It’s been a busy year for Javier Soltero. First, in a move that transformed Microsoft's lagging mobile email strategy, Acompli, the mobile email startup he led as CEO, was acquired by Microsoft in November 2014. Now he finds himself as a corporate Vice President charged with taking the entire Outlook business unit (and all the various Outlook clients) into the future. Given that he has come in as an outsider to a product family that's been around for nearly twenty years, Javier seemed like an interesting person to chat with, which is just what I did recently.

First, a declaration of intent. I have used desktop Outlook since its introduction in 1997. Like many people, I use Outlook (2016) for hours daily, so it’s an essential business tool for me. On the road, I use the universal Outlook app in Windows Mobile 10 running on a recently acquired Lumia 950 XL. And I use Outlook Web App (OWA) too when needs must, such as over bandwidth-constrained connections. You could say that I like Outlook.

A streamlined version of Outlook desktop

We began by discussing the desktop version of Outlook. I expressed my opinion that Microsoft hasn’t made a significant technical breakthrough with the client since Outlook 2003. That version introduced drizzle-mode synchronization and a pile of network smarts to enable a user to have a complete offline copy of their mailbox and work while being insulated from network glitches. Although important when introduced, that capability is even more so now in the era of cloud services when network connectivity across the Internet to Exchange Online isn’t always brilliant. Subsequent innovations, like the recent change to use MAPI over HTTP as the default connectivity protocol, are worthy but have not changed the way people work.

Javier agreed, but observed that the massive size of Outlook’s installed base makes it tough to make “bold moves”. He said that Outlook has now become “too complex” and cited the compose screen (Figure 1) as an example. There’s lots of functionality available that serves a segment of the user population very well because they’ve invested the time to master all the features. Outlook is also very customizable and that makes the client difficult to support – and difficult to carry those customizations forward to new versions.

Javier stated that Outlook wins when it makes email better. He said that his team is in the middle of reviewing every feature in the current client to ask the question whether the feature does make email better. He pointed to the implementation of “likes” and “mentions” in the Outlook clients as examples of changes that he thinks are helpful. As I have noted before, I don’t really see much goodness in “likes” but am more positive about “mentions”. I guess it helps Outlook seem a little more modern, but would prefer if engineering effort was dedicated elsewhere to make the clients a little more manageable.

I think the "events from email" feature announced on December 18 is an example of something that makes email better. It's actually surprising that no one at Microsoft ever thought of automatic extraction of flight information from email confirmations before (Gmail has had the ability to automatically recognize and create events since 2014). The processing to analyze flight information occurs on the server so all clients are supported. Two other points are that work is required to recognize information from email, so not all airline confirmations are supported (like any non-US airline). Also, this is an Office 365 feature and there's no mention that the feature will come to an on-premises server.

Returning to Outlook, the outcome of the feature review is likely to result in simplified and streamlined versions of Outlook in the future. Javier wants to find the “soul of Outlook – whatever that is” and make it better. People like the combination of email, calendar, contacts, and tasks and that won’t go away, but things will be done smarter with more intelligence built in to make it easier for users to work with email.

What really matters to users

Javier figures that his experience of developing software, including the successful Acompli (now Outlook for iOS and Android) clients, has given him a good sense of “what really matters” and is prepared to lead with conviction in changing things to make the product better. He acknowledges that any change will result in mixed feedback; some will love changes while others will loathe them. It’s just part of the scenery when you attempt to improve a product that’s used by so many people.

Even so, Javier reckons that because he is a relative outsider with no history with desktop Outlook, he can act as an agent of change and bring the client forward by focusing on what really matters in terms of making Outlook different. And he wants to do it in a way that people view Outlook as much the same thing no matter what client variants they use. And that includes the Outlook for Mac client, something that will come as blessed relief for the long-suffering fans of this version.

It will be interesting to see if Microsoft can bring the current Outlook 2016 client forward so that new versions are both simplified and more functional. At first glance, it seems like simplifying matters while adding intelligence and functionality are mutually exclusive goals, but given that Outlook has been around for almost twenty years, it seems like a good idea to ask some fundamental questions about how people use and like the client (and why some hate it) and whether the package of features that surround the core email functionality are all required or could be improved.  

Mobile Outlook

Moving to mobile clients, we chatted about the progress that has been made since the Acompli apps were rebranded and launched as Outlook for iOS and Android in January 2015. The early days saw some tough going as many commentators focused on deficiencies (some perceived, some real) that needed to be addressed before the apps could be used in the enterprise.

Well, since then, the Outlook apps have been in a constant state of development and have clocked up some 30 million installations. As Javier noted, the apps are not included in any operating system so every download and installation marks a deliberate decision on the part of someone to use Outlook as their email client. It’s a real testament to the Outlook brand as well as the user experience that the clients deliver. People have voted “with their thumbs” and Microsoft has responded by bringing the apps along a rapid update path to react to customer demands.

Javier noted that it has been a balancing act in development to respond to demands for features that are important for large enterprises while not losing sight of why people want to use the apps. For example, support for multi-factor authentication is important to comply with corporate security policies, but it can’t be implemented in such a way that the feature interferes with client usability. Javier said that Microsoft wanted to make sure that the Outlook apps deliver functionality to delight users and cited the integration with the Sunrise calendar app (acquired in February 2015 as an example.

The biggest remaining hurdle from all the complaints leveled at the Outlook mobile apps is their continuing dependency on Amazon Web Services. Data downloaded from user mailboxes is processed in a repository hosted on AWS in the U.S. in order to create the “focused inbox” (Figure 2), the most distinct element in the user interface of the Outlook apps. The natural question arises as to why it’s taking so long to move this processing to the Office 365/Azure platform and preferably one that accommodates the need to respect customer wishes for the location of data at rest in various countries.

Javier acknowledged that using a non-Microsoft platform remains an open issue and said that work is progressing to make sure that the transition happens in early 2016. 

It’s also true that Microsoft still has some work to do to upgrade the functionality of the Outlook apps before they can retire the now-obsolete but still available OWA for Devices apps, which are still available for iOS and (in preview) for Android. OWA for Devices runs Outlook Web App inside a browser container and as such is able to deliver all of the functionality available to OWA, such as being able to access shared mailboxes. However, the client is slow and doesn’t work as well as a native app.

In the Office 365 Network, another Microsoft representative indicated that OWA for Devices would be left "as is" until after the Outlook apps had transitioned to the Office 365/Azure platform. However, Javier would not confirm when OWA for Devices will be retired, which is probably natural given the amount of functionality that has to be moved over to the newer Outlook apps.

Universal Outlook

Thoughts turned to the universal Outlook app, now available as the "Mail and Calendar app" in Windows 10 and Windows 10 Mobile (Figure 3). I expressed the view that the new client wasn’t very exciting and no great advance over what was available before in Windows Phone 8.1. As evidence, I pointed out some problems with email synchronization where new mail was not delivered to the phone even when it was configured to deliver new items as they arrive. I cited an example where I had noticed that no email had arrived in 35 minutes (unusual for me in mid-day) only for ten or so to arrive after I forced synchronization.

Javier admitted that some synchronization problems exist in the universal app. On the surface, this seems strange because the client uses Exchange ActiveSync, a protocol that has been used for over ten years. He noted that the universal app had been written from scratch and that a big update was due soon that would fix many synchronization glitches.

In fact, the Outlook team is pushing out weekly updates in an aggressive plan to improve the fit-and-finish of the universal app. The latest update includes the ability to "undo" a delete operation as well as other fixes. Updates can be installed automatically on Windows 10 Mobile devices, so if you use this O/S, you might have the software now. If not, click the Store app and select Downloads and Updates to get the latest version.

On being a phone creeper (but in a nice way)

Javier admits to being a “phone creeper”, which sounds a little weird but is really just evidence of his natural curiosity to know whether people use Outlook on their mobile devices. So if you see someone taking an unnatural interest in how you process email on a smartphone, it might just be him doing some personal market research! The natural question that flows from his inquisitiveness is whether he looks at other email clients like Google’s Inbox or even Slack to learn from them. Javier’s view is that all clients have something that they do well but he’d prefer to concentrate on improving the Outlook clients rather than mimicking features drawn from elsewhere.

Turning to the Outlook family as a whole, Javier is encouraging the developers of the different Outlook clients to work together rather than separate product teams. Returning to his theme that it’s important to have features that make email better, he wants to see those features in all clients. Closing the gap between the different clients is very much on his to-do list.

Bringing a focus to the Inbox

Speaking of which, an example of a feature that should show up in all Outlook clients is the “focused inbox” (see above). Outlook Web App (I refuse to use the new marketing-approved “on the web” name) is expected to get it next followed by desktop Outlook (including the Mac version) and the universal app.

The interesting thing is that Microsoft will replace the existing Clutter functionality that is enabled by default for every Office 365 mailbox. At least, the existing setup where incoming messages are sorted into important email (which remains in the Inbox) and everything else (which goes into the Clutter folder), will be replaced by “Focused Inbox” and “Other” views of the Inbox folder. User feedback from the current Clutter implementation is that it is too easy to overlook important items that have not been categorized correctly and end up buried in the Clutter folder. It’s just easier when everything stays in the Inbox. And anyway, Javier dislikes the Clutter moniker as he thinks it’s too negative. The messages that end up there aren’t really clutter, just less important than the email that you should deal with first.

But the Clutter technology won’t be going away. Instead, the decision as to which view messages show up within the focused inbox will be determined by the Clutter algorithms and the information gathered in the Microsoft Graph about how users interact with email. Think of this as a merge between the advanced artificial intelligence-like technology in Clutter and the user interface that has made the Outlook apps so popular.

Clutter doesn’t exist outside Office 365 but the focused Inbox is available to anyone who uses the Outlook apps, even if Gmail is the server (the focused inbox is one of the reasons why some commentators regard Outlook as the best client for Gmail). Filtering is accomplished by running messages through a rule set, including a sender ranking table (the most important people you correspond with) and whether a message comes from a human or is machine-generated. Javier wants to take this concept to on-premises Exchange too in order that Outlook clients connected to on-premises servers can support the focused inbox.

Presumably this can be done in the form of a mailbox assistant that’s provided as an update for Exchange 2016 and maybe even Exchange 2013. Delivering the focused inbox will come as welcome news to on-premises customers who sometimes feel that they have been left behind due to Microsoft’s ongoing focus on cloud services.

Moving forward

New leaders usually impart a sense of energy and urgency to an organization. Javier Soltero wants to make email better, to deliver simplified but more functional clients faster, and to make sure that all of the clients that make up the Outlook brand share a common base of functionality. There’s a lot of work lurking beneath those statements. Time will tell just how successful he will be, but I hope he delivers because better Outlook will make me happier…

Follow Tony @12Knocksinna