Steve Strauss, founder of www.theselfemployed.com, tells why the "reply all" option on your email may be dangerous and how to use it carefully.

After going back and forth trying to get an answer about a potential big gig from a very busy guy named James, a good friend of mine decided he needed some help. So he tried to shoot me an email, wanting my feedback as to what he should do next.

But instead of forwarding his correspondence with James to me, my friend mistakenly hit the dreaded “reply all” button:

“Hi Stevie, This is my correspondence w/ James. Trying to get him to answer my questions.

He is barely giving me the time of day. What do I do? I thought by at least numbering my questions to him it would make it easy for him to answer. But nooooo. He seems too damn busy to even bother with any response at all. What do I do?”

My friend did get an answer to this email, not surprisingly. James’ answer, was, “What's this???? What the???” And that was the last he ever heard from James.

Death by “reply all.”

We have all done it. Sometimes the damage is fixable, often it is not, but either way, there is almost no worse feeling than sending out an email that you thought was private, only to have people not privy to the confidential nature of the correspondence be included.

The stories would be funny if the results weren’t so devastating:

  • How about the time that UC San Diego mistakenly sent a “Congratulations on being admitted!” email to 28,000 students who had actually been rejected?
  • Or the professor who shared his plans for his proposed passionate evening with his girlfriend . . . with the entire faculty?
  • Or what about the tale of the insurance company salesman who thought he was replying only to colleagues when in fact he somehow included the customer in on the email, and sent out this: “We could easily convince the customer to buy it--even though the customer doesn’t need it.”

All of this begs the question: Is there anything you can do to avoid such disasters? The good news is that there is:

First of all, if, like many people, you use Outlook as your email program, Microsoft offers a plugin that you can download and add to your email ribbon. Called NoReplyAll, the nifty app simply grays-out your reply all button. If you do need to reply all or forward an email, all you need do is click “disable” and you are free to respond as you wish. But that extra bit of caution sure can come in handy.

If you use Google’s Gmail, you can go to Settings -> Lab and enable the “Undo Send” button. Another Gmail option is to go into Settings -> General, and set a delay of up to 30 seconds before your emails go out. That may just be enough time to catch your boneheaded mistake.

But then again, maybe not.

Look, mistakes happen, but with email, they seem to happen too often. This is so I think for two reasons.

First of all, the very nature of email is that is seems like a quick way to communicate. Of course the operative phrase in the previous sentence is “seems like.” Very often the opposite is actually true – email ends up taking way to long when often a simple phone call will suffice.

The second reason email mistakes happen too often is because of (and this just may be the writer in me coming out), its seemingly casual, quick nature. Because of that, email does not seem to get the attention it deserves and actually demands. What I mean by this is that email is now the dominant form of business communication – more than the phone, more than letters, more than anything. So why then are people still writing “i” instead of “I”, or not spell checking, or simply looking sloppy?

The answer to all of it is to take your time, proofread your emails, and be vigilant. Give your email a little extra attention. Double-check the recipients. Be careful. And then be extra careful.

Your career just may depend on it.

Today’s tip: Small business optimism continues to rise. According to small business research from Dell released this week:

  • Over the course of the next year, more than half of entrepreneurs and small business owners expect finances to improve (56%)
  • Most expect better prospects for sales (75%), and
  • The majority of small business owners consider access to technology to be key to successful growth (77%).

About the Author(s)

Steve Strauss

Steve Strauss is one of the world’s leading entrepreneurship and small business experts. He has been seen on CNN, CNBC, The O’Reilly Factor, and his column, Ask an Expert, appears weekly on USATODAY.com.

USA TODAY Senior Small Business Columnist and Best-Selling Author