A lot of companies are trying to “solve” calendars.

There are many startups that are building calendar apps, desktop apps, and combinations of the two.  Some even try to also manage your to-do list. Integrated features like knowing background information, lateness notifications, and notes on important details about people or places – all part of the race to “own” your calendar.

The goal of course is that you are weened off of the standard/default calendar that comes with your phone/tablet/computer/OS and you use their app instead. This of course is a great lock-in for the app makers for it increases the switching costs to another calendar or service.  If you are tied to the “extra” features of a calendar like to-dos, notes, cumulative info – it can be hard to switch to something else.

I believe a missing thing they should be going after is solving scheduling. Whether it be meetings, calls, reserving times that work, or anything else you need to do involving blocking time off in your schedule.  It has been said many times elsewhere, but the best way to see someones priorities is to look at their calendar.  Its almost like a to-do list with your time and some even say that if its not scheduled in your calendar its not important.  Blocked time in your calendar visually shows your priorities.

Most calendar apps miss showing the simplest thing for me – showing free time on a day view. The benefit of this for me is that I am constantly adding/removing meetings and things on the fly and need to know the windows of time I have available.  Either checking while on the phone, in a discussion, or in real time trying to reschedule something viewing the free time is critical.

I am using the Google calendar system of record and pushing that to my iOS view.  This does make things easier and in some ways it means that Google “owns” my calendar.  I have heard that this also means switching back to native Android would be that much easier.

Knowing that this free time view is crucial, I always look to see which apps provide it; either on the desktop or mobile. Perhaps it is just not as important to others but many simply do not have this view built in.  All shows you when things are booked, but not when you have time.

My workflow is always to open my email in the morning, open another tab with my calendar, then dual wield between the two all day. Through the rats nest of Google Calendar settings, I have figured out a way to manage and edit both my work and personal calendar – no small feat.  It means that I can view my personal and professional calendars together and still invite people in both worlds to events.  I have reached a point where if I do not put something on my calendar I may forget about it, so I try to put every meeting in it.

Calendar App Wishlist

  • Desktop app – Having a calendar open in another instance of Chrome is a pain.  Opening the two and switching between them all day seems like a waste, but without the free time view, I don’t see another way.
  • Mobile app – syncs flawlessly with work + personal and shows free time view
  • Background info – Rapportive style background on people.  Refresh does this today, but its background on the people and secondary to the Calendar itself, not a replacement
  • Simple sharing\editing granting permissions – As mentioned above Google allows this, but its a nightmare of settings and sharing functionality
  • Default meetings times = 30 minutes.  Simple enough request, but Google Calendars makes this fixed to 60 mins. (Ideally I would get to choose the time for the default meeting)
  • Weather/Foursquare Location/Distance to travel <–easy metadata to make any appointment that much easier
  • Future proofing; interior location monitor if I am not where I am supposed to be, notify someone automatically that I will be late, ping me if I am not moving towards my next meeting, sync up latest emails with that person into cal., oh and lasers

My calendar workflow for meetings

1. Setting up a meeting via email

The best add-on I have found for managing meeting requests without all the back and forth is Boomerang Calendar (free!).  It automatically lets you click times that are open (in 30 minute intervals!) and inserts them into an email to someone.  Its one of the biggest time savers possible, and avoids a ton of back and forth that usually happens with scheduling.  I wrote about appointment setting etiquette, but I respect the fact that everybody is different.  I get multiple “can you meet this week?” emails often and always follow my own rules to respond back with 3 times/3 dates.

2. Logistics

Picking a time or place can be cumbersome, so I always throw out a dial in to the group.  I use TextExpander (paid but worth it) to have my info ready, and this way I always know my own dial info and code.  This way no matter where I am, I know I can dial into the meeting with the right info.  I used to use FreeConferenceCall.com but have found the latency is just not worth the broken conversations.  Investing in a rock solid conference line is worth it.

Pro Tip: You can program in your own conference call info into favorites, program in pauses with “,”‘s and have it automatically dial you in, enter your passcode, as well as the admin code.  This probably saves me the most time each week next to Boomerang Cal.  To put it another way, I can click “Conference Line” and my phone will automatically deal with the prompts/codes/admin code for me and get me dialed in fast.

3. Locations

When meeting someone in person outside my office, its best to know/pick a spot nearby.  Perhaps its just a personal peeve, but going back and forth on a place is hardly worth 4 emails – I cut to the chase and offer up nearby coffee shop/diner/other.  I am clearly biased, but using Foursquare is honestly the best way to find a place that accommodates meetings.  Lots of people leave great tips at coffee shops letting me know whether its good or not.  Here is a great tip at Grey Dog in SOHO saying exactly what you want to find for a good location.

This post is a bit of a rant, but I am trying to get back into the drivers seat of writing more blog posts in 2014 :)