At some point in the last year there was too much email.

I’ve considered myself a competent manager of email and to-dos for much of my career, but the quantity of email that needed my attention exceeded a heretofore unknown ceiling and I began to understand how the smallest parts of my inbox policy could have a large affect on my reputation.

In this piece, I’ll explain the flawed system that worked nicely me for decades, how I detected its failure, and the new system that I’ve built that is currently keeping me sane.

A PRE-EMPTIVE ASIDE TO THE GTD NERDS OUT THERE. Yes, I know David Allen wrote this phenomenal book 12 years ago that would have saved me a lot of pain, but as an engineer I am afflicted with a wonderful disease called “Not Invented Here.” This disease forces me to ignore the helpful advice of others. It requires me to often build my own tool when there are plenty of pre-existing tools already built. You may think this disease is inefficient, but I find it educational. If GTD is your life blood, you will likely find little value in the piece, so go read this amazing Nobel Prize acceptance speech.

Decades of Email

My email system has been simple by design. What I discovered over the years is that whenever I added unnecessary complexity to my process, I also tended to create more work than productivity. Years of following this simple design resulted in the following setup:

All mail is contained within my inbox folder. This should set off all sorts of alarms for you. Of course, you have too much email, Rands – it’s all in your inbox. Calm down. I’m a professional. The “every mail in my inbox” policy is accompanied by the following rules and assumptions:

Aggressive pruning of noise via mail rules. To increase the signal of my inbox, I’ve developed a set of mail rules that pull non-essential emails into sub-folders. Noisy mailing lists are a primary culprit. By pruning out the noise, the probability of an email in the inbox being useful is higher. This includes rules like:

Automated highlighting of important emails. With a good chunk of the noise removed from my inbox, important mails tend to have a small handful of similar characteristics, and these characteristics are captured in additional mail rules:

• Mails from humans I care about.
• Mails with me and only me in the To: line.
• Mails with me in the To: or CC: line.

Within whatever email program I’m using, these types of mails are highlighted in some fashion so I can know at-a-glance that they are likely higher in priority.

The last two rules aren’t rules, but assumptions. My traditional inbox strategy made two large assumptions:

Search in mail works. With everything sitting in my inbox, search must work effortlessly. I must be able to remember, “Who said that thing about the thing?” and run a search and reliably find the appropriate email.  

To-dos can be equally tracked in email and a productivity app. In hindsight, it seems like an obvious flaw, but I’ve always worked under the assumption that I can track a follow-up equally well within email (via flags or other tagging mechanism) as well as within my productivity system, which for years was Things until I recently moved to Asana. In general, smaller tasks that lacked subtasks would remain in email, whereas large tasks would land in the productivity system. More on this flawed assumption shortly.

For years this system has worked. You can look at those simple rules and assumptions and easily find structural and systematic flaws. But even with those flaws I’ve had a modicum of success in my career, and this flawed system kept track of important projects, kept me in touch with my teams, and kept me in the know for many years. Your system is likely better, fancier, and more efficient, but I had proof my system worked. Until last year.

The Little Things

First, an important word about priority. I use the following system to prioritize work in my head:

• P0: Heinous. Must be handled immediately. Top of the list. Major repercussions if not resolved promptly.
• P1: Important. Needs to be handled soon. Major repercussions if not resolved, but not heinously on fire.
• P2: Somewhat important. Likely sans deadline. No one foaming at the mouth. Still needs to be finished in a reasonable amount of time. This is the majority of the work in the world.
• P3: Nice to have. Someone somewhere needs this to be done, but if doesn’t happen, we’re likely ok.

With my rules and assumptions in place, my inbox routine was:

• When I had time for email,
• I would read everything that was unread, and,
• If I could act on it immediately I would (mostly), but,
• If the next step was too big for the moment, I would either move it to the productivity system or leave it in the inbox for future consideration.

There are three kinds of email:

1. Useless crap
2. Information for later use
3. Actionable in some fashion.

At my historical usual arrival rate of actionable mails per hour, this process works. Checking email every so often, I would use the unread flag as a means of understanding both whether I’d read the mail and where I needed to act on them. Actionable (read: easy) P0s and P1s were crushed. Larger high priority issues were often pushed to the productivity system for longer term tracking. Lower priority issues remained in the inbox for short-term handling. Rinse. Repeat. Mostly everything handled… for years.

At a substantively higher arrival rate of actionable mails, the system fails in both obvious and devious ways:

• At a high rate of actionable email arrival, this system is unacceptably lossy because the inbox is growing at fast rate. P0 issues and P1 issues were mostly being handled (keyword: mostly – keep reading), but those P2 and P3 issues were dropping at an unacceptable rate. Does this mean I was prioritizing incorrectly? No. It was ok for a few of those P3s to drop and even some P2s, but when the majority of these fell through, the message I sent to the world was: lossy.

• Search in mail is fine, it’s my brain that sucks. On top of the exploding inbox was the fact that I believed I could keep all of the state and context of my inbox in my head, and if I couldn’t, I’d search. Again, that works at a certain arrival rate, but when the inbox explosion occurred I was no longer really reading all the mails. Which meant I didn’t have context, and more and more often searched my inbox for things I didn’t know. Inefficient.

• Unread doesn’t mean shit. In a time of inbox explosion, the unread flag doesn’t mean a thing. It’s the smallest piece of useless data. All it says is, You were here at some point and maybe you did something. I really don’t know. I would furiously get through my unread mail, chasing the fake goal of getting to zero unread messages… like it meant something. It doesn’t. Again, inefficiency.

It is the combination of all these unscalable flaws that is the most damning and obvious failure. As it became clear that my tried and true system was no longer working, I worked harder… using the same system. This meant that as the email continued to increase, I searched more – poorly. I started to try different tagging mechanisms. New folder and inbox strategies were adopted, then dropped, and all this thrash did was exacerbate the core problem: lossiness. What was a steady loss of P2s and P3s transformed into the loss of P0 and P1 issues, which leads us to the final rule:

Everyone knows when you drop a P0.

Inbox Close-to-Zero

As a leader, you define your reputation all the time. You’d like to think that you could choose the moments that define your reputation, but you don’t. They are always watching and learning. They are always updating their model regarding who you are and how you lead with each observable action, no matter how large or small.

Your inbox policy is full of observable action. How quickly does he respond? Did she read the whole mail? Who did they CC:? Why does he sign some mails, but not others?

Each micro-transaction I performed in my inbox had the ability to collectively affect my reputation as a leader. Worse was the realization that if P0s could fall through the cracks, how many P1, P2, and P3s did I drop? The answer is a painful “a lot.”

With these two punches to the stomach in mind, I rebooted my inbox during the holidays with these fixes. Some are essential and some are personal, but I believe all are valuable.

1. Anything more than ten or so emails in your inbox might as well be a bajillion. I now practice inbox Close-to-Zero. As each email arrives, I act if I need to and then I archive and if I can’t act immediately, I determine if I am likely to act today. If the answer is yes, I leave it in my inbox. If the answer is no, it moves to Asana and is then archived.
2. Stop hoarding. Start archiving For mails where I don’t need to act, I read the whole mail and move it to my archive folder. If I can’t read the whole mail, but need to, it stays in the inbox. Otherwise, the mail is sent to the archive. The goal with both this and the previous rule is to decrease cognitive load. I should be able to look at my inbox and have a good understanding of what is important today. Not yesterday, not a week ago, but today.
3. Use conversation/threaded view. I’ve turned this feature on and off in my various email clients over the years, mostly because of a perceived performance hit when it’s enabled, but it is now remains permanently on. With my aggressive archiving policy and piles’o’email, the conversation view gracefully brings back all the context I need when I invariable dig into my archive to refresh my memory.
4. A strict to-do transfer policy. As I alluded to above, the protocol by which a mail becomes a to-do is well defined. Just about everything that can’t be acted on immediately is placed in the to-do system, except for a short list of mail that I’ve planned to handle that day. If those mails exist at the end of the day, they are moved to Asana. No exceptions.

Small Heroic Acts of Efficiency

Your day as a leader is full of very small decisions. Speak up in that meeting? Embrace serendipity and talk to the random person in the hallway? Answer that email? These very small decisions collectively send signal to the company regarding who you are and what you believe. Your team is watching you – always – because you are their leader.

An efficient inbox policy doesn’t make you a good leader. In fact, it’s expected. Whether you like it or not, progress often stalls while they’re waiting for your response. You, as a leader, have the ability to create a huge amount of organizational consternation simply by not getting completely through your inbox efficiently on a daily basis.

As a nerd afflicted with “Not Invented Here” I like to architect and build systems from the ground up because I tell myself that I like to learn, but I’m often simply stubborn. Uh, I could build that. This stubbornness unfortunately often makes me beholden to the things I build because, well, I built them. As a leader, I need to be willing to throw away cherished things that aren’t capable of evolving with me and I need to listen to the helpful advice others so I can better focus on getting shit done.