First experiences with Cortana as a scheduling assistant

Recently I signed up for the preview which effectively has Microsoft’s personal and productivity AI Cortana help me schedule meetings.

At present when working with Office 365 there are a number of ways to schedule meetings with people outside your organisation:

Left to right scales from simplicity to most complicated. When scheduling with multiple people in different organisations it can be quite complex, which is where Microsoft FindTime plays well.

The service works with Office 365 and only requires that you CC to begin the process. This is nothing really new as there are a number of scheduling assistant bots out there.

The experience is relatively simple and when initially setting up your profile you are asked to set some preferences such as timezone and preferred meeting times.

While Cortana can see my calendar and work within my availability, I am not sure if it is doing any consulting with the calendar of the person on the other end.

From my limited testing if you schedule a meeting with someone internal – it appears Cortana can check their calendar and therefore automatically enters the appointment into their calendar.

However, if the user is external they are presented with a variety of options to choose from. So, if I suggested Wednesday afternoon or Thursday morning – those are the options Cortana provides to the other person.

After the meeting is scheduled Cortana lets me know what has been booked in. At this point the meeting is just for a call, but I can simply reply back and ask her to make it a Skype meeting which she will go and create automatically for me.

Overall a relatively straight-forward and simple experience, I look forward to doing it with real people once I come back from holidays.

The below Sway shows some screenshots of the email communications both I as the meeting organiser see, as well as the person on the other end.

On a personal note I’m not 100% comfortable using a bot to schedule meetings as I feel it’s a bit impersonal, but as we become more comfortable with bots acting on our behalf it may soon be acceptable.


Challenges connecting Cortana to Office 365

In my previous post I spoke about the fact that Cortana only appears to work on Windows 10 if you are signed in with a Microsoft Account.

Now that I had this working I was eager to connect Cortana to Office 365 and get some valuable insights and interactions.

Our first step is to access Cortana’s notebook:


Once here we see that Office 365 is set to “off”, so let’s set that to “on”:


We’re now prompted to connect, and are presented with the fact that Cortana will now have access to things she previously didn’t have:


Now let’s authenticate to Office 365:


And now we… wait what?


I went to the Office 365 portal to find that Cortana was turned off (I could have sworn it was set to “on” previously).

I turned Cortana on (again, I think):


Then I went through the process of connecting again and presto!


It is important to note that for Cortana to work you will need to make sure the Windows 10 Mail and Calendar apps are also connected to your Office 365 account.

Now let’s see what happens from here!


UPDATE: It is confirmed via Microsoft KB 3086254 that Cortana will not work with Office 365 if you are signed in using your Azure Active Directory account.