There are lots of different email strategies out there (and it’s quite a reflection on the world we live in that mastering email is a key element in becoming more professionally productive).  You might file or search; you might believe in an empty Inbox or not; you might leave your email on all day or disconnect your email program for part of the day.

(I happen to be: search not file; no empty inbox; on all day.  You?)

The big question is, what exactly do you DO when you open up your Inbox?

The FIFO philosophy (first-in, first-out) has you digging from the back…you start with your oldest email and work backwards.  I suspect this is an uncommon strategy for all but the most avid empty-inboxers.

LIFO (last-in, first-out), conversely, has you start with whatever came in most recently.  It’s tempting and rewarding and, I suspect, a terrible strategy most of the time – instant gratification disguising itself as productivity.

I’d propose a NIFO strategy instead: none-in, first out.  That is, you open your email because you have something specific to get done, someone you want to reach out to, a very important action that you want to initiate.

Since you have many very important things to do (customers to call on, projects that you are moving forward, etc.), starting with these, rather than starting with replying to whatever everyone else wants you to do, allows you to own your agenda rather than have your agenda own you; it ensures that when you run out of “email time” (as you inevitably will) that the things that are left off the list aren’t the five most important things you have to do; and if you’re disciplined about this you’ll never dive into email just to empty your inbox…you’ll start with actions you want to initiate and then (and only then) will get to “replying all.”

Shorten your backswing

It was time today to sit down and write a blog post.

I keep track, by email, of blog post ideas when they happen, and was just about to go into that email account when I saw an interesting tweet….that led me to a clever article about Occupy Wall Street, that….  wait a minute, what was I planning to do?

There’s the real work we need to do, and there’s all the muss and fuss that we do as part of our process of starting our real work.

This can happen a lot in sports.  In racquet sports there was a whole move-my-racquet-forward-before-hitting-a-backhand thing that I used to do.  I have the same problem (never fixed) when throwing a frisbee.  If you ever go to a yoga class, watch how much hair-fixing and water drinking happens at the exact moment the instructor calls out a challenging pose.

It feels minor, but think about all the wasted motion I was doing for the 500 backhands I hit in a one hour squash game – energy spent, speed reduced, extra steps taken for absolutely no reason other than that I’d built up a bad habit.

This isn’t just about not getting distracted by social media and your inbox (though those are particularly dangerous because they pretend to be work).  It’s about shortening the distance between “I’m going to start working” and “I’m working.”

Time to be a little pushier

A friend of mine who’s a media executive described a recent meeting thus:

“At the end of the meeting, their CEO agrees we’ll have a decision by Friday. Then she said, ‘…and you may need to bug me a lot before then, send me a lot of emails on Thursday, call me…go ahead and do it, I won’t mind and I’ll probably need to be reminded.”


My friend’s take on this well-intentioned statement was that we’ve gotten to such a level of media (email, web, social media, etc.) overload that senior folks in all walks of life are simply abdicating responsibility for being functioning, capable people who stick to deadlines, reply in a timely manner, remember what they say and follow through on their promises.

It’s a sad state of affairs which basically says: I leave it up to you to bug me enough that I pay attention.

There are lots of directions we could go from here – about people not spending time on the right things; about how more information is leading to less effective leadership; about fighting this tooth and nail in your organization by creating cultural norms that are the exact opposite of this tidal wave of abdication of responsibility.

Instead, let’s be overwhelmingly practical and take this moment to remind ourselves that the ability to stand in front of a person and get their real attention is more at a premium than ever.

That you need to master multiple channels of communication to get through to different folks (texting in Europe and the developing world; email plus phone plus text here in the U.S.; etc.).

That, instead of sending the eleventh email and waiting, you’d best have your top customers/clients/relationships on speed dial. (Really.  Do you?  Do you have the cellphone number of all your Board members in your phone and at your fingertips?  Why not?)

On the margin – sadly – I bet you have to be a little pushier than you’d like to be in order to break through.

Spam tax

Somehow the spam I’m getting is getting better with subject lines that make me open the message (hmmm, maybe they’re reading some of my posts!). Things like “Can we meet this week?” and “Following up about next week’s lunch.”

I’m a huge, huge fan of Chris Anderson’s email charter and believe that there’s a LOT we can do to free ourselves from the non-spam email onslaught by changing our own behaviors and expectations.

But spam is still a huge amount of all email sent (as much as 90% in 2009, though it has been dropping lately), and spam that’s getting through my (and your) email filter is getting smarter every day.

So here’s an idea: create a $0.10 spam tax that is platform-independent (works on Google as well as Outlook).  If an email recipient hits the “report spam” button:

  • They are automatically unsubscribed from that email list (this may be difficult to implement, but if possible it would prevent abuse of the “tax them” link while also killing two birds with one stone – unsubscribing + tax)
  • If more than a certain number of people (100) qualify an email as spam, the tax kicks in (again to prevent frivolity)
  • Implement this universally with a single searchable web-based database of spammers, also listed tax paid, etc.

There’s some work to be done to make the tax big enough to have this be a real deterrent – ideally the tax level would be greater than what spammers pay to buy my email address.

This feels like a pipe dream, but maybe someone can take the idea and make it better.

My Outlook “Block sender” button doesn’t feel like enough any more, since these people are actively cutting into my (and your) productive time, and it would be of great public value to architect a “sin tax” that puts a damper on this.

For the comments section: what would you do with the money collected through this tax?

It’s not personal (and that’s the problem)

OK, I know you’re busy, we all are.

And you have a lot of people you want to connect with.  We all do.

And yes, it’s true, sometimes you copy and paste stuff into more than one email, because the meat of the update might be pretty similar from person to person, right?

But here’s the decision you get to make: how much value do you place on making the person on the other end feel like the note was written just for them, every time?

Outlook has a whiz-bang feature that allows you to create a text email that is, in fact, a mass mailing.  It’s tempting isn’t it?  Think how efficient it would be!!


Except you have to decide if relationship-building is a mass-market undertaking.  You have to decide if scale comes from going broad or going deep.  You have to decide which tradeoff you’re willing to make, because halfway there is no man’s land.

Sure, you’ll be careful most of the time.  But the moment a giant block of text in your email is in another color, or another font, or another size, the illusion is shattered. The moment you email the same thank you note to five different people, the wires appear to the whole audience, and the magic of your flying act goes *poof*.

And the thing is, the moment someone discovers that they’re the kind of person who gets impersonal notes from you…well, there’s really no way to recover from that.


Re: Question

Never let an email go out of your inbox with this subject line.  Instead, answer the question in the subject line.

Why?  Why bother being persnickety about such a trivial thing?

Maybe it’s not so trivial.  The subject line is of each email you send is your headline.  Can you imagine if the NY Post’s headline today had been “Re: IMF”  (instead of “French Whine” in reference to Dominique Strauss-Kahn not being given any special treatment by the NYPD.)  Re:IMF doesn’t sell newspapers, and it doesn’t help your email get to the top of the pile.

The subject of your email is a trigger for people to read your note (or not), to read it immediately (or not).  Tweaking this is one more way to avoid letting your message get lost in the shuffle.

A guy I know puts my name in the subject line of every email he sends to me.  It’s pretty weird, pretty far outside of regular email norms, but I absolutely know when an email is just to me and when it’s to a group, and it makes a difference in how I respond.

So, for kicks, a list of norm-breaking email suggestions:

  1. If you are the author of an email, make the subject Tweetable.  (NOT “Question” but instead “Should we move the launch date up a week?”).  Flex those 140-character-or-less authoring muscles for something more useful.
  2. Have as few people as possible receive every email
  3. Especially when you ignore #2, establish that you want replies from people in the To: line.  Cc: means “I’m just letting you know.”
  4. If someone has written a vague, general email subject line, change it.  Reply to “Question” with “Moving up launch date [Re: Question]”  This way the email is still searchable under the original subject plus it’s more clear to everyone what’s going on
  5. When an email thread veers off to a totally different topic, start a new thread or change the subject line.  Having a conversation about a potential promotion in a thread whose subject is “Re:Staff Retreat” is just plain inefficient.
  6. If threads are getting really long, pick up the phone instead (yes, that counts as an email tip)
  7. If a conversation has become irrelevant to some people, drop them off
  8. If #7 makes you/them uncomfortable, move the people who are being dropped off to Bcc: and say in the note: “I’m moving Pankaj and Sarah to Bcc: and the rest of us will continue the thread.”
  9. Make your emails shorter
  10. Write each email as if the time of each of the person reading it is valuable – because it is, even if being loose with these sorts of things feels like a hassle to you.

I wish all the popular email programs made it a default to have the cursor jump to the subject line when you hit “Reply.”  In the meantime, my answer to “Re: Question” is “No!”

One thing

Most of the time when you send an email, that’s how many things you can get someone to do – if you’re lucky – so that’s all you should ask for.

One things are:

  • Watch this video
  • Read the attachment
  • Come to this event
  • Can you answer this question?
  • Can we meet?
  • Thank you

One things aren’t:

  • Can you give me some advice and can we meet?
  • Here’s an update and also would you read the attached
  • Thank you and could you do this other thing?

When you ask for two things, at best you’ll get one of them, and there’s the risk (thank you + would you please…) that by combining two you end up with none.

Tweet your subject line

Remember memos? They used to be sent around in manila interoffice envelopes, a list of names crossed off on the outside.  Memos presaged their digital doppelganger, email, with “To:, Cc:, Date:, and Re:” laid out in black and white.

Difference is, you used to get a few memos a day, and when you’d scan a memo, you’d see the whole thing.  So the subject line (“Re: Project status update”) wasn’t important.

Now people are receiving and scanning tens, maybe hundreds, of emails a day, and they are figuring out how to triage and prioritize them based on three fields: who sent the email, the date/time, and the subject line. Since you can’t change your name or what time you sent the email, the subject line has become the most important part of what you’re sending. 

So avoid generic subject lines and summarize the email instead. Create a 140 character Tweet of your email. Be the opposite of generic.


Not “Project update.”   Instead, “We’re on track for Friday’s deadline”

Not “Hope you’ll join us!”  Instead, “Hope we’ll see you Monday at 6pm – tickets running out”

Not “Re: Our meeting.”  Instead, “Sorry I have to cancel tomorrow’s meeting [Re: Our meeting]”

This may work better internally than externally, since externally you may not want to stand out in this way (or maybe you do).  But I bet 80% of the email you send is to your 10 closest contacts anyhow.

Tweet your subject line to help them (and you!) figure out why you’re writing.

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Nothing magical happens when my Inbox is empty.

There’s no pot of gold at the end of that rainbow.

Which means I can decide whether or not to care about this.

And so can you.

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Reorienting Haiku

Unread email piles

It can only mean one thing

I’m getting more done

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