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

A companion piece to The Good In Email that takes an alternative view, written in 2006.

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.

To 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.

In 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 email.

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?

To 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.

What 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.

I 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.

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

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 Garden.

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.

Unfortunately, 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.

This 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).

Unless 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.

Now, 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.

[I 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)
I 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.

Most 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 sign-in 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
While 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).

For 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
Every 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 proposal/contract/document.

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
In 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 MIME-ENCAPSULATED MESSAGE?

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
I 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
Its 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
Lets 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.

In 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).

This post was originally written May 1, 2006.

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