Office 365 is clever - and sometimes just a little bit too clever

What priorities do you want your work email system to have? As Office 365 adds extra features to email, the basics can get hard to find.

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Image: iStock

Office 365 thinks that email is the thing users care about most.

It's probably right, but I still find it a little disconcerting to have Outlook Online be the thing that opens when I log in to the Office 365 portal; this time I actually wanted to look at Delve Analytics to see if it covered Microsoft Teams. (As with everything, there's a setting to change whether you go straight to mail, in the admin portal, but this is the default behaviour.)

Outlook Online has long had all the features of the Windows Outlook client and some features it even gets first: it's easier to introduce a new feature in a web interface tied to an always-up-to-date version of Exchange Online than in a desktop app that might connect to a huge range of email servers. This time, I got something I didn't expect in my work email; Outlook offered to track my favourite sports team so I wouldn't miss any matches. The same message popped up in the Windows 10 Mail client for my work account.

Outlook offers sports schedules

Outlook thinks I want a calendar of sporting events

Leaving aside the fact that I don't have a favourite sports team - I vaguely root for both the SF 49ers (when I can remember that they're not called the Giants) and the Seattle Seahawks (when I can tell them apart from the Mariners) - even if I did, would I want to see their games on my work calendar? It would stop me scheduling an important meeting that would stop me catching a game; if you do care about sports, that might help with your work-life balance. It feels like the sort of feature that would fit better in Cortana though, next to the reminders she gives me if I schedule a meeting in what I've set as my usual lunch hour.

Having dismissed the popup, I couldn't later find where to add a team schedule. I looked in the Calendar settings and discovered that I hadn't turned on parcel notifications, and that Outlook thought I wanted to see weather for Salgotarjan, Hungary. It looks a nice enough place - with a delightful castle on a nearby hill - but as the only place in Hungary I've been is Budapest, over a decade ago, I'm not quite sure why Outlook picked it.

Outlook offers to create calendar items based on email

Outlook can check your mail for travel information you'll need in your calendar - and now for package deliveries

Checking my email, I noticed some new buttons on the message itself. I could click to add the mail to Wunderlist as a task, which is useful but also underlines how badly Microsoft needs to unify its many task management systems, from Wunderlist to SharePoint to Outlook's own tasks. The clock icon next to it opens My Analytics, to analyse all my conversations with this contact; do we talk a lot? Have they sent messages I haven't read yet? Do I usually reply to them quickly? Do I send them more messages than they send me?

icons in Outlook Online

What Outlook Online thinks I most want to do with an email - and it's not reply

The thumbs up icon? Lets me 'like' the message, if replying with a smiley face is too much and not responding at all is too little. It's very social network, and maybe in a year or so I'll come to think of it as a useful 'light touch' the way it is on Facebook. But how do I actually reply to the message? For some reason, that's relegated to the dropdown menu, even though it's the thing I do almost as often as deleting messages (also relegated to the menu, but I can do it from the ribbon or the inbox list, so not as annoying).

options on the Outlook Online menu

Reply is always on the menu

Presumably, if I'd opened Outlook Online in a slightly larger browser window, it might have managed to make room for the reply button too - but the browser window was half the width of a Surface Book screen, which should really be enough space for one of the key features of email.

Reply All button

This time, Reply All gets priority

And when I opened Outlook Online a little later, in the same sized window, the button layout was different again - the Like button was still in pole position but Reply all had appeared where I expected it to be, and Wunderlist was a larger button underneath.

I closed the browser window (well, Edge crashed because I'm on a Windows Insider Fast Ring build and I had over 30 tabs open; I know there are going to be bugs in Insider builds). When I opened it again, the Reply all button was gone again - and then, too quickly for me to capture an image of the screen, it re-appeared, this time with the Wunderlist and Analytics buttons next to it, even though the browser window was still the same size.

Buttons in Outlook Online

Reply All appeared - with all the other buttons


Confused, I start clicking through different messages. Some showed all the buttons straight away; others - conversations with multiple messages - painted in the Wunderlist, Analytics and Like buttons straight away and then added the Reply All button. You might not notice it if you weren't looking.

Slightly obsessed now, I closed the tab and opened it again. This time, it was the Reply All button that loaded first and the other buttons that filled themselves in next to it.

These would be harmless quirks of interface consistency and the way web pages load, if Outlook Online gave you the option to choose the priority of the buttons you see on a message. Instead, Microsoft gets to decide that because you've taken the time to integrate Wunderlist, and your admin has turned on Analytics and the Office team has gone to the trouble of creating a Like button, those should be the first buttons you see.

I adore the increasingly clever features of Outlook and Office 365. I do use Wunderlist quite often. Having flights automatically show up in my calendar or knowing when a parcel is due is definitely handy. Having Clutter filter out the hundreds of marketing lists, random Kickstarter press releases and coupons I get by email is downright wonderful, because it means I can immediately see the (relatively few) important emails I need to do something about right away. Delve Analytics tells me I only reply to 16 percent of my email but thanks to Clutter it's the right 16 percent; Clutter has literally saved email for me as a useful working tool.

In general, I can't praise Office 365 highly enough as a great business combination of commodity email and document storage (as long as you never leave the interface, Microsoft Teams makes SharePoint friendly and usable!) with smart, AI-driven features that are really useful.

But every now and then, there's something that's just too clever and gets in the way. Because once Clutter has pruned my inbox down to the messages I care about, the thing I most want to do is reply to them - and I shouldn't ever find myself wondering where the button to do that has gone.

the Outlook Online interface

The third time I opened it, Outlook Online settled on a sensible arrangement of buttons

Read more about Microsoft by Mary Branscombe

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