There’s a moment of pure horror that exists somewhere between the time that you click ‘Reply All’ and the moment you start realizing that you have actually clicked ‘Reply All’. In 2011, I experienced this very, very clearly when on a Tuesday morning, I found myself unable to do anything while my very snarky commentary about the client’s impossible to meet demands being sent not only to my intended recipient – my project manager – but to the full project team including the client.
During moments of critical situations in my life, I felt that time seemed to stretch, such was the case in this situation as well. I had a lot of time to notice my beating heart, a sudden increase in cold sweat and the weird feeling of my whole career flashing right in front of me. I had time to create a list of terrible decisions that I had made which had led me to this point, starting from choosing this profession to not disregarding the warning dialog box that had definitely popped up before I hit send. I had time to think about how quickly I would want to pack my stuff, change my name and update my resume.
One thing that I did not have with this scenario was the ability to stop the email.
When you push that button, you have sealed your fate. The virtual action is complete. Your frantic email is already tearing its way through cyberspace, ping-ponging off routers, and replicating in inboxes. The only universe where that email wouldn’t arrive is a parallel universe where you made better choices.
“For the curious: my exact words were, ‘If he asks for one more ‘small change’ to the entire architecture, I’ll suggest he build it himself with crayons and popsicle sticks since that’s apparently the level of engineering expertise we’re working with.’ Undoubtedly not my finest moment of professional decorum.”
The consequences fell upon me like a ton of bricks and happened instantly. ‘The client requested my removal from the project.’ ‘My manager scheduled an emergency meeting with the optimistic calendar entry ‘Project Communication Protocols’ which was a polite way of saying ‘Why You Shouldn’t Call Clients Crayon Wielding Incompetents.’
‘The irony of this particular disaster is that I was generally known as the careful one on the team.’ This particular quote hits hard because if you know me personally, you know that I am a meticulous person. It hurts me to say this, but I did give a-law-and-order ‘Reply all and email etiquette’ speech surprisingly less than a year back but instead strapped a cover with ‘best practices in corporate sustainablility’ hoping nobody gets me. And now I have to live with knowing an
entire room full of colleagues was forced to stau
two hours worth of listening to horror stories from me about how I straight-up embargo everybody curtly telling the rest of the room: “shut up, I don’t want to listen to you!”
This life is meant to be lived without everyone assuming you live in a world filled with inescapable cliches.
The disastrous Reply All incident I had is certainly not unique to me. Because of the nature of the work, meeting their digital atrocity falls under the umbrella of horror stories for office workers. We tell such tales almost as if they are folklore or legends, cautionary stories shared through gossip. It is common to gather as a community in the defined Slack channels and recount the chronicles of emails sent with fatal intent, ominous confirming messages sent by an overly zealous autocorrect, and documents uploaded by unsuspecting users.
Some of these stories I have collected over the years because of my fascination with the evolution of technology and its impact on communication, and in part to mitigate the guilt I feel navigating the digital world. Take, for instance, the case of the marketing executive who, in a company-wide cost-cutting announcement, shared her opinion on who should be first in the firing line in a reply all blunder. Or, the IT manager who meant to send his complaint about an HR executive to one of her peers, yet bypassed his peers and sent it directly to the entire executive team including the executive. Not to forget, the administrative assistant who shared detailed instructions for her dog sitter with the reply all function regarding a client meeting. She includes the unforgettable phrase, “If he keeps peeing on the rug, just put him in his crate. He knows what he did.”
As I have mentioned previously, ReplyAll disasater- phenomenom is purely rooted in cross generational, cross industry, and cross expertise appeal. Be it a fully-fledged technology company or an advertising firm, there are always defenders. So-called technological illiterates have also borne the Weinstein label and the list goes on. The button is positioned conveniently next to the reply button; clicking it during a moment of distraction or absentmindedly tapping the mouse could signal doom.
The mental ramifications of these occurrences follow a forecastable pathology that I have witnessed dozens of times. Initially, there is the moment of acknowledgment— that gut-wrenching apprehension of realization that something irreversible has taken place. It is followed by the frenzied expectation stage, in which the sender exhaustively attempts to either retrieve the send or concoct regret-filled follow-up messages that only worsen the situation. After hope, comes the shame spiral wherein each ping of a new email induces fight or flight. Last comes the long, tedious journey of control and reputation domage recovery.
Watching my colleagues traverse this pathway has, as always, been a mixed bag. Some take the path of least resistance: “I regret my unprofessional data points. They were informed by my company’s values as well as my best self, my unprofessional self.” Others attempt self-depreciating humor: “And this is what happens when you don’t drink coffee before emailing.” Some people utilize the ostrich strategy, never responding to the email and waiting for everyone to forget about it. (Spoiler: They don’t.)
For me, the self rescue plan was to hover somewhere between contrite and burning career bridges. I told every single one of them, I paid them off over and over again in small increments, I apologized to my boss and the client face to face, and I worked hard enough to make the breech an aside instead of the main event in my professional timeline. Alongside this, I instituted a new personal policy which I entitled the five second rule: my interaction with the email system requires a three count of the recipient list and a full 5 second hover over the send button.
We still make the same mistakes through the years of emails and videos trying to educate us because such mistakes utilize common human weaknesses. Simple tasks such as sending emails are routine and do not require extra thought. We switch contexts rapidly; for instance, we can engage in casual talk with a colleague after which we can have formal interactions with clients or supervisors. After long hours of heavily focused work, most people tend to get tired and operate on autopilot. As much as email clients have advanced over the years, it is still too easy to provoke careless verbal communication with wrong recipients.
The absolute worst cases of Reply All incidents are a combination of different factors that explode into the worst situation. The email is not only sent to the wrong person, but comes with some specific content bound to trigger each inappropriate recipient. At the same time, the email gets to the recipients when emotions are too driven and sensitive. To add to the dreaded scenario, the email discloses feelings about the person that should never have been disclosed, and thoughts that were never intended to be shared out in the open.
Not long ago, I had a colleague named Jacob who had quite the incident. His story still sends shivers down my spine. He was engaged in a very taxing project for a client whose main point of contact, to be nice, was very hard to satisfy. After several weeks of endless revision, Jacob got another email, this time, it was an enormous change request. Jacob intended to send it to our team along with his scathing appraisal of the situation. In a twist of fate, he clicked “Reply All” which meant his candid remarks about the client were shared with every single member of the client’s team.
His exact words—now a legend in our office—are: *“ Round 17 of ‘I don’t know what I want, but this definitely isn’t it’ Some one please sedate me before the next call, or I will tell her exactly where she can stick these revisions.”*
I and the rest of the team witnessed this entire fiasco unfold in real time. In a matter of seconds, Jacob’s mild frustration turned to horror in a matter of seconds. “I just ended my career,” he said softly while looking at his screen. “I just professionally immolated myself.”
Jacob miraculously survived this incident. After an emergency ‘clean up’ session with higher ups, he sent a client a rather heartfelt email taking full blame. The client, surprisingly, accepted that the process, as we all know, had been needlessly frustrating for everyone. It continued under a different project lead and Jacob was able to enforce his version of email security – a post-it note on his computer reading, “CHECK TWICE, SEND ONCE,” along with many other safeguards.
As I mentioned before, the mistake I refer to was not the error itself, but rather toward the end where he said how the incident had urged him recognize several flaws in his reasoning towards communicating with people.
“I was expressing frustrations via email that should have been dealt with in person,” he stated. “I was putting my thoughts into text that I would never verbalize face-to-face.” His Reply All blunder had revealed not just a slip of attention but an extensive pattern of conflicts that he could not navigate effectively.
I have witnessed similar revelations in other people after their self-proclaimed email catastrophes. A Reply All blunder can act as an unflattering, uncomfortable reflection when it comes to communication patterns as habits that are wished to be forgotten. The co-worker who passive-aggressively comments and distributes calls the comments ‘private’. The supervisor who, in a casual email, talks about the members of the team in a completely different manner to the one they use when speaking to them, mistakenly includes them. The colleague who sends out an email marked ‘for your information’ with an attached mail history expecting that it will not be scrutinized, loses a lot when the put-off issues finally receive the attention they deserve.
My very own incident made me reckon with my penchant for private snark—words I considered witty and harmless within my circles turned out to be unprofessional and unkind when viewed through broader lenses. I had to ask myself: If I wouldn’t want these words associated with me, why would I utter them in the first place?
Needless to say, not all Reply All nightmares stem from the aggressive editorializing. Some, in fact, are simply chaotically misplaced in their attempts at restraint. Like my former colleague who blurted out her gynecologist appointment date on the reply all function for a company-wide announcement about the quarterly results. Or the new joiner who replied all to the welcome email with “Thanks everyone! I’m so thrilled to join the team after escaping the toxic hellscape that was [Previous Company],” blissfully unaware that numerous executives had worked at that so-called “hellscape” long-placed at during their career.
Within the digital sphere, there are as many communication blunders as there are words to be said, and the ‘Reply All’ button is only the most infamous of them. I have witnessed careers being ruined by video unmute mistakes in meetings, sharing inappropriately on shared documents, or even sending messages using chat apps to wrong recipients. But Reply All blunders seem to be the most devastating — perhaps for the reasons of how far they reach, how long they linger, or because of how public they are.
In each of these instances, while the comfort may be sparse, it lies in knowing that the mistakes are undeniably human ones in a hyper connected world. They highlight the fact that beneath every professional email is a human being full of mistakes, miscalculations, and sometimes jaw-droppingly bad tech blunders. In a carefully curated world that tends to shape one’s image professionally, Reply All fails provide one with an opportunity to default to unapologetic authenticity, whether it is in reality or in action.
My personal email disaster is now a faint memory, though my coworkers love to share it during happy hours as a comedic fable. The client had another technical lead who worked better with her. My boss used as an example during my performance evaluation as “Communication Gaps in Professional Interactions” which I considered rather benign. I’ve put in place several personal strategies aimed at preventing this from happening again.
To this day, I never click “Reply All” without a moment’s pause, requiring a trace of remembered horror. Some lessons bear weight. And while lying awake at night when my overactive brain is helpfully fixed on replaying my most cringe-worthy life moments, email still cracking my knuckles, forehand-wrist sneaking out my hand, still makes the highlight montage.
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