LTRC Roundtable: Email Inbox Prioritization

Our Panelist:

Debra Bruce (DB), Michael Eisenberg (ME), Sarah Gold (SG), Allison Johs (AJ), Alan Klevan (AK), Alexander Paykin (AP),

How do you prioritize your emails, especially when dealing with a high volume of client communications, court notices, and internal correspondence?

DB: I flag emails with a reminder date/time. I can also drag them to the Outlook Task icon or the Microsoft To Do icon to set up a reminder and instructions.

ME: I find that color-coding e-mail senders help a lot.  In your preferences (Apple Mail, Outlook, etc.), you should be able to color code recipient’s e-mails automatically.  So, when I get an e-mail from a judge, court clerk, or notice from a court, they show red.  Client e-mails appear orange.  Internal e-mails appear yellow.  I can usually eyeball important e-mails quickly. There can be an issue when I get a non-color-coded e-mail as it may be for the first time, I am receiving an email from that party or junk e-mail.  But as I have a method for dealing with junk e-mail, see my discussion of SaneBox below, it gets easier with the remaining e-mails over time.

SG: I do have folders for reply, forward, review, and do.  If I have an large number of emails and no time to deal with them individually, I will sort them quickly to come back later.  Otherwise, I will flag individual emails in Outlook.

AJ: One of the best ways I’ve found to prioritize my emails is to keep my inbox as clear of other “junk” as possible so that I can see and address important email messages. That includes ruthlessly unsubscribing from lists that no longer serve me, blocking email addresses, and using rules and folders to separate less important messages. I also try not to look at my email constantly. Instead, I look at it periodically throughout the day so that I can focus on addressing those important messages.

It's easy to go down the rabbit hole with email – by the time you’ve finished addressing what was there, new messages have arrived. I try to put a limit on the time I spend on email before I go back to working on something else.

AK: I prioritize every email I receive.  The way I do this is by creating a “time map” in my practice.  I devote one hour a day (either a full hour in the afternoon or 30 minutes in both the morning and afternoon) to review my emails with no interruptions.  My email inbox always ends the day with one page of emails, no more, as it is known that emails on successive pages rarely get acted upon.

AP: I make it a point to (a) create contacts for every email account that important things might come from, be it clients, opposing counsel, court notifications and the like; (b) set up rules to make sure that the emails that are important pop up on the important portion of my Gmail interface, which tends to work fairly well; and (c) I also have various conditional formatting rules that add flags, tag emails to my practice management system, and forward them to additional staff members as appropriate.

What e-mail program do you use? Are there any particular tools native to your e-mail program that you use to help manage your e-mail inbox?

DB: I use Outlook in Microsoft 365. Microsoft 365 includes the To Do app, which aggregates tasks captured from many different input methods. For example, I can drag emails to the To Do app in the same way that one can drag emails to the Task icon in Outlook to create a task with the content of the email in the task body and a due date and reminder date.  Inside To Do my tasks can be sorted into appropriate lists I created based on my needs. The lists might be based on the type of task, the due date range,  or for a particular client matter. If, however, all I actually do is flag the email in Outlook, all of my flagged emails automatically show up in the To Do app in the “Flagged Email” list.  With To Do I have multiple ways to get reminded to get back to that email.

ME: For work, I use Apple Mail.  Natively, I like the ability to color code e-mails based on who the sender is (see discussion above).  Apple Mail now has a feature that allows you to “send” e-mail later.  This is great for when you are working on the weekend or after hours.  Sometimes, you don’t want the other party to know (whether it be opposing counsel or your client) that you are working on a weekend, late at night, or early in the morning.  This feature allows you to have the e-mail sent on a day and time of your choosing, e.g., Monday at 9 am when the workday starts.

SG: I use Outlook, but no specific tools beyond that.

AJ: I use Outlook. One of the tools I love in Outlook is conditional formatting. I use conditional formatting to color-code email from important senders so that they stand out in my inbox and I can see immediately which messages I need to address. I also use rules and folders to automatically move messages to folders, and in some cases, to automatically archive or delete messages in specific folders.

AK: I use Outlook.

AP: I use the professional custom domain version of Gmail. All of the things I mentioned in response to the first question are built into that version of Gmail and it further uses various forms of AI to self-identify emails that it thinks are important and pushes them into the important portion of the inbox by itself. Whenever it makes a mistake, I tag the email is not important so that it learns for the future...

Do you use any plugins, or third-party software solutions you find indispensable for managing your email more efficiently?

DB: I use Sane Box to automatically move certain types of incoming emails out of my Inbox and into the Sane Later folder or the Sane News folder. Those are emails that are low priority, but that I still may want to read at some point. The Sane Later function “learns” whether to leave emails in my Inbox or sort future ones coming in from that sender to Sane Later based on whether I drag email from that sender to Sane Later or back to the Inbox.

SimplyFile is another Outlook plugin that I have used for many years. It learns which Outlook folder emails from a sender usually get moved to. After I open an email, the SimplyFile box in the Outlook ribbon offers several suggestions of likely destination folders. I click on the appropriate suggestion or “other” to  choose the correct Outlook folder and the email gets filed in that Outlook folder.

ME: My favorite third-party software solution is SaneBox. It works with your e-mail provider (not directly on your computer), where you train it to handle certain e-mails automatically.  For example, if it’s a junk e-mail you never want to see again from that sender, drop the e-mail into your @saneblackhole folder and never see it or e-mails from the sender again.  If it’s an e-mail in your inbox that you are not ready to handle at the moment and want to deal with later, i.e., reappear in your inbox, SaneBox has some SaneBox Snooze features you can use: Some examples are @SaneBox3h (for having the e-mail reappear 3 hours later), @SaneBox5pm (for having the e-mail reappear at 5PM), @SaneBoxtomorrow (for having the e-mail reappear tomorrow morning), @SaneBoxnextweek (for having the e-mail reappear next Monday morning), etc. SaneBox also has other great features like Sane Do Not Disturb, where you can turn it on when you are away from your devices, at night or over a weekend, when you are on vacation, or at any time when you need solitude from inbound emails and have them reappear at a time and date of your choosing like when you get back from the weekend or a vacation. There is also Sane Reminders, where you can put a “reminder” email address (e.g., [email protected], [email protected], etc.) in the CC: or BCC: field. SaneBox will track this email and put it back into the top of your Inbox at the time indicated unless the email has been replied to!

SG: I use the Clio Plug-in to sort read mails into the client files as needed.

AP: Not many anymore. I used to use Boomerang, but over time Gmail built-in all of its most useful features natively. I also used to use a plug-in that would pause the inbox so that I would stop looking at new emails and focus on the work I was trying to do. However, I found it was preventing me from finding out that something urgent happened, and I realized that I do better with the distraction than the not knowing. I do use the plugin from my practice management system so I can tag email directly into it and record time without leaving my inbox, but that's just about it.

Do you use any email automation or rules to filter, sort, or flag important messages?

DB: Historically I found that Outlook limited the number of rules that I could use or that too many rules slowed Outlook down. That’s why I started using SaneBox and SimplyFile. The Outlook rules issue may have been corrected by now, but I have been happy with the SaneBox and SimplyFile plugins.

ME: See answers #1 & #3, supra.

SG: I do in my personal emails, but not in my business account. 

AJ: As indicated above, I use rules to filter and sort messages. For example, most newsletters I subscribe to are sent to a separate folder. That gets them out of my inbox, and I can review them when I have time.

AP: Absolutely. I rely on conditional formatting rules to do all sorts of things in terms of automating email processing, tagging it to cases in my practice management system, forwarding emails to relevant parties as needed and whatnot.

How do they integrate with your existing legal practice management software?

DB: A number of practice management software programs have an Outlook plugin that makes it easy to send a copy of an email to be stored in the client matter file of my choice. I have used a number of different practice management programs over the last 20 years. Clio and MyCase store the emails in a form that resembles the original Outlook text. Others might also now, but they were among the first that I identified that did that saved emails to the case file with only 2 or 3 easy clicks.

ME: Integration is an important feature of why I have been using Daylite for nearly ten (10) years.  Daylite, through a company called Marketcircle, is a Mac OS-based program that works only on Mac Computers and Apple iOS devices.  It has a “Daylite Mail Assistant” that integrates with Apple Mail (note that due to some new security measures Apple recently implemented into its Mail program, there have been some recent growing pains.). The DMA allows you to tag the e-mail into Daylite. Tagging includes contacts, projects, tasks, and calendar appointments, inter alia.  This is great because when I look at the client/project/task/calendar, etc., in Daylite, I can see the e-mail traffic behind it without needing to open my e-mail.  Further, I can create tasks and assignments with deadlines directly in my e-mail via DMA that will appear on my staff’s Daylite assignment screen. This way, they can see the e-mail related to the project they have been assigned and can also see the entire e-mail history to the entire project without having been cc:ed on earlier e-mails.  This is great for new staff or staff that have not been on the project before. Additionally, Daylite has an iOS program with its main function baked in.  So, I can keep my work e-mail separate from my personal e-mail while on the go and have access to both my work e-mail and my law practice management program remotely.

SG: The Clio plugin sorts my email into individual client files.

AP: The integration with my practice management system is excellent. I am able to tag all of my communications so that they appear in the communications tab within the matter on the practice management system, I am able to enter time and even assign tasks without ever leaving my inbox. I can also set entire email threads as related to a specific matter or client, making them visible to all of my staff without them having to have been copied on the email.

How do you delegate email management within your team or firm?

ME: Management of e-mail in and of itself is not “delegated”.  But tasks related to e-mails are assigned through Daylite as discussed in #5, supra.

AP: Everyone at the firm follows the same rules as I do and we are all able to see each other's communications via the practice management system. We also have an administrative counsel from which I could search all emails and where an archivist maintained, even of the deleted emails.

Are there any collaboration tools or practices you recommend for ensuring important emails are addressed promptly by the right person?

ME: See Answers #5 & #6, supra.

AP: Assuming your practice management system is like mine, I would suggest setting up automated notifications to the responsible attorney whenever anything happens to a matter. That way, if someone other than the responsible attorney on the matter is involved in any communications that pertain to that matter, the moment they tag them into the practice management system in their inbox, the responsible attorney will receive a notification and be instantly made aware of the new activity. He or she can then assign next tasks in the matter as appropriate.

Do you have a system for organizing emails when you file them outside your inbox to ensure that important legal documents and correspondence are easily retrievable when needed?

DB: I use the MyCase plugin for Outlook to save a copy of the email and attachments into the relevant case file. If I have created a relevant Outook folder, I can then use SimplyFile to also quickly save the original email and its attachment to the relevant Outlook folder.

ME: No. My e-mails are tagged into Daylite.  I can either easily generally search Apple Mail or categorically search Daylite for the e-mail.  The e-mail in my inbox goes to my office e-mail folder, filtered out as junk by SaneBox or filtered into other SaneBox mailboxes like Sane Later for generic membership or solicitation e-mails that I don’t need on my desk and can casually deal with later!

SG: I do have a number of other non-client folders in Outlook which allows me to easily reference emails on my phone or laptop.

AJ: I organize email messages just like any other documents in my practice. They get filed where they would be stored if they had arrived in any other format. If they are related to a client matter, they are saved in the client’s file.

AP: Yes. In addition to my inbox, where nothing important is ever deleted and is archived until the end of time, or at least until the end of the firm, as mentioned previously, all important emails are tagged into the practice management system, so a separate copy ends up being maintained there, where it is accessible to all staff who are assigned to the particular matter.

Achieving E-mail In-box “Zero”: What is your process to reach this place of Zen?

DB: Candidly, I’ve never been there.

ME: Sadly, I believe the concept of “Achieving E-mail In-Box ‘Zero’” is fiction. Getting through multiple e-mails throughout the day so that your e-mail inbox is “empty” is a worthwhile goal.  But it is unrealistic.

Unfortunately, everyone, including lawyers, let alone myself, tends to treat their e-mail inboxes as a to-do list. We have a mindset that an e-mail must be responded to immediately.  And since it is simple to file it away and accidentally forget about it, we naturally think we should substantively act on it now.  I think the secret sauce is not worrying that an e-mail is substantively responded to immediately.  But instead, administratively handled appropriately (in a shorter amount of time than it would take to substantively respond to an e-mail) at a later date.

That is why I like Daylite.  After I have already automatically triaged my e-mail with color coding, I can tag it to the appropriate person (which Daylite does automatically in most cases [based on presets]), tag it to the appropriate project, calendar anything necessary, and add a task with a due date & assign the task to myself or staff then move it out of my e-box knowing it has been addressed.  And for those e-mails that I am not quite ready to deal with them, but I know they're important, I use SaneBox Snooze.  The trick is not to achieve “In-Box” Zero but to know that your e-mails are addressed administratively in a timely manner regardless of the e-mail count in your inbox.

SG: Ha! It's only a dream. It'll never happen.

AJ: I’m not sure that “Inbox zero” is entirely possible, but I try to keep my inbox as clear as possible by moving anything out of my inbox that doesn’t belong. For example, I’ll move an email about an event to my calendar, or a message that I need to save to the client’s file or to my filing system, and then deleting the message out of my inbox.

In addition to the methods I discuss in my other responses above, I also periodically clean out my inbox by sorting by sender and/or by date. That makes it easy to eliminate messages I don’t need.

AK: This is actually easy if you stay on the course of “Inbox Zero.”  I was taught the acronym of OHIO – “Only Handle it Once.”  The key to “OHIO” is known to me as DDD – “Do, Dump, Delegate.”  Every day, I have uninterrupted time (no calls, no peeking at the internet, no daydreaming) to address each email that comes into my inbox.  I respond to each email by taking an action on it, deleting it, or delegating it to someone else to take action on it.  If the email is important enough, I will save the email to the appropriate file.  Then the email is out of my inbox and it’s on to the next email.

 AP: First, I skim quickly through the emails that are not categorized as important by my inbox, so I can quickly select and delete all of the nonsense. Then, if I find any important emails in that area, I tag them and kick them up into the important side. On the important side, I go through each email and if it is something I can deal with right away, I do. If it is something where I am waiting on someone else, I use the snooze function to make the email disappear and come back at the time I designate so it does not clog my inbox. For anything where I would be the one doing the work but I'm not going to be doing it right now, I immediately set up a task for myself in my practice management system. At the same time I tag the email to the matter, set a deadline for myself for that task, and if I will want to easily reference the email and want it to bug me on the day that I intend to work on the task, I also snooze the email to that date. If it is an email that whatever work I'm doing on will have to be responded through, I also snooze it to that date. Using this method, once I'm done with everything I can do at that very moment and I have triaged the remaining emails to whenever is appropriate, my inbox is empty. Of course new emails come in immediately, but that's just life...