A 5-Second Hack That Every Entrepreneur and Employee Should Implement Immediately

Don’t wait until an embarrassing or costly mistake forces you to learn it the hard way.

My panic-stricken heart abruptly stopped beating, and a downpour of fear-induced sweat emanated from my armpits, instantly staining both my white silk dress and the cashmere cardigan I wore over it. Within a millisecond, I transformed from qualified new hire with a spotless reputation to the office idiot, treading on the thin ice that was my probationary period.

Somehow, in between firing up my brand-new work laptop and mulling over the perfect response to my manager’s email request, I made a giant, credibility-shattering blunder. I got so far as typing “Hi Matt” in a draft reply before a ghost gave my mouse an unexpected push and sent that email out the door and into my manager’s inbox.

“Hi Matt” — that is all.

In some professions, an accidental or incomplete email reply may not be such a big deal. Being one of the select few entrusted with representing the elite Mergers and Acquisitions division at a renowned investment bank is a lot less forgiving. If I couldn’t even send a proper email to my manager, how could they ever trust me with direct client interaction, for which millions of dollars were on the line?

Realizing the gravity of my error — this being the first post-hire impression I’d be making on our team — I scrambled to right the ship before my manager could open the message. I saw him down the hallway, leaning against another VP’s glass office, engrossed in a deal-related chat. This was my one and only window, and it was only a matter of minutes before he’d pull out his Blackberry and tend to the blinking red light that was his email notification.

Unfamiliar with the new email interface on my company-provided device, I frantically started clicking around for an “unsend” or “recall message” option. Matt’s conversation was coming to a close — he was on the move, heading towards his office.

I estimated a remaining 90 seconds before he either checked the Blackberry notifications or reached his desktop, at which point he would be confronted with my communication flub on his massive dual monitor screens.

If this was Gmail, Yahoo, or Hotmail, I would have been screwed. In fact, if it was any email outside our company’s secured intranet, my message probably wouldn’t stand a chance at being recalled.

Gmail may not have been my friend, but thankfully Google was. I followed the instructions a 30-second Google search had churned out, and finally, the “recall message” button appeared from the dropdown. I clicked “recall” and requested a success or failure confirmation, expecting the worst.

Message Successfully Recalled.

No way.

Matt had made it to his glass box of an office, sat down at his desk, and immersed himself in the content on his screens. He clicked a few buttons, started typing, and then made a phone call, utterly unperturbed. There was no indicator that he’d read or received my email. Could the recall really have swooped in as my 11th-hour saving grace?

Apparently, it did. But if it weren’t for our closed internal email system and company-wide intranet, I didn’t stand a chance. From then on, I would never again let an accidental keystroke determine my fate.

The two things that matter most in work and business

Whether you’re an employee or an entrepreneur, your success hinges on two things that have little to do with your aptitude.

1. Reputation: What people think of you is a huge determinant of the success you’ll achieve and the opportunities you’ll be afforded — and in theory, this is something you can largely control (or try to)
2. Communication: Even if you aren’t working in a sales capacity, your effective, professional, and well-received communication skills will be integral to your performance and achievements

Unfortunately, a communication blunder (like mine with my former manager within my first half-hour of employment) can have devastating and permanent impacts on your reputation. While you can only make a first impression once, tanking that flawless reputation can occur at a million different times and places, with so little as the click of a button.

I’ve sent 37 million emails in the last 18 months, and I still mess up

You might suggest that diligence and slow, thoughtful execution are the antidotes to such professional communication faux pas. As someone who’s sent 37+ million emails in the last year and a half to over 700,000 prospects, you’d think I — of all people — would have a grasp on professional communication. I must have graduated from my “Hi Matt” days to being an email perfectionist who hasn’t erred in years. Not so.

Today, I sent a very standard response — one I send manually to select new VIP customers. I reread the draft email at least three times — it was mostly copied and pasted from prior messages sent to other VIPs, so a triple read-through was likely overkill. I hit send. Then, within a couple of milliseconds, I hit “unsend”. I forgot to mention one minor thing that was specific to this VIP customer. I hit “send” again.

As I reviewed the message in my outbox, one giant mistake stuck out like a throbbing sore thumb. The subject line was wrong! Instead of “Re”, it should have begun with “Reminder”. Like lightning, my mouse shot over to the “unsend” button one final time. I fixed the subject line, hit “send” for the third time, and allowed a full 5 seconds to pass by as the email shifted from my outbox to my sent items. It was finally done.

My 5-second hack had saved me again.

The one button to rule them all

If you’re frantically searching for the “recall message” button or Googling how to claw back a message sent to an external provider — say from Outlook to Gmail — you’re already too late. You might as well accept the consequences of your faux pas and pray your recipient interprets the intended response, rather than whatever embarrassing spin autocorrect put on your chosen lexicon. There is a simple solution to mitigate the likelihood of these errors and to diminish the finality of the “send” button altogether.

“Undo send” is a setting I’ve employed for years, and it’s saved me a boatload of embarrassment and probably prevented a few lost sales. The “undo send” setting allows you to select a delay period of up to 10 seconds — I’d say 5 at a minimum, but after my triple “unsend” scenario, I’m upping mine to 10.

In those 5 or 10 seconds after sending the email, it hovers in your outbox, allowing you a few more moments to catch any final errors you may have overlooked. There’s something about seeing the email in your outbox, counting down the remaining seconds until it leaves forever, that instantly elevates your attention to detail.

You forgot to copy their business partner. You meant to request a “read receipt”. You didn’t update the subject line you borrowed from another client's response. You called them a “she”, rather than a “he” due to a mindless copy/paste job.

You can send tens of millions of emails, and you’ll still make the most obvious, avoidable errors from time to time — I’m living proof. That said, a five- or ten-second grace period gives you a welcome second chance. That simple “undo send” button temporarily lowers the stakes while lighting a final fire under your butt as you complete one last eagle-eyed read-through.

You can hit “send” and hope for the best, letting the chips fall where they may, or you can buy yourself a bit of cushion that just may be your saving grace.

5 seconds can make or break your reputation

Most people don’t get a second chance to make a first impression. My professional reputation could have gone up in flames the moment “Hi Matt” left my outbox. In any other scenario, it probably would have, and relying on a successful post-send “message recall” is like playing Russian roulette with your fragile reputation. I wouldn’t suggest it.

A flubbed email these days can easily cost me on the low-end between $500 and $2000. On the high end, it could threaten my company’s reputation and cost hundreds of thousands of dollars. No matter how sure I am of my message or how many times both my assistant and I have reviewed and revised it, I’ll take a free 5- or 10-second safety net any day. When professional communication can easily make or break your reputation, peace of mind is worth the minor delay.