First experiences with Cortana as a scheduling assistant

Recently I signed up for the Calendar.help 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 Calendar.help service works with Office 365 and only requires that you CC cortana@calendar.help 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.

Also published on Medium.