How I work: Staying on the offense with email
With the use of a handful of helpful tools and techniques, I’m able to ensure that no email can slip through the cracks.
Email is awful. It’s a beast of a technology that’s thirty years old and definitely doesn’t conform to most of how the world operates today. But no matter how much we decry its antiquity, unfortunately it’s still the primary way that business communication happens.
Unsatisfied by the way that my own email was getting accomplished, I wanted to make a dramatic change. Every morning I’m presented with a seemingly endless amount of stuff to reply to, and it never felt like I was getting anywhere – just swimming against a neverending torrent.
But over the course of the last few months, I’ve developed a workflow for myself that finally makes me feel like I’m able to get out in front of the insanity. Something that gives me the thought that no matter how inundated my inbox can become, I can stay on the offensive. Below are the tools and techniques I use – hopefully they can be of some use to you as well.
Tool: Gmail & Google Apps
Obviously I can’t talk about the tools without mentioning my mail provider of choice. Google seems to always be leaps and bounds beyond other mail providers in terms of the technology they’re developing. Unfortunately some organizations still find the need to use Exchange & Outlook – to the unfortunate souls required to use things other than Gmail I say this: “I’m dreadfully sorry.”
Please keep in mind that most of the tools that I discuss below require Gmail.
Technique: Treating your inbox like a “to do” list
I’ve found business email to fall under three typical categories: actionable, conversational, informational. Here’s how I treat them:
Actionable
This is a “to do” list item. These kinds of emails are messages where a certain action is required to be performed. I will either choose to perform that action immediately, or defer it to a later date (more on how later) – depending on the nature of the action. Sometimes I’m “blocked” from performing this kind of action – such as in situations where I’m waiting on someone else to accomplish something. In these cases I either “star” the item, or use a timer to return it to my inbox when the required items might have been received. One could also put these emails in a “waiting” label or folder. Boomerang and Mailbox are tools that help me manage this “to do” list of email – both are described below.
Conversational
Just like it sounds – these are ongoing discussions where there isn’t necessarily any action that needs to take place. I like to use email to communicate as opposed to instant messaging in a lot of circumstances because I’m able to have these conversations asynchronously. This way they don’t interrupt my day, or my workflow. These kinds of conversations I’m able to defer for hours at a time while I’m getting other things done.
Informational
Informational emails that are confirmations that something got done, or situations where something is simply needed to be known. They will typically come up for me when I am wanting a report on the completion of a task, or something similar. Informational emails will rarely require a response, but in some cases a response may be necessary for clarification, or confirmation of receipt.
Tool: Sanebox
Sanebox does exactly what it proclaims in its namesake – keeps your inbox sane. Essentially it does what a junk mail filter would typically do, except it’s non-destructive. Sanebox will run through your inbox and identifies emails that seem to be newsletters, transactional emails, and the like, and moves them into a Gmail label. This effectively improves the signal to noise ratio of your inbox and allows you to focus on a specific subset of your unread messages. Gmail’s “important” filter does something similar, but I’ve almost always found it to be far inferior to Sanebox’s.
Each time you receive a message that SaneBox thinks is noise, it applies the label “SaneLater” and moves it away from your inbox. If you don’t think it should be there, just move it back to your inbox and remove the label. This begins to “train” the behavior of the tool.
One way that I’ve altered SaneBox’s behavior is by changing the “SaneLater” label to “[Mailbox]/SaneLater.” This makes it so that I can use SaneLater’s functionality inside of my Mailbox iOS app. Note: Mailbox doesn’t natively support Gmail labels, so this hack is necessary to display labels from within the app.
Technique: Don’t constantly check and send email
It’s an easy trap to fall into, but you should never constantly be checking and responding to your email. Email is asynchronous communication and you should be thankful for that.
One side-effect of always quickly sending a response to email is that you’re possibly giving the impression that you don’t value your own time. Unfortunately you’ve now set the expectation to the recipient that you’re a fast responder – something that could hurt you when you don’t take a similar action in the future.
Rather than attempting to consistently stay on top of the deluge, I choose to do my email at specific intervals. This is typically four times a day for me:
Morning/waking up
This is triage time. I go through my inbox and make sure that I’ve deferred any email that didn’t require immediate action in the morning.
Start of my workday
Now I can take action on all of the email that it makes sense to. I’m also likely going to start sending out new emails at this time.
Post-lunch check-in
Again, this is a triage moment but in some cases I’ll take a bit more action on the inbox than the morning typically.
End-of-day
At this time, I’m attempting to get my inbox to zero as much as possible. This includes deferring emails that don’t need action right now, or trying to take final action on things that require my immediate attention.
Tool: Boomerang
Let me start by saying Baydin’s Boomerang is awesome. Before Mailbox ever existed, Boomerang would allow you to “snooze” messages and bring them back to your inbox later. It’s a plugin for Chrome, Safari, and Firefox that sits inside of the Gmail (or Outlook) interface. While I’m viewing any particular email, I can choose to defer that email based on a set of instructions, as shown in the graphic to the left.
This plays into the “email as a to do list” concept quite nicely as it allows me to defer emails to a specific date.
One of the best parts of this interface is the “Only if nobody responds” option which does exactly what it describes.
The other fantastic part of Boomerang is that these same options exist for outgoing emails. This is one of the main components of my “staying on the offense” with email. The gist is that whenever I send out an email, I can flag it to be returned to my inbox on a specific date, with or without a reply somewhere in the meantime. So, if there’s a particular ask of me by someone in this email, I can make sure that it will return to my inbox at the corresponding date so that I might take that action.
In other circumstances, it allows me to follow up with important messages that may have gone unnoticed by the recipient. I recognize that not everyone is as a crazy with their email as I am, so sending friendly reminders to respond isn’t something that I consider bad behavior.
In the above example, Harper asked me to follow up with him in the event that he didn’t get me a message by a specific date. This is the perfect use case for Boomerang.
Tool: Mailbox
By now, I’d be surprised if everyone using Gmail and an iPhone hadn’t heard about Mailbox. It’s a fantastic app where you’re able to use quick swiping gestures to archive or defer emails, similar to Boomerang. This makes for super fast triaging of an inbox. They’ve even got this clever graphic (seen at the top of this post) that displays when you’re at “inbox zero.”
The only unfortunate bit about this is that the overlap between Boomerang’s and Mailbox’s functionality is pretty high, and they don’t easily work with each other. I’ve just dealt with this discrepancy. Unfortunately one aspect of Mailbox’s deferment feature is that you’re not able to set “if no reply” like in Boomerang – something that is sorely missed.
Now with the addition of the iPad version, I’m able to blaze through my email and make sure I get to actionable emails quickly by triaging those that don’t matter for that moment – even on the go.
My secret sauce: “No Response” Gmail Plugin
NOTE: I’ve updated my method here and you can find an explanation below.
A while back I recognized a problem in my own email workflow. Many times I would send an email that didn’t have the Boomerang “return to inbox” feature enabled, that never got a response. This doesn’t even account for the countless emails I’d send in Mailbox which doesn’t have this feature. I’d get even more frustrated because eventually I realized that Gmail had no search that did the following: “Show me email conversations where I sent a message, but got no response.” After sending out a tweet, inquiring about said funtionality, Baydin’s CEO Alex Moore wrote a Gmail script that would perform this kind of search beautifully.
His original “NoResponse” script would be a one-time action that searched the last 7 days for emails with no response. This was the start of something big. I ended up modifying the script to search for email every one day, applying a Mailbox app-friendly label, and making sure that the script ran on a schedule once per day.
Check out Alex and I’s magic “No Response” script.
The next step after installing the script is applying a timer to it. That can be done through the Google Script interface by clicking “Resources” in the menu bar, and then going to the Triggers for that script. Once editing the triggers, you can set up a “time-driven” event trigger that takes place once per day (I chose 6:00am).
Update: I’m now using a service called Unreplied. It’s a paid thing, but one advantage that I’ve found with it is that it’s always correct. It constantly scans and if there’s ever a reply, it removes the “No Response” label that it’s been given. My previous method would often show false positives since it wasn’t continually checked.
Post-send reminders
With this script enabled, if an email doesn’t get a response sometime in the time period I’ve set up, it gets labeled with “No Response.” Now, once a day I go through that filter and make sure that I’ve either applied a Boomerang timer to it, or use the Gmail keyboard shortcut “Y” to dismiss that label. It’s one extra step that I’m needing to take when going through email, but it’s something that makes sure I’m always able to stay on offense.
Conclusion
These tools and techniques aren’t for everyone, but they’ve worked wonders for me. Previously I would miss email, forget to respond to things, send out important messages that garnered no response, etc. Not anymore. It’s so much easier to stay on top of my inbox with this workflow now, and I’ll never go back. Though I do wish that Boomerang and Mailbox would simply combine forces (along with the “No Response” feature) because that would be unstoppable.
Epilogue: Some additional tricks & tools
HelloSign
HelloSign is a tool where I’m able to sign contracts and documents right from my Gmail inbox, all without leaving that interface. It saves me from the tediousness of printing off a document, signing it, scanning it, and sending back. Instead, signing documents are as easy as a couple button pushes with it.
Rapportive
It’s pretty common to receive email from people that you don’t know. That’s where Rapportive comes in. It sits alongside your email messages and shows you the profile of the person that’s emailed you. By searching LinkedIn and other places, it’s able to put together a comprehensive view of who’s communicating with you. Another nicety is that you’re able to hit one button to search all correspondance with that person.
Gmail Labs: Send & Archive
Within Gmail labs, you’re able to add a “send and archive” feature to your compose window. This means that within a single action, you’re able to get an email out of your inbox as soon as the email is sent – a feature that’s been super crucial in my attempt to speed up my emailing.
Gmail Labs: Undo Send
Have you ever made a mistake in an email, or inadvertently emailed someone you didn’t mean to? Of course you did. That’s where Gmail’s Undo Send comes in. It adds a buffer of time after pressing send where the email doesn’t actually send, and gives you an opportunity to “undo” that action. I’ve saved myself some serious embarrassment sometimes because of this.
