A Lot Has Changed In A Century, But Not Everything

Randall Stross’ Digital Domain column in the NY Times is one of my favorite regular features of the Times. This week he tackles an issue near and dear to my heart: email overload.

For a brief period last year, I was the poster boy of email bankruptcy because the media picked up on this post and it percolated for a month or two, including landing in my parents home town paper. They got a chuckle out of seeing my name in their daily read.

Fortunately, the poster boys (at least for Randall) are now Mike Arrington and Mark Cuban. Based on the numbers that Randall cites for Mike and Mark’s incoming email, I can say that I do feel their pain, literally. I get that kind of volume too.

And let me tell you, there is only one workable solution that I’ve ever heard to deal with 1000 incoming emails a day that all want a reply. It’s turning your inbox over to an assistant or a group of assistants as Randall points out that Thomas Edison did:

This was the solution  Thomas Edison
used in pre-electronic times to handle a mismatch between 100,000-plus
unsolicited letters and a single human addressee. Not all
correspondents would receive a reply — a number were filed in what
Edison called his “nut file.” But most did get a written letter from
Edison’s office, prepared by men who were full-time secretaries. They
became skilled in creating the impression that Edison had taken a
personal interest in whatever topic had prompted the correspondent to

I am not going to do that. I believe that if people wanted a note from my super nice assistant, they would send her the email not me.

I do forward many of the emails that come to me with new investment opportunities to Andrew who does a way better job than I do at replying to all of them. But even then, I don’t always get to every email so not everyone gets to Andrew.

Randall talks quite a bit about HL Mencken who apparently answered every letter he received on the day he received it. I think a lot has changed in the century (or at least the half century) since HL was doing that.

First, the letters he was responding to were written once and sent. There was no write once, send many technology working it’s nasty effects on his inbox back then.

And the time delay between sending and recieving letters meant that letter writing was saved for things that were not urgent. We have the opposite effect at work now. Urgent emails are missed because of all the email that is not urgent and may not even be relevant.

And of course, I don’t do email with a cigar in my mouth. Maybe I should.

But there is one thing that Menken said that rings true to me and may be the source of my email anxiety.

“If I write to a man on any proper business and he fails to answer me at once, I set him down as a boor and an ass.”

I am sure that every day people are setting me down as a boor and an ass and that’s a problem. Without a solution as far as I can see.

#VC & Technology

Comments (Archived):

  1. John Underwood

    Have email systems done enough to facilitate quick responses? For example, what if you could customize a number of one-click responses? If I’m a sender, I’d rather get a quick semi-automated response than nothing at all (and I assume the status quo results in nothing at all for some portion of emails).

    1. fredwilson

      I think you can write scripts and there are smart keys and things like that but power users are a small percentage of total users and nobody focuses on themFred

      1. daryn

        In addition, most people writing to you probably aren’t looking for the form-letter response. While I suppose an acknowledgment of receipt is nice, it may actually be worse if it allows you to spend even less time paying attention to the contents of the message.Templates and 1-click responses are great for things like tech support, and there are tons of solutions, but as you alluded to with your comment about your assistant; in this case people want to hear from the real you, not get an auto-reply or a hand-off. That said, if I sent you a pitch and Andrew replied, I’d still be pretty happy :)It’s a tough problem; there are plenty of optimizations that can be made, but I’m not sure there is a solution.

  2. Erik Peterson

    Is there a business here? A company that employed a set of intelligent, well-spoken “secretaries” who thoughtfully respond to email all day long could get a lot of business, I think. Why not outsource correspondence?

      1. Erik Peterson

        No, actually. But I think I might.

    1. fredwilson

      Because correspondence is personal. All business is built on relationships not robotsFred

      1. D. C. Toedt

        I’d be interested in the context of the Mencken comment you quoted. Out of context, it makes the Sage of Baltimore look like a bit of a boor and ass himself. When a man professes to be entitled to claim the time and attention of anyone he chooses merely upon his demand, many would label him an egomaniac.

        1. daryn

          D.C. – As a Baltimore boy who has read his share of Mencken, the egomaniac label isn’t entirely out of place.. However, it is an interesting observation.I don’t think that all of the people contacting Fred and Mike are egomaniacs, but because interaction through comments is such an important part of their blogs, the reader feels that this should also extend to their email. If this blog was written by “AVC Staff,” perhaps it would be different; far less engaging at the blog-level for sure, but also far more detatched. The same goes for TechCrunch. Even though there are now multiple authors, they each post under their own name, and readers get a feeling for each of their personalities and with whom they can relate.While I wouldn’t consider Fred or Mike or Erick a boor or an ass for not responding, it would certainly bother me more than not getting a reply from say Tim Draper or Walt Mossberg.

          1. fredwilson

            Relationships, no matter how tenuos they are, require investment

          2. D. C. Toedt

            We may be talking apples and oranges here.Yes, even tenuous relationships require investment.No, a stranger — the extreme case being a spammer — isn’t entitled to proclaim a relationship and demand a corresponding investment of your time.

      2. Erik Peterson

        Well, it would be real people responding individually to the emails, but it wouldn’t be the person who they actually wrote to.This kind of thing used to be really common with celebrities and snail mail letters, but it seems like it hasn’t really made the jump to email. It seems like that kind of model would be much more scalable with email.

      3. Taylor Davidson

        And that’s the problem: we use and think of tools like email as “correspondance”, but the tools we use mean far less than they used to. The massly reduced effort to send and receive communications to one person, to say nothing of the ability to instantly add masses of people, means we are not corresponding with the same meaning we used to. Websites, email, blog comments et. al. are like the public signs, billboards and bulletin boards of the past, communication methods that lack social relationship context and thus were not intended to be used for one-to-one communications.Yet we cling to the notion that email are more like personal letters, which leads to the social guilt over not responding.Cultural shifts lag technological shifts.

  3. ivanpope

    I think there is a long tail of email overload. There won’t be that many people in the head of it, most of us are in the tail, i.e. our overload comes nowhere near the scale of Arrington or Fred. They have a professional and chosen interest in high exposure and lots of attention, so they get too much email. Myself – I get enough, but it’s manageable I think. So how many people in the head of email overload and how many in the long tail?

  4. harpos_blues

    Fred,If you are using you Mac for e-mail, here are a couple of tools, one is native to OS X (and fully programmable, even for non-developers), and the other is an inexpensive third-party application.From OS X: Automator – It’s in your applications folder. Automator creates work flows for repetitive tasks, and takes full advantage of the drag and drop interface. You can create individual components (tasks) that can be combined into a workflow (job). Workflows can also be linked together.As you are an inveterate dabbler, you may enjoy this tool. There are also many online sources for downloadable Automator actions, including Apple.Third-party applications: MailTags and Mail Act-on: http://www.indev.ca/MailTag… and http://www.indev.ca/MailAct… Both of these tools are huge productivity boosters.Hope this helps

  5. preetam

    Maybe there isn’t a solution, but I think patience and perseverance plays a hand in this equation as well- it’s not just about how many emails you cannot reply to…it’s also about how many folks empathize with your not being able to reply and patiently wait their turn and give it a shot again(and with some degree of sophistication, so as to not get achieve a SPAMMER label).The scarcity is your time- the value is your attention. I’m not sure you can compromise on your value, in order to achieve efficiencies that mitigate the scarcity.What might be useful is if there was an engine where you could plug in the number of hours you’re able to spend on e-mail on any given day, and accordingly, it parses your e-mails based on certain rules(you know….investment prospects = 10%, financing follow-throughs = 25%, personal = 5%, et al.). The rules could be dynamic too- you could have more “personal” time on a saturday, than on a monday, for instance..If the engine had a learning agent built in, it could also start making assessments on how those %ages even out over time, and reduce your efforts in having to allocate the time/day, %age attention/day, every day.Of course, the biggest challenge would be the actual filtration of e-mail content- but there’s lot of b-network theorists/heuristic gurus out there…should be a walk in the park for most to pull that off… 😉

  6. falicon

    It’s not ideal, but one suggestion for those that get massive amounts of email would be to impose some rules on the people who send you email…Basically say something like “if you want to talk to me about investments, then your subject must contain the word investment in it somewhere”…”if you want to tell me something personal, then your subject must contain the word personal in it somewhere”…etc. etc.Then you can set up a script that auto-responds to any email that doesn’t fit into one of your rules (sharing the rules with them and letting them know that the current email *may* not be read for some time as it’s not ‘classified’)…and then of course you can just set up filters to dump the various messages into the proper folders for you…While it doesn’t really solve the problem of answering everything…it would at least give you a chance to pick which topics you want to spend the most time responding too…and it gives the rest of the random emailers some rules to follow if they really have something important to share with you and if nothing else, a notice that it could be some time before they get a response from their random email (if ever)…

    1. Ennis Al-Asaaed

      You’re right of course. There is so much attention on smart heuristic filters where as a simple solution works much better. Companies using phone systems have already dealt with this issue and have a fairly manageable way of dealing with a large number of calls. The onus is on the customer to direct their own call to the right person first. There is nothing wrong with that. I’m an Engineering student. If I wanted to get Fred’s input on an idea of mine I’d be willing to make sure my email gets put in the right folder.The quickest answer isnt always in better technology. Sometimes we can change our behaviour to do away with issues that annoy the crap out of us :p

  7. Guest

    With regards to this point: “We have the opposite effect at work now. Urgent emails are missed because of all the email that is not urgent and may not even be relevant.” – About 2.5 years ago I moved to London and I realised (yeah, I’ve been here long enough that I’ve started spelling like a Brit) something about a year back. I’ve made a lot of new friends here and I have almost none of their email addresses. Their (and increasingly my) preferred method of communication is the phone, specifically SMS. And if not SMS, then Facebook. And we seem to tier messages based on priority: SMS for something that requires an urgent response and a FB message for things that don’t. Now, this is exclusively within my London social network (Europeans / Brits in their 20s and early 30s) and it has yet to cross-over into my “work social network”. But I also think there is a generation of people who are going to be entering the workforce in the next few years who have become accustomed to communicating almost exclusively through social networks/IM/SMS, so I have trouble imagining email is going to remain the de facto method of reaching someone. Particularly as information / communication overload continues to grow as a problem.

  8. WayneMulligan

    There’s a big opportunity here if someone could do it “right”…not to jump on the “social graph” bandwagon, but what if we could use our social graphs to help prioritize email. For instance, if someone created an email client (better yet, an add-in for existing clients) that would give you a way to sort mail based on how “connected” you are to a person. Could be a point based system and it would use criteria like:1. Email history (e.g. have you corresponded with this person before, how long ago, how many times, etc.)2. Connect to your Facebook or LinkedIn profile and assign points by how well connected the person is to you (degrees of separation + number of mutual connections)3. See how engaged the person has been with your digital presence (have they commented on your blog posts – could pull the data from disqus – or your flickr photos, or sent you a tweet on twitter, etc.)I’m sure there are some other relevant data points here but the main idea is that getting through 1000 emails a day is always going to be tough no matter what. But there are some emails that really can wait and there are some emails that deserve a quicker read and reply. How we organize those emails is what will ultimately determine which ones will get read and replied to quicker.Anybody have any thoughts on this or know of an add-in that does it already? Might actually be fun to go out and just build it if it doesn’t exist.-Wayne

  9. qwang

    Besides direct communication, email is kind of a catch-all for all other categories of communication. My in boxes is filled with reply-alls about where to get dinner friday night–a conversation that could be moved to Twitter, announcements and mailing lists–that could be auto-prioritized, “utility” emails such as social network notifications or credit card balances–which really belong in in a separate “services feed”. We need to start getting smart about categorizing indirect-communication into tiers that are easily prioritized.Besides smarter technology, we *also* need a little culture change:1 – That it’s ok not to reply to all emails, especially ones that are unsolicited or don’t get to the point quickly enough2 – That we should think harder about what is the best communication channel for each message — should I send a fbook message? leave a blog comment? a twitter @reply? post on a discussion forum whom my target frequents?At the end of the day, we are consuming more information faster than ever. Technology has made us far more productive and thus feel much busier…nothing wrong with that as long as you choose to lead this life =)

  10. terrycojones

    Hi Fred> I am sure that every day people are setting me down as a boor and an ass and that’s a problem.> Without a solution as far as I can see.I don’t think this is right. There’s no solution if you think the solution involves you replying to all mails or blog comments etc. Email is *different* and people know it’s different. The solution is for that change (the realization that email is different) to continue. Even my parents understand that the dynamics of email answering are different, and young people certainly do. BTW, my email setup is hacked left, right & center. See http://www.fluidinfo.com/te… and http://www.fluidinfo.com/te…In the meantime, you have the advantage of being in an industry where people expect boors and asses :-)Terry

    1. terrycojones

      I just woke up realizing why I believe what I wrote above. Email is stuck between the old world and the new world. The old world was dominated by synchronous communication patterns: rigid, slower, more rules, more structured, etc. The new world will be dominated by asynchronous ones, such as SMS, Twitter, and blog comments. Email is obviously an asynchronous method, and computational advances have made it possible for us to send tons of emails (no need to buy paper, envelopes, stamps, or to write slowly, or to go to the post office). But the related and necessary change of expectation is slow as we still have one foot in the past (it’s “mail” like “postal mail”, right?). I’m sure the solution does not lie in heading back towards the slow old synchronous model. It’s not about becoming impolite, it’s about becoming faster. Expectations and perceptions will change as to what’s impolite, as they are. Sure, some asynchronous comms go unanswered, as on Twitter, as in blog posts (like my last comment, sadly ignored these past 7 hours), but everyone knows that’s the norm. An older generation may have to die off before we lose the feeling of guilt, legacy of a more synchronous form of “mail” and its expectations.

      1. falicon

        I agree that we – as a collective group – are currently stuck in between the gaps of another revolution. This time we are going from physical ‘things’ to digital ‘things’…many non-digital people still crave things like cds, while younger digital age people tend to crave mp3s instead…I find myself craving both (to fit all my needs in the gap – for example I still prefer cds for the car)…I think of this as a revolution like that of the industrial revolution because it’s changing more than just a vertical or two (like the music industry)…it’s seeping into every aspect of every day life…including the very means we use to communicate and learn…the struggle with things like email are the ripples of the revolution that only those of us in the gap will ever feel…but experiencing those ripples is part of what makes living through this transition time so exciting and fun – at least for me!

      2. fredwilson

        terry – i like this comment and reblogged a small part of it on fredwilson.vc

        1. paulsweeney

          check out http://www.bioteams.com for some articles and studies on how one way communications (i.e. sms – twitter streams) are more like how ants communicate, and are effective for some good reasons. I also think that one of the challenges is finding out when asynchronous should switch modes, i.e. when an action bias takes precedence over a communications flow.

          1. gregory

            not only ants.. intuition is one way, often very reliable… even more woo woo, faith and trust, the confidence to know that you are getting what you need when you need it, seems to work like gravity to bring the needed stuff to the mind on time

      3. fredwilson

        TerryI don’t want to wait ’till to die to become guilt freeFred

  11. jackson

    Two words: auto reply

  12. Steven Kane

    I know I risk being banishment but — maybe its time to assess fees for email, like postage stamps. $0.01 per send?will immediately reduce email trafficand will also immediately generate big funds — which maybe can be mandated to go to gov’t R&D fund for alterantive energy tech or other good works that the online community in theory would happily support

    1. fredwilson

      Banishment from where? This blog? Never!

  13. Helmar Rudolph

    The problem with email is that despite some eye candy on the client side, the underlying architecture is still the same as it was in the 70s or 80s. I have proposed to many an email client developer (Opera, Becky, The Bat, etc.) to create an optional flag called NRN – no reply necessary, plus the necessary X- flag in the mail header. Then you know right away that the sender doesn’t really need a reply. Better still, you can have an optional selector that allows you to set a “reply within x hours/days/weeks”, once again allowing the recipient to manage that mail, rather than just storing it and requiring you – the human – to figure out how to treat that piece of correspondence.So, once again, the underlying architecture is outdated, and the mail clients are simply mail storage applications, but not mail MANGEMENT applications. Why? Coz they’ve been written by techies without sufficient or relevant contact to those who are actually using email on that scale as you and I do, Fred.Time for a change. Who’ll be the first to come up with a mail management application instead of another eye-candied storage app?Helmar