Microsoft Outlook changes emailMicrosoft’s new mail service may finally drive some much-needed innovation in email. (Disclosure: I have Microsoft stock from my time as an employee there.)

Box CEO Aaron Levie tweeted, “Someone has apparently slipped an innovation drug into Microsoft’s water supply recently. This is getting interesting.”

I agree. This is definitely one of the more innovative products from Microsoft. It’s clean, it’s simple, and it’s easy to use.

The last fundamental innovation in email was in 2004 when Gmail launched. I’ve been a Gmail user ever since.

But despite huge increases in the volume of email we deal with in the last eight years, little has been done to improve the core experience. Yes, Google launched Priority Inbox. It’s supposed to help you figure out the important mail; for me, it’s been largely useless. Scanning through my inbox, very little of what Google has marked important really is.

Google’s other major moves with Gmail have largely been about trying to exploit its huge number of mail users into whatever lame social product Google is trying to bootstrap. (Remember Buzz?)

But better email tools could improve productivity for everyone.┬áIn the current version of Outlook mail, there isn’t enough innovation to get me to switch. But the existence of a new and credible player who wants to win may drive much-needed innovation in email. Here are some core things that would get me to switch by delivering value, not by tricking people like Facebook tried to do:

Automatic classification

Outlook’s “Quick views” feature offers a quick view of how that could happen: automatic classification of mail. The system automatically scans email for certain attributes that people look for. Oh, hey, this email looks like a shipping confirmation. And this one has a photo. And these have attachments.

That’s pretty rudimentary. But imagine that your email tool could do this:

  • Separate receipts from marketing emails. I have eight years’ worth of emails from Amazon,, Groupon, etc. Sometimes I want to look up what I purchased, or I need warranty service. Finding those receipts can be a challenge.
  • Pluck out bills. Emails from American Express could be scanned for payment due date, and the date could automatically be added to my Google Calendar.
  • Keep my travel top of mind. Itineraries, hotel confirmations, and rental car reservations that are upcoming would be available in a dashboard view.
  • Identify emails with expiring content. Nordstrom’s anniversary sale ends August 5th. This could be put into a Quick view that becomes more prominent when the date approaches and drops out when the sale ends. Expired emails would also be downweighted in search results.

Some of the above can be done with search. For example, I can search “ receipt”. But look what happens when I do that:

I get a bunch of unrelated junk. What you can’t see is that the list isn’t complete. I’ve purchased much more from In order to get all of my receipts, I have to search for “ thanks for your order”.

Another way to tackle the problem is filters. I have set up numerous filters that file things like receipts, daily deal emails and the like. (You can see some of my filters in the screenshot above.) But that’s a real pain to set up and only geeks will do it.

There are vertical players that are focused on solving pieces of the problem. TripIt and Kayak will parse travel-related emails. I forward my confirmation emails to TripIt, it picks out the relevant details and creates a more consistent itinerary. It can even generate a feed of events that I plug into Google Calendar. That’s a really roundabout way of doing things. OneReceipt and Slice do this for shopping emails.

But the separate apps have little traction. It should be built into the email platform. And once it’s in a large scale system like Gmail or Outlook, emailers will have an incentive to markup the information they send to make it even more actionable.

Google has built a very lucrative business on organizing the world’s information. It should do a much better job of organizing my information.

Secure email

It’s somewhat mind boggling that this far into email adoption, unsecure email is standard operating practice. Yes, there have been some improvements. Gmail uses SSL for your mailbox. That wasn’t always the case.

But if you actually send something, that email is sent unencrypted to the recipient.

Securing email has had three historical challenges: it needs to be easy for the user, it needs to be universal, and it needs to have a business model.

Early experiments like PGP, which put a lot of work on both the sender and recipient, have failed in the consumer market. But for person-to-person messaging, we’re down to a small handful of providers that matter. (Yahoo, Google and Microsoft.) Among them, they should be able to solve this problem, at least for email sent among their networks.

Secure email is also something that would help with financial transactions and could potentially cut the flood of bills that are sent via paper mail. That the post office is running ads touting that paper mail is more secure than email is ridiculous. Not because they’re wrong, but because it’s true.

Even among my more tech savvy friends, many receive paper bills because the process of getting their bill or statement from each credit card company is difficult. If you have multiple accounts, it’s even more complicated because each financial institution has its own system. There is no interface as consistent as ripping open an envelope. They also have different rules about how long they keep old statements online. All of this stuff should show up in my email box as effortlessly and more securely than it does in my regular mailbox.

Because email recipients are concentrated on a few networks, it would be possible to have direct secure transmission of these statements and account notices. Doing that would also reduce the scourge of phishing, because the mail provider could authenticate that an email came from American Express or Bank of America.

This is a service that banks should be willing to pay for, both because it reduces their operational costs (mailing and printing statements) and because it reduces fraud liabilities (phishing.) Even at 5 cents per secure communication, it’d be a bargain.

Not only does this increase productivity, it’s better for the environment. The people who lose out are postal workers, especially the guy who’s job it is to convince banks that they should use paper statements instead of email. (I’m not making that up. Talk about a Sisyphean task.)

Will any of this happen? A guy can hope. And there’s nothing like real competition to help drive it.

If someone is willing to add these features, I will jump ship from Gmail. I would even go back to my Yahoo mail account.