Cortana Calendar-Scheduling Queen!

An introduction to + how you can skip the waitlist and use this game-changing feature now. I had planned originally after my first blog post to post at a higher frequency, but with my new role at Catapult, I’ve been so busy! I imagine you are too, so let’s get to the point: here’s a post about a Cortana calendar and how she can help us all save some time and sanity.

I’m constantly striving to structure my weeks more efficiently, but when I tried to audit how I’d spent my days, I kept running into these time gaps that I couldn’t account for.. Until… I finally realized that these “mystery gaps” included the time I was using to schedule meetings. How could I somehow reclaim this time? I already had the FindTime add-in for Outlook, and that worked okay, but still resulted in time lost and sometimes too many options. So, Cameron Fuller, being my mentor for this new role, recommended I had already been using Cortana to help me track packages and to remind me about the commitments I had made via email, so I immediately hopped on board with Cameron’s suggestion. I knew Cortana would use AI to offload my calendar management, and that she’d have no trouble removing some of the back and forth from my scheduling, helping me focus better on my work, as well as on the people I needed to meet with.

So, how does Cortana Calendar work?

Cortana calendarWhen I find myself in a back-and-forth email thread where it seems more appropriate to just meet in-person or over voice/video, I use the Outlook mention feature (@Cortana), and it adds her in the TO: line. She picks up on pronouns like “his” and “her” when scheduling, so I speak to her using natural language, as though she were my real-life assistant (most times I even say “please,” which feels weird when I think about it). This is how it looked when I needed to have a monthly 1:1 with my Director:

What if I can’t be in-person? Well, I just specify the location as “Skype” the same way I would ask any other person to add a Skype bridge. As of this posting, scheduling on Teams is not yet available, but I did get in contact with the product team responsible and they assured me it would be coming SOON*.

Here is what the request looks like on the other side.

Cortana calendar








Responding back to Cortana in natural language, “4pm works for me” is all you need to do!

Cortana calendarThis is all great, right? But what about the people who aren’t on O365 yet—does it work for them? Yes! If you’re using a Microsoft or Gmail account, you can sign up. I signed up with my work account (O365), my, and My addresses just to test it. When you sign up with a Microsoft account, you will get the following prompt (but this didn’t happen with Gmail).




Did I really save any time using this?

I think I did, and thankfully there were some metrics to back up my conclusion. I was able to go to the stats tab once I signed in at and review on a weekly basis how many requests I made and how much time it assumed I had saved.

Cortana calendar







How do I sign up?

Cortana calendarTo sign up, go over to This feature is an exclusive preview right now, but if you’d like to skip the waitlist, follow me on Twitter and send me a message! I have also made a short infographic to summarize this post!



PS. In case you were wondering about the other Cortana stuff I mentioned, here is an example email. We can dig more into Cortana native features next time.
Cortana calendar

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