT famously discounted the importance of the Internet until an abrupt about-face in 1995. Very strange.

Through the “early years” I’ve ran/moderated three large-ish email lists. The first was the Mac User Group at Bell Labs (circa 1987) — which ATT execs nearly shutdown in a punitive move, until Brian Kernighan told them he needed it for work. Another was FringeWare (circa 1992) — which grew into one of the first online bookstores, plus a subculture media collective, plus a performance space, plus… And then another was Dead Media (circa 1998) — on behalf of a few (in)famous science fiction novelists who shall remain partially anonymous. Great times, learned a bunch, which included getting pranked by Robert Anton Wilson, and more than one misguided and uneventful federal investigation.

Moderating lots of email for thousands of people on those lists was a great way to notice certain patterns recurring. In particular, the vehemence of headhunter types and other freeloaders on LinkedIn is nothing new. It’s a pattern seen several times before. A faint noise recalling the dying last gasps of other faded empires online. The industrial screech and clang of silos being dismantled.

MSFT Acquires LKND

Circa 2006 I got invited to become a co-founder for a short-lived tech start-up called HeadCase Humanufacturing. Aside from becoming one of the first few 100% cloud architectures based on Amazon AWS and an early adopter of Hadoop, we also scraped social media to build AIs based on NLP of public dialog. Or something. One tangible outcome was our market research, circa mid-aughts, of the emerging social networks. There were many. I recall that out of 30+ which we profiled every single one offered its own email/messaging system as a key feature. We began to get the sense that social media was merely a workaround for bad email — or vice versa.

LinkedIn exemplified the field within our 2006 study and later became one of the largest successes. Their social network was ~3 years old by that point, and already quite well established. Internal email features were essential to the product. Great peeps have produced amazing work at LinkedIn: commercial recommender systems circa 2006, excellent information sources, premier examples of early data science teams, etc. Those accolades don’t necessarily extend to the company’s audience.

During a keynote talk in Austin in Jan 2015, I’d predicted an impending doom for LinkedIn. Much corporate debt, prolonged flight of talent, plus an increasingly nastified audience of anything-goes headhunter/spammer types. About a year later, their stock dropped 44% in one day. Boom!

Four months later, Microsoft acquired LinkedIn on 2016–06–13 for $26.2 billion. Game over.

To me, two key indicators had heralded LNKD’s downward spiral long before Wall Street took notice:

  1. They built a skyscraper in downtown SF. The act itself exudes hubris. Almost no firm ever builds a skyscraper without subsequent restructuring of the business.
  2. They cap the number of bad actors whom one may block, while omitting an opt-out for their messaging system. Even for paid accounts. Seriously horrible UX and potential legal liability for any owner with less lawyers than, say, MSFT.

The email part stood out especially. Blatant lack of filtering, tagging, anything to preclude email overload. IMO, that was totally deliberate, insinuating a deep incivility and an array of conceits.

Glad that Microsoft busted a move. It’s likely a positive change for LinkedIn, plus a great property for Microsoft to adapt/absorb into Outlook, Skype, Yammer, Bing, etc. Certain silos will get dismantled, while others get created.

The overall challenge is that we each have limited attention budgets. Some bad actors — in or out of your organization — may attempt to take advantage. Some of them may find themselves excluded in the game to come. When we have personalized AIs running in lieu of today’s clunky email filters and ad blockers. Which side of the walled garden do you prefer?


"In the loop…" https://derwen.ai/

Paco Nathan

Written by

evil mad scientist https://derwen.ai/paco ; co-chair https://rev.dominodatalab.com/ ; lives on a tiny orchard in Ecotopia



"In the loop…" https://derwen.ai/

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