Working in a hectic, Mac-first environment, Apple Calendar is probably one of my top three productivity tools. On workdays I live from my calendar and it’s one of the very few apps for which I haven't turned my notifications off.

Traditionally, calendars where used for scheduling and tracking date and time bound events. The mechanics where simple: when scheduling an event (often way in advance), you consulted your calendar to see if nothing else was planned on that time and date. In other words, calendars had a ‘date-and-time-first’ use case. This concept translated perfectly to the digital domain, providing additional functionality like remote acces to other calendars, searching for specific events and verifying availability to make this process quicker and easier.

However, today’s business settings adds more variables to the mix. Next to much denser calendars, you deal with more invitees, the requirement of meeting rooms and perhaps even multiple office locations. From that perspective, a ‘people-and-place-first’ use case would be a better approach for a modern digital calendar.

1. Working locations
Some people (like myself) work from a different office location several days per week. Unfortunately, Calendar doesn’t natively allow me to communicate where I am situated on a specific day. This is mostly relevant for someone else wanting to scheduling an appointment with me. I solve this by planning an ‘all day' appointment for myself with my location as a subject.

But manually looking up someones location when needing to schedule a meeting is an inefficient process. Moreover, several invitees means several manual calendar inquiries. Therefore, having a dedicated feature for a working location is a fundamental component in improving the calendar’s functionality.

2. Native meeting room booking
Whenever I want to schedule a meeting with a meeting room (which is pretty much 95% of the time), I need to switch to either calendar.google.com or to the Google Calendar app for iOS to add one. This is by far my biggest issue with Calendar at the moment. There are workarounds, such as subscribing to all meeting rooms calendars (that’s 35 for our two offices) and then manually check the availability of random meeting room, hoping to get lucky. It would be much better if I could just pick an available meeting room from a list within the appointment itself (given that I’ve already provided a date and time). This could be part of the location selector, or could be a separate input, just like in Google Calendar.

3. Context-aware rescheduling
When one of the invitees declines, I have to reschedule the meeting which forces me to repeat the earlier mentioned sequences for locations and meeting rooms. But being able to have these variables natively, allows the calendar for 'smart rescheduling'. In other words, the calendar can automatically suggest me a new date and time if an attendee declines, taking into account the following:

  • All invitees are available on the that date and time
  • We are all on the same location (if required)
  • There is a similar meeting room available (if required)

Moreover, users can mark this as an 'In person' meeting (i.e. we are both on the same location that day) and/or I can set this as a 'video call’ (adds a google hangout link to the description). I chose checkboxes instead of radio buttons so I don’t have to add in a third ‘null’ choice (i.e. to deselect).

4. A smarter way of quick adding
Finally, with all of the above features in place, calendar would now also allow for a smarter way of quick-adding appointments. Instead of the ‘pick-a-time-and-adjust' approach, I can now start by adding invitees and see what time and place is the next possibility.

I believe that these optimisations would greatly enhance my Apple Calendar experience, and probably that of thousands of others. I realise that some of the issues need to be fixed in the CalDAV protocol rather than just in Calendar as a client. The point of this article is not about formulating a conclusive technical solution, but as an exercise of working back from the experience to the technology. I hope you liked it.