Over the last few months, I have been trialling Microsoft’s AI-based scheduling assistant, Project 'Calendar.help', which is based on the Cortana virtual assistant.


The purpose of the tool is to take some of the hassles away when organising meetings. Rather than trying to coordinate everyone’s diary, you simply invite Cortana to organise a meeting with the required attendees. You can specify if it’s a face to face or a Skype meeting, duration as well as location.


For people within the same organisation, Cortana will check everyone’s calendar and book a meeting with the required parameters if a suitable time is found. If an obvious time cannot be found, the attendees receive an email from Cortana with some suggested times. Attendees simply reply to the email, accepting the times or suggesting alternatives and Cortana will compile these suggestions from all and then book the meeting. See an example below.




As Cortana does all the organisation, it saves you time in having to do this yourself, freeing you up to be more productive. At least, that’s the idea! In reality, things don’t always go smoothly. Some people don’t understand that the communication to organise the meeting is coming from a different email address and reply back directly. Cortana isn’t able to capture this communication and so can’t progress to schedule the meeting. Cortana isn’t currently able to factor in travelling time, so sometimes you can have meetings scheduled back to back but no time to travel between locations.


When it works, it works well, and I have been impressed with the time saving for organising meetings. It works particularly well for meetings within the same organisation as Cortana can easily see free/busy information for everyone in the organisation, subject to organisation configuration. 


The product is still in beta, and sometimes, it can take a while to organise the meeting. Microsoft suggests that Cortana should start organising within five minutes of receiving the meeting request, and in some cases that has been the case. I have had one or two meetings where the scheduling hasn’t started for a number of hours though. I assume that this is a resource issue in the beta.


This is a tool that focusses on one thing. It has great potential when some of the niggles are ironed out. Once it can plug into real-time traffic, work out travelling time, connect to a suitable venue, book lunch, send directions directly to the car sat nav, alert you when its time to set off etc. it has a serious potential to save lots of time and make your day more efficient. It's not quite there yet, but it does give a glimpse at the potential for virtual assistants and AI in the future.


For more information about this tool, please visit calendar.help.