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Email Superpower 1: Subject Lines

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Fans of instant message apps like Facebook Messenger and WhatsApp, as well as promoters of group messaging apps like Slack, have no ability to create a subject heading for a message or series of messages.

This is debilitating far beyond how it may first appear.

If you start a one-to-one message with a contact on one of these apps, your entire history will be one long contiguous thread.

Major disadvantages of this should be apparent to any serious (non-casual) user of these formats.

Replying to older messages in Messaging Apps is Messy and Difficult

First, replying to older topics is almost impossible. While some modern messaging apps like WhatsApp, Telegram, and iMessage, allow you to reply to an older message (which then brings the older message back to the most recent message, along with your reply), it is far from ideal. Imagine someone sends you a travel itinerary and asks your opinion once the formal conference schedule is published. Two weeks later, you have the schedule and will now reply. Questions arise: will you go hunt for the old message and long-press to reply, or will you (more likely) send a new message that says, “Here’s the conference schedule. What was your itinerary again?”. Will you even remember that this “task” is outstanding since the original message has scrolled up 47 screenfuls by then? If you needed to find it, how easily could you? (More on searching in a minute).

No Topic Lists in Messaging Apps

Second, you have no list of message topics. Sure, most messaging is transient and vapor-like by default. While many messages have no long-term task-related or archival purposes, for more serious or business use, messaging apps have limited options here.

Searching Messaging Apps is Impaired without Subjects

While we would all like to believe that “full-text” search is the cat’s meow of the modern internet, the polite way to counter that notion is that it’s actually a feature designed by lazy programmers. Okay, maybe that wasn’t so polite.

Full-text search is a commodity and dozens of code bases and third-party tools exist to make it almost trivial for app developers to add this “feature”.

But without subject lines, it can be like searching for a needle in a minefield.

Sure, we would all love to believe that our lengthy message thread with our boss is quickly searchable by unique words, but that isn’t reality. In fact, the longer the thread, the more likely certain words will appear dozens, perhaps hundreds of times, in causal texting conversation.

Example: your boss often talks about QBRs (Quarterly Business Reports) and your top client, JustUseEmail, commonly abbreviated JUE. Throughout dozens of messages exchanged per day with her, you are trying to find a message from a few months back where she announced that “in a few months, the QBRs for some clients will change to monthly” (yes, effectively making them MBRs, but don’t rock the boat and point that out). You can’t recall if JUE was on the list, what date the change took place, and other important details. Because you were busy that day, you glanced at it and failed to save that message.

(As an aside, this is another weakness of messaging apps; messages are designed to disappear into the archive unless you pro-actively “save” them for future reference or action, even though sometimes you can’t know for sure it’s value in the moment, a moment often drowned in a sea of other instant messaging distractions and noise. Email, on the other hand, has the opposite design; it automatically keeps everything in your inbox for reference or action until you decide to archive it. Despite some feeling “overwhelmed” by this approach of email, it’s actually a major benefit).

Time to search your messaging app. You start with “QBR”, “change”, and “monthly”. That brings up 97 results. The word monthly is in everything, it turns out. So you hunt down the rules on Boolean searches (if your app allows it) and you try “QBR” AND “change” AND “monthly” and after a few false positives, you find the message. You’re no programmer, but you had to become one to find a single message.

Except none of that happened. Because if you’re like most so-called knowledge workers you’ll either (a) ping your boss another message asking if she can resend her first message, or (b) send an @here message to the team chat asking everyone else if they remember when the monthly QBR change is happening and if JUE was on the list of affected clients.

Messaging Apps are Transient; Serious Communication is Emailed

All of which proves the ethereal nature of instant messaging apps and, despite the hype and marketing claims of companies like Slack, their never-ending penchant to create more messages on the same exact topic, not less. After a certain point, most messages add little value, but instead are a demonstration of the frailty of the messaging system.

A few miscellaneous thoughts.

iMessage has Subject lines, but don’t get excited

iMessage introduced subject lines about three years ago. No one uses them and they are all-but useless. Perhaps Apple has some long-term ideas here, but for now enabling subject lines for individual messages merely adds a bolded line above the rest of the message. This might be slightly helpful to a recipient, particularly if you need to send several long-winded messages in a short time period. But there is no way to see a list of messages received (or sent) by topic, nor is there any indication that Apple places greater weight on subject headings over body text when searching for messages. For now, the feature is largely cosmetic.

Twist at least understands the superpower of subject lines and knows they are needed

Twist, a popular Slack alternative, uses named conversation “threads” in their channels. This is very close to email subject headings and is perhaps one of the better implementations of the concept of naming topics in a messaging app. While it certainly lacks many of the other superpowers of email, it beats Slack’s subject-less threads hands down. In fact, Slack introduced threading as a response to competitors like Twist, but failed to allow for named topics. In Slack, one is still forced to read the whole introductory message to determine the nature of it before deciding to click the (very tiny) “replies” link. Contrast that to Twist which puts the topic loud and proud and those curious to read more can click anywhere in the box to jump into the thread. It’s a workable alternative for fast-paced group messaging and it surprises me that more organizations don’t ditch Slack for Twist. Perhaps Salesforce’s acquisition of Slack will bring some deeper corporate features into Slack.

Slack Message Find-a-Thread Salary Swap

I had this idea at an office that a Slackbot could be created that would track salary swaps, $5 at a time. If someone posted a question on a Slack channel that someone else was able to find in a prior Slack conversation, the poster would lose $5 and the finder would gain $5. Admittedly, this is socialistic wealth transfer, but with reason and purpose. I was told the idea was illegal and would also be “unfair” because some people are “just really good at searching”, apparently missing the point that without incentive, some people would never become even mildly competent at searching and instead be forever dependent on those that were. After working there a while, I also realized that it was most of upper management that couldn’t find messages in Slack (or even emails sometimes), and so the salary swap would affect them disproportionately. I don’t think they were worried about the money as much as the potential embarrassment (e.g., “CTO James Slatherton lost $120 two months straight”). As for the illegal part, I simply thought it should also be illegal to bother (harass) a dozen or more colleagues for information previously recorded. But I’m not naive; the vast majority of offices do this all day long. Slack and other messaging apps just make it even more likely. Email isn’t perfect, but somehow messaging apps seem designed to create more chaos, not less.