Many of us seem to have a love/hate relationship with email. You would think that after 40 years of sending electronic mail (yes, email was invented in 1971!) we would be experts at it, but that’s simply not the case. Most of us don’t give any more thought into the emails we send than the phone conversations we have – and why should you? Well, that may be part of the reason why your emails suck.

While email has been around for many years, the mechanics of sending email really haven’t evolved. We compose and send one message to any number of recipients in the To, Cc or Bcc field and assume that our poor grammar, weak humor and first-grade sentence structure are ignored and our message understood.  It’s a wonder anything ever gets accomplished this way.

Email is an imperfect mode of communication but if you are simply aware of the challenges, you can start reprogramming yourself to send better email.

The following concepts may help you understand why your email may not be as effective as it could be. If you’re cognizant of them while crafting your mission-critical emails, you’ll have a much better chance of getting things done the first time around.

1. Expressing Tone is a 50/50 Game

There’s a Dilbert cartoon where Tina the tech writer is upset with Dilbert for sending a “rather brusque” email and would like an apology. Dilbert responds that he’s sorry she doesn’t understand what brevity looks like and the ensuing discussion goes downhill from there.

It’s a wonderful illustration of the complexity of human behavior at work and how each of us might interpret both the function and tone of an email differently. One of the most important things you can remember when sitting down to type your email is that people interpret emails based on their current state of mind and not necessarily in the tone intended by the sender.

According to research published in the Journal of Personality and Social Psychology, people tend to misinterpret the tone of any given email 50% of the time. And perhaps not surprisingly, those same people thought they were correct 80% of the time. 50/50 odds are horrible in any scenario, whether you’re trying to close a deal or convince a group of people where to go for lunch.

An easy way to avoid the 50/50 gamble is by simply avoiding unnecessary emotion in your email. That may not always be possible or practical so if you find you’ve got to express your emotions, always request a call or in-person follow up as soon as possible. Left alone, misinterpretation of tone can result in the single biggest time and productivity killer.

2. Recognize That Relationship Disparity Matters

If we think of email communication as flat, it’s not hard to understand why it fails us in so many circumstances. Let’s say you’re the HR manager and you send a follow up email to a recent interviewee. You were less than impressed with them but want to keep your boss in the loop of your progress so you add her in Cc to the response.

Now, you’ve sent one message to two different people, both of whom have very different relationships with (you) the sender.  This phenomenon doesn’t really exist in live conversation and email tends to fail us here. The sender understands both the disparity and intent clearly but his recipients may not. That becomes painfully clear when your boss reaches out directly to the candidate for a follow up interview because she thinks this was your intent in Cc’ing her.

So why do we add people to the Cc and Bcc fields so often? Perhaps it’s because we think it minimizes our own liability in a given or maybe working as a team mandates it. In either case, without context, people added to an email will always have some degree of relationship disparity and are at risk of being unaware of why they’ve been added or what’s expected of them.

A good rule of thumb is to give a moment’s thought to everyone you’ve added to the email and ask yourself, what is this person’s relationship to me and what information do they have (or not have) that will allow them to respond accordingly.

3. Structure Matters

I’ve given a few presentations about email effectiveness and I like to point out the 50/50 rule above because it tends to makes people think. One day, a manager from one of the large email vendors mentioned to me that while it was true, people do tend to misinterpret tone, some people are simply poor communicators.  In other words, some of us simply can’t string the words together to save our lives.

It’s hard to quantify, but it’s no surprise that poor communication costs businesses millions of dollars in lost productivity, but because even the highest levels of management are guilty of it, organizations will function for years without addressing it. Let’s be real, who’s going to tell their boss her email skills suck?

So this part is for you executives – if your emails re not structured properly to begin with, if you’re not taking into account relationship disparity, tone or structure, then you’re making it much harder for you and your team to succeed.

Ignore structure and you will wind up spending additional time adding context to your existing email. And if you respond to one bad email after another, without structure or context, you may find yourself in a never-ending vortex of email hell. In other words, a Dilbert cartoon.

4. Depth is for Writers; Email is for Communication

Very few of us write professionally for a living (myself included), and while it may seem a simple thing to string a bunch of words together and communicate the thoughts and ideas swirling around in your head, professional writers know better. A writer might agonize for hours over sentence structure, a word, a concept or the simple placement of punctuation.

Think of all the facial expressions and vocal inflection you use to provide context in natural conversation.  Emotions such as sarcasm, anger, optimism or fear can be easily misinterpreted in a “rather brusque” email and wind up being interpreted differently than their original intent.

The reality is that in business, we sometimes don’t have the luxury of time so most of just let loose and let the chips fall where they may. You can stop the madness before it starts by thinking carefully when drafting an email, and make sure you’re sending the right message to the right people. If the concepts you’re trying to convey are complex, always suggest a call or in-person meeting to articulate the full opportunity, proposition or issue.

After practicing the concepts above, there are a number of useful plug-ins and add-ons for email clients that can help you send better email. But remember, no matter how good your tennis racquet is, if you don’t practice your serve it’s still going to suck!

What a great event this was! CTIA 2010 was really our first public event after launching beta versions of both the Outlook plug-in and BlackBerry application and the feedback I received has been invaluable. Press reviews have also been fantastic and LAPTOP Magazine, who first covered our public beta for Outlook , gave us a Best of CTIA award for our new BlackBerry app as well as a really smart review! We are all very grateful and so excited to be making cool products that help the way people communicate with one another.

While there I had a chance to speak to journalists and bloggers from all over the world, and the Bccthis concept really seemed to resonate (I now have a whole new bag of feature requests to take back to our team to review). While CNET pointed out the lighter side of our application, IntoMobile highlighted the time saving attributes. And over the next few weeks I think you’ll see others continue to post stories about what Bccthis means to them – and that’s really exciting for all of us to see.

I have to say, I was a little nervous doing all of these on-the-floor 2 minute video interviews but everyone was so passionate about the space that I’m already looking forward to the next show.

And what will Bccthis be showcasing next time? Stay tuned because we have some cool new features we’re working on as well as expanding our support for other platforms so we can help everyone improve the way they send email.