How to Escape Email Hell

Disclaimer: I’m an outspoken critic of email. It’s rife with dangers*, much too intrusive**, and creates too many opportunities for miscommunication***.

I also love email. Adore it, in fact, for its ease of use and convenience. In many ways, it’s an ideal work tool. It’s a love/hate thing. I wager most lawyers feel the same way.

So the big question: why don’t we do anything about it?

My last post touched on how collaboration platforms take important communication out of email—a very good thing on many levels. But I know that for most lawyers, adopting such a workflow isn’t likely to happen. Thus, this post is for those who need to break some bad email habits—but aren’t quite ready (or may never be ready) to go all-in with a platform that eliminates most email from daily work.

Perhaps promising email nirvana is over-selling. But I guarantee swift and measureable improvement if you commit do doing just three of the following things. Don’t look back. Just do them. Today. And keep doing them every day.

Some ways to escape email hell (and in the process break some bad habits), in no particular order:


There’s a reason that all productivity experts say this in every blog post ever written about email: because it works. You cannot and will not be optimally productive (and likely therefore satisfied) in your work if you don’t structure your workflow to support your productivity.

Schedule specific times in your day to check email. And only check email at those times. Let the world know that you check your email according to a schedule. The world will respect this. Why? Because you’ve set a clear expectation and you honor it.

Allowing email to constantly interrupt your workflow is allowing email to rule your workflow. Email is not work. It is a tool for getting work done and should be wielded accordingly.


No, this does not directly conflict with the above directive. By respond immediately, I mean that when you check email, respond immediately to emails that require a response. Immediately answer those emails that require nothing further of you (e.g. confirming a meeting time). For emails that do require further action, still answer immediately by letting the sender know you’re working on it and will respond by X time/date. Take the extra few seconds to send this kind of email and you eliminate the nagging emails you get from people who have yet to hear back from you. And doesn’t it annoy you when you send someone an email asking for something and they don’t respond for days? Yes. It’s annoying. Don’t do it.


If you’re done with the email, delete or archive it (depending on your system; because you have a system, right?). If the email requires follow up, then note this by starring/flagging it or sending it to your follow-up folder or using whatever method works for you. Your goal: get it out of your inbox and into the next step in your workflow. Strive to designate your inbox solely for emails awaiting response. I call it “inbox active.” Because “inbox zero” is a myth.


Hitting “reply all” and sharing something intended for one person with an entire group is one of the worst email sins. Amazingly, I see it happen on a regular basis. Make it hard to commit this sin by disabling the automatic “reply all” in your email platform. Further, think about whether you need to hit “reply all” at all, even for innocuous emails. Does everyone on the email really need to receive your reply? If not, don’t send it to everyone. Send only to the person(s) who really need to receive your email.


This is a hard one for many lawyers. Effective emails are ones that are brief, to-the-point, and easily scan-able. Yet also contain exactly the right amount of information. Too brief and you end up getting follow-up emails asking for more information. Too long and people don’t read your email. (Really, they don’t.)

The solution? If you’re sending a lot of information in a single email, break it up using bold and/or bullets with clear summary topics so recipients can easily scan and understand the content. And if you need to convey a whole lot of information, then send a series of emails organized by topic. Yes, this creates more email but also increases the likelihood that recipients will read what you’re sending by at least 100%, and therefore respond accordingly. Presumably your goal in sending an email is to convey information and/or elicit a certain response. So draft your email to make it as easy as possible to achieve these goals.

Also, remember that many people (including lawyers) read email on a mobile device. A long email that isn’t designed for scan-ability isn’t going to get the attention you desire. So draft every email anticipating that the recipient will be reading it on an iPhone.


Making email as easy to respond to as possible is priority #1. So if an email conversation shifts subject matter, don’t keep replying to the same subject chain. Change the subject line to reflect the actual subject, making it more likely that recipients will respond timely and accurately.


Do you draft a similar email over and over? Then create a template to use. My example: I often send worksheets for clients to complete, which means I type the same set of directions for completion over and over. Except I don’t. Because I have a handy template and use it, instead. The easiest options for creating template emails:

  1. Create and save it as a draft, which you can then copy/paste as needed or,
  2. For Google Apps users, save the email template as a canned response, to be inserted as needed, or
  3. For Outlook users, create a template. (Note: I haven’t tested the Outlook method).


Your workflow should make it easy for you to connect email to your calendar, your projects (cases), and your contacts. It should require one step (or two at most) to transfer information from email to the appropriate place. Work should never live in email. By this, I mean that important information on a project sent via email should be incorporated into your project management system, and not left dangling out in your email platform indefinitely. Likewise, a meeting set via email should immediately be sent to your calendar. The same with contacts—once it hits your email, it should be transferred to your contact management system.

Many platforms exist to make this connection easy and instantaneous. Explore the platform(s) that currently support your work to accomplish this. And if the platform can’t do it easily? It’s time for a switch.

So which three of the above are you going to adopt today? Share your experience in the comments—as well as any of your favorite tips for breaking email bad habits.


*Dangers include (but are not limited to) the unintended “reply all,” the temptation to discuss confidential information and think it’s actually protected, the misplaced reliance on disclaimers in email, and such.
**Email is ubiquitous — it can reach you at any time, day or night. And anywhere, thanks to your mobile device.
***Absence of tone in email almost guarantees that your message will be misconstrued (which is why you should pick up the phone if the message is important); and it’s much too easy to dash off a quick email without thinking through the consequences.

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