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Published on May 1st, 2006 | by cdadmin

The Bad In Email (or Why We Need Collaboration Software)

A few weeks ago we wrote, about The Good In Email
and why email is still the most adopted collaboration tool around. The
response to our article was mostly positive, peppered with a few
negative jabs here and there, but overall we were pleased with the dialogue it invoked in our industry.

quell any speculation that we are ditching collaboration software in
favor of email, realize that this was just an exercise. We embarked on
a close examination of email to see what we could learn from this
killer app, in an attempt to improve our customer’s experience. Our
examination included an inquiry to all sides of the medium; with the
intention of extracting the good and throwing away the bad.

spite of email’s universal success (as a collaboration tool), and in
spite of its many good traits, email contains deep, inherent flaws that
force users and markets to seek alternatives to collaborating via

After all, if email is so “good” at its job, then how
do we explain the popular resurgence of Collaboration Software (masked
as Web 2.0)? And how else do you explain Ray Ozzie as the CTO of Microsoft?

reiterate our stance from the previous article, the facts speak for
themselves. Email is here to stay. But while ubiquity might define
adoption, ubiquity does not define ‘correctness’ ‘rightness,’
‘goodness’ or even ‘efficiency.’ Yet another example where the ‘wisdom
of crowds’ does not apply. Just because ‘everyone is doing it’ does not
mean that everyone should be doing it.

Therefore, we’d like to present The Bad In Email, or Why Ray Ozzie is the CTO of Microsoft.

Email is Silo’ed
The single worst trait of email is that it’s silo’ed.

I mean by silo’ed is that email traps information into personalized,
unsharable, unsearchable vacuums where no one else can access it – the
Email Inbox. Think of your Email Inbox as a heavily fortified walled
garden. Not mentioning the difficulties many have accessing their Email
Inbox outside the corporate firewall, the Email Inbox contains a
hodgepodge of business, personal and private information that most
people do not want to share with others.

For many folks, the
Email Inbox contains their most intimate secrets all mashed together
into a single location: business correspondences, contracts, proposals,
reminders, tasks, love letters, indiscreet online purchases, dirty
jokes, pictures of your spouse (and kids), time-wasting games, inappropriate messages from co-workers and friends and lets not forget spam.

think its obvious that silo’ed data is devastating to team
productivity. The snowballing effects of silo’ed data can debilitate
even the strongest of project managers.

Here is the progressive snowballing effect of silo’ed data:

1. The data and content types are mixed and mashed (see list above).
2. The data is often ‘NSFW’ (Not Safe For Work).
3. The data is unintelligent (untagged, lacks taxonomy, unfiled).
4. The data is therefore unsharable. (both by personal choice and lack of technology)
5. The data is therefore unsearchable (by others).
6. The data is therefore inaccessible (by others).
7. Your Email Inbox is therefore *useless* to the rest of the Team (In
spite of the goldmine of data that probably resides in your Inbox).

Email *Perpetuates* Many Walled Gardens
The only thing worse than one walled garden are many walled gardens.

soon as you introduce two or more people into a collaborative
environment, you now have multiple ‘my inboxes’- each being a walled

There are some hack fixes to this problem: Yahoo Groups, Google Groups,
Newsgroups, List Serves, Forums, Carbon Copy and Email Aliases (ala
Exchange); but in the end, each of these solutions still rely on the
Email Inbox to send and receive data. Thus reinforcing the Walled

I can’t tell you how many times I’ve posted to a
Public Forum / Group expecting to continue the exchange online…only to
receive an email IN MY PERSONAL EMAIL INBOX.

the Walled Gardens of our Email Inboxes are deceivingly warm and cozy.
This feigned-comfort of safety whispers into our ears like a wily devil
to, “Just email the document to me” or “Just email that document to
yourself” with the false-belief that it will remain safe, secure and
locked away. But that is just it……its locked away so that NO ONE ELSE
CAN ACCESS IT. This is counter-culture to team collaboration.

false-pretense of comfort in email only reinforces and perpetuates the
temptation to build and protect your own walled garden.

Email is NOT Secure (Part 1)
We’ve been lulled into believing that email is safe and secure.

If you are using SMTP (the universal pipe, remember?), you need to know that it doesn’t encrypt data/messages.

If you are using POP or IMAP, you need to know that they both require you to send unencrypted authentication (username/password).

both the email Sender (you) and the Recipient are using Digital
Keys/Signatures, the contents of your email are about as secure as
Imelda Marcos in a shoe store. While the idea of using Digital
Keys/Signatures sounds neat, it is not practical.

Outside of fictional characters in Cryptonomicon, I’m not aware of anyone else using encrypted email and digital signatures.

(Anyone using cryptographic e-mail is in the minority and the exception to the rule.)

I’m aware of services such as Hushmail, and certificates offered by Thawte and Verisign;
but I’ve never received a Hushmail nor have I ever encountered an email
that I couldn’t read because I lacked a Digital Signature.

If you still don’t believe me, and if you are a user of Outlook, try this:

In Outlook, click on Tools | Options and select the Security Tab.

select either of the first two check boxes that ask you to “Encrypt
contents and attachments for outgoing messages” and/or “Add digital
signature to outgoing messages.” Now, send an email.

If you did this correctly, you will be prompted to see this screen.
If you are brave, click on the “Get Digital ID” button. If you are like
me (and I venture that most of my audience is comprised of technical
and/or business users) I don’t have the time, patience or desire to
venture down the path of buying certificates and keys and configuring
them on all six of the machines I work from on any given day.

This is a non-starter. No one uses this feature. Thus, my point: Email is not secure.

will concede that webmail is semi-secure in that if you are using SSL
(HTTPS), the transmission of data from your computer to the email
server is secure. But the moment your message leaves your email
host….its a free-for-all for any one to sniff and hack. The contents of
your message are not encrypted or secure…..unless the recipient of your
email is also within the confines of the secure environment (for
example, if you and your recipient are both sending and receiving email
through Gmail’s
web interface and both using SSL, then the message should be encrypted
from point to point.) But, we are not all using Gmail either (at least
not yet).

[Eudora Security Flashback: I still don’t know what the hell Kerberos is and what it has to do with a dog much less my email?]

Email is NOT Secure (Part 2)
argue that email is the single most vulnerable point in any
organization’s security policy. It takes two seconds to send a
confidential document to anyone or any group in the world. And, unless
you are using Novell Groupwise (gulp) there is no way to ‘retract’ your email.

companies spend a fortune locking down their IT infrastructure. This
results in either Total Lockdown, also known as Paralysis whereby no
one can do anything without a password, passkey, keycard, signature and
sheet; or in No Lockdown, also known as Free-Love-Utopia
whereby everyone is equal because everyone is an Administrator.

measures are very important for organizations at all levels, but they
shouldn’t prevent the free flow of information amongst a team.
Unfortunately, this also means that confidential data is only as secure
as any person using email.

Group Email is Really Complicated
personal email is easy to setup, configure and administer. Group email
is a complete nightmare. The rise of spam, phishing and viruses makes
group email administration a full time job (department in many cases).

many enterprise users the infrastructure is already there. But for the
remaining 25 million businesses in the United States that do not have
an established group email infrastructure, the cost of administration
is daunting.

Email is Not a Document Manager
company, department, workgroup and team has fallen prey to Document Hot
Potato. This is when team members call each other (or even worse, email
each other) looking for the latest revision of the

There are some interesting solutions emerging over at Nextpage and Echosign,
but these solutions are supplementary to email. They do a good job of
integrating email into the workflow of contract and signature
management, but appear to ignore the fundamental requirements of teams
to just share, search and access documents and files.

Email Communications Do Not Correspond Priority
If everyone used Outlook (70% of Central Desktop
users use Outlook), then the ability to assign priority to each message
would actually work. But we don’t live in a Microsoft world (in spite
of what many of you might think) and instead, we usually measure and
weigh the importance of an email message by the number of people
included in the carbon copy. This is highly subjective and fails to
address the need to order and sort messages and task by importance.


Email is inconsistent
spite of email’s universality, there is still discrepancy and lack of
consistency in reading HTML and rich text formats. Email clients
require users to determine whether or not to ‘download images’ or
‘convert to text,’ these are options most users do not know how to set
or configure.

How many times have you read email through a
webmail interface that reformatted the HTML into unintelligible
garbage? How many hours have you spent trying to open up a

Email works most of the time, but
when it doesn’t it’s usually the result of a Client Configuration
problem, not a connection problem.

Email is not permission based
You either have rights to use email, or you don’t. There is no viable middle-ground here.

Spam Filtering is better, but still not good enough
still find very important messages in my Spam/Junk Folder. While I’m
glad my Spam Filter (Gmail) is working most of the time, it’s not
perfect, and often requires frequent ‘gardening.’

Email does not work well for multi-users
still challenging for multiple people to share business email accounts
(i.e. support, bugs and sales messages). IMAP sort of works, but
presents its fair-share of limitations.

Companies such as Sproutit are working on solving this problem. I wish them luck and admire their ambition.

Email is Prone to Viruses
There is no need to elaborate here.

Email makes us lazy
face it, we all like being whispered to in our ear. We enjoy listening
to that wily-devil of compromise that tempts us to “just email the
document to myself.” This is purely the seduction of sloth.

the end, the strength of the collaboration tool is only as strong as
its weakest link. It only takes one person to break the entire system.

Yes, there is good in email; but it’s mixed with a bunch of bad.

In spite of our comfort with email, we must unlearn what we have learned, open our eyes and acknowledge The Bad In Email.
Email IS the most adopted collaboration tool; but it isn’t the best online collaboration tool. There are more efficient ways to work and its time
for us to let go, create and adopt collaboration tools. I know this.
You know this. And Bill Gates knows this (which is why Ray Ozzie is the CTO at Microsoft).

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