How I’ve Made Email my Secret Weapon

It’s quite fashionable to hate email. Countless articles have been written decrying how awful it is. Billions of dollars have been spent trying to reinvent it. And the latest fad is just to give up — screenshots proudly showing six-figure unread message counts and articles about “inbox infinity” abound.

I’ve become quite the contrarian on this subject. I love email. It’s my secret weapon. Some of the best news I’ve ever gotten came in an email. As an adoptive dad, I caught my first glimpse of two of my kids through an email. I’ve closed deals, hired amazing talent, and connected great people via email.

I love Slack as well, but there is still nothing better than email for connecting with the world outside, and looping in members of your team to get things done.

I’m sure there are a lot of people who get more email than me, but I’m no slouch in that department. I’m the CEO of a 200+ employee company with 20,000+ customers. It takes a full time executive assistant and a full time Chief of Staff to keep my world in orbit right now. My email address is also not hard to figure out. In fact, I put it right on my LinkedIn page.

And yet, I get to Inbox Zero anywhere between 1–3x a week.

I’ve had a lot of people ask me how that’s possible, so I decided I’d take a little time on vacation and write this post. (Yep, sharing ideas like these are my idea of fun. 😂)

Slow the Fire Hose

People talk about the messages that appear in their inbox as if they have no control over them, and that’s not entirely true. The first thing you probably need to do is turn down the flow of messages.

  • Email is for messages, not for articles. There is VERY little content that I allow to flow into my inbox. Unsubscribe from all those blogs and newsletters you subscribed to. Follow them on Twitter, or drop them into Pocket. If you can’t bring yourself to do that, think about setting up a separate email account for this stuff. That isn’t an inbox; it’s your personal magazine.
  • Be selective on marketing. There are 10–15 brands that I have a strong connection with who I’ll let into my inbox because I actually want to hear from them. Otherwise, I’m pretty confident they will find a way to get my attention in another channel.
  • Kill non-essential or duplicate email notifications. Every app and service that we use is pinging us with notifications. But a lot of time, they are non-essential, or the same alert also comes as a push notification on your phone. Either change the settings in the app, or put in some email rules to kill those.
  • Be an aggressive unsubscriber. When you get unsolicited email you don’t want, always click unsubscribe if the link is there. Most unsub systems work with 1–2 clicks.

I know people who have followed these four tips and killed an astounding 80% of their incoming messages.

Kill the Notifications

I’m decently responsive to important things in my inbox, but the only way I got there was to massively reduce the noise, so I could hear the signal.

  • Turn off all the app notifications. Email shouldn’t generate banners, unread badges or sounds. Trust me, you won’t forget that your inbox exists; you don’t need any reminders to check it. Give yourself the space to do focused work and then tap your email app when you’re ready to triage your inbox.
  • Use the VIP feature if it’s helpful. I have my direct reports and my board members on the iOS Mail VIP list, so I get a notification on my phone if one of them emails. However, the more that our urgent stuff moves to Slack or texting, the less valuable this has become.
  • Free yourself from feeling obligated to respond to everything. I’m sure I miss emails from real people that go into spam, but I also get a lot of “asks” from people I don’t know. Given that I’ve committed my time to family, company and non-profit work, spending time and attention on those is breaking my commitments to others. These emails are like people who show up to your office without an appointment — you might drop everything to give them your time, but you usually can’t. Why is an email any different?

Upgrade Your Tools

I’m a big believer that high quality tools more than pay for themselves in higher productivity. There are limits to that logic, of course, but if you can make your own tool decisions, ask yourself if having a good setup can increase your productivity by 1, 2, 3%. You can do the math on that.

  • Use an email service with great search. You need to be able to find archived messages with ease. Nobody beats Google on this front. Both my company and personal addresses are on Gmail. I have both accounts set up in Apple Mail on my Mac, iPhone and iPad because those apps work really well when offline. But if a quick search isn’t turning up the message I need, I hop into Gmail and there it is.
  • Kill all those folders. I know people who make long lists of folders for every project or topic. Guess what? It takes a lot of time to archive emails that way. I have two folders (more detail below) and I still misfile things by accident once in a while. If you use an email service with great search, you do not need 85 folders in your mailbox. Put everything in one big archive, and use search to find it when you need it.
  • Get a to-do app. Too many people use email as a to-do list, and trust me, your inbox is awful at that. What is important gets mixed in with what is new. You constantly have to re-read the email and reinterpret what you actually need to do. My favorite to-do app right now is Asana, particularly because I can hit forward on an email, change the subject line to “call Bill re: contract terms” and hit send. Bam, it’s on the list, and I can archive that email.

If you’re in a big organization stuck on an archaic version of Exchange server, or they won’t let you use a tool like Asana, a few of these tips may be a challenge for you. You should come join Riskalyze and help us empower the world to invest fearlessly instead. 😉

Set up Text Macros

I get more sales pitches, and requests for calls or meetings with VCs, private equity firms and investment bankers, than I know what to do with. These are personal emails without unsubscribe links.

If I don’t respond, I usually get a second or third email from them. So I set up text replacements on my iPhone and, to my delight, discovered they sync to my iPad and Mac. Here are my three…

  • notint = Not interested but thanks; please remove. This is short, sweet and to the point. The “but thanks” disarms the person and makes them want to be polite and follow my wishes. It used to read “please remove me from your list” but that resulted in a bunch of silly replies insisting I wasn’t on a list. Shortening it did the trick.
  • novc = I’m sorry; I’m heads down on a bunch of initiatives and don’t have time for a call right now. Maybe in a few quarters. This has worked well for VC, PE and investment bankers. I might want to talk with them eventually, but I genuinely don’t have time to invest in a call or meeting right now. They’ll email me back in six or nine months, and my answer will either change or be the same.
  • nocant = I’m sorry; I’ve already made commitments I’d have to break if I tried to make a call or meeting work right now. Is there another way I can help? The last sentence is only for those I genuinely feel like I might have a way to help, like an introduction to make.

These don’t work for every circumstance, but they’re often a good starting point, and then I edit them from there.

It’s Time to Triage

Okay, we’ve got the flow of email reduced to the messages that matter. We’ve equipped ourselves with a to-do app so we can move our tasks out of the inbox. And we’ve killed the notifications so we can stop going into our email every 30 seconds. Now we’re going to triage our inbox.

Triaging is not the same as processing. We’ll get to that below. Triage is something we can do for two minutes, even if we don’t get every message triaged. We can do it on our phones while walking down the hallway. I always scan the names and subject lines, and triage the most important messages first.

And oh yes, let’s just forget the silly myth of “touch each email only once” — it’s a nice thought, but that’s for people who aren’t busy, or can do the “I only check email twice a day” thing. The rest of us need to triage first.

Here are the actions you might take while triaging.

  • Reply. If a very quick reply is all that is warranted — like a “Thanks” or “Great” or “On it” — I’ll reply while triaging.
  • Reply with a Macro. If one of my pre-written replies works, I’ll send it while triaging. Done.
  • Forward/Delegate. I’ll delegate things that don’t need context or deep explanation. My team is very used to getting messages from me with “please handle” or “?” as my only note.
  • Process Later. The “To Process” folder is my second inbox. This is where I put messages that need more than 10 seconds of work each. I don’t have time to handle them during triage, so I move them into To Process instead.
  • Archive or Delete. If no further action is needed, I hit archive. If it’s something I don’t need, I might hit delete instead. (On the other hand, I might put it into “To Process” if I want to unsubscribe or block the sender later.)

At the end of triage, the only things left in my inbox are the deeply urgent things that I must handle on the run, before I’ll get back to my to-do list. If my CFO needs me to call the bank, or one of my board members has sent me a note that shouldn’t wait until later, that stays in the inbox to deal with as quickly as possible. Emails from your boss or up your chain of command, unless explicitly not urgent, probably belong here!

After triaging, my inbox is often empty…but I don’t consider this Inbox Zero quite yet.

Okay, Let’s Process!

When your inbox is empty, and the critically urgent is under control, it’s time to process. I always process emails in the order they were received, oldest to newest. On a good week, I might find half an hour every day to process, and be running 2–3 days behind. On non-stop weeks, I’m processing emails on a Saturday that arrived last Tuesday. Such is life.

I’m usually on my Mac, but at times on my iPad. Trying to process without a real keyboard is a waste of time, so I rarely do it on my iPhone.

Here are the actions you might take while processing.

  • Unsubscribe or Block. I talked above about being an aggressive unsubscriber, but there’s no time for that while triaging. And to whoever put me on the master list of professional real estate investors, may you be cursed with a thousand Viagra spams. 😂
  • Reply. This is when I will write longer or more substantive replies. Writing more than a few sentences requires time and thought. I’ll do that during processing. (By the way, this has taught my team something interesting. Send me a concise email with numbered options and you may get a reply in an hour. Send me an email that requires a longer reply, and you may not get a reply until the weekend.)
  • Forward/Delegate. There are also times I need to forward and delegate things that need more substantive thought and context. Processing is when I’ll write those notes.
  • Task. If the email requires me to take action, and I can’t get it done in 2–3 minutes while processing, I’ll task it. This may be “edit draft blog post” or “call Bill re: contract terms.”

For my email load, processing takes 2–3 hours a week. Your mileage may vary. But I find that this approach is way more efficient than trying to process at the same time you triage — that, plus allowing too many of the wrong messages to flow into your inbox, are what makes email feel impossible or overwhelming.

Tasks Involving Email

Rarely do I task myself to reply to an email; I just try to reply while processing. However, there are often more complicated tasks that involve editing/reviewing attachments in an email, and then replying back with those edits. So you want the email handy for those tasks.

That’s the purpose of my second folder, called “On Tasks.” When I forward the email to Asana to create the task, I change the subject line to “Review new product financial assumptions for Dan <ontasks>” and that reminds me the message is waiting in that folder when it’s time to work on that project.

Welcome to Inbox Zero

My definition of Inbox Zero is when I have my inbox and my “To Process” folder completely cleared of messages. (For what it’s worth, I also include clearing out all the Slack messages I’ve starred for a response later; I do that during processing.)

So what have we accomplished?

  • Triage clears the non-urgent out of our inboxes.
  • Processing gives us time to focus on the important things.
  • Getting to-dos out of our inboxes allows us to have a clear view of what we need to do and stop reinterpreting emails over and over.
  • Email becomes manageable and we become more responsive to the customers, partners, teammates, shareholders and friends that we care about.

May email turn into your secret weapon that closes deals, recruits amazing talent and makes you the connector of amazing people.