Like many people I have multiple calendars – I have two work calendars (don’t ask) and a personal calendar. This isn’t that weird when you think about the fact that you get a calendar with Gmail and often at work you’re forced¹ to use some form of Microsoft Office (either on-premise with Exchange or online with Office 365). And maybe you are an advanced family and have a shared calendar somewhere as well – although this scenario is not common, most families still use a whiteboard or post-its on the fridge.
The problem occurs when you want to schedule time with someone – you have a single view of your calendars thanks to iPhone, Android, etc. but you cannot see their free/busy since a) it’s often not shared and b) it’s split between multiple services.
Hailstorm – in 1999 we worked on a variety of cloud services (we didn’t have that term yet) one of which was MyCalendar. The idea behind MyCalendar was that it would pull the data from each of my different calendaring services and make them into one. That way anyone wanting to schedule time with me could see my free/busy (with permissions of course) and schedule appropriately. Hailstorm was a great idea canceled too soon². But here we are in 2018 and we still have not solved this scenario.
There are a few services out there that try to help:
- Doodle – this is more for group scheduling and isn’t very useful with how people really want to schedule time.
- Calendly – great service when you need to ask someone to book time with you – but it still doesn’t work for *their* calendar service which is what is needed. I pay for this service especially as I interview a lot of people and need to not spend time emailing back and forth asking for open times.
- AI services like x.ai – these are tackling the problem a different way i.e. having an AI bot handle your multiple calendars and the rigamarole of emailing back/forth. These are basically trying to replace a bad system (calendars) with a bad solution (human assistants). Opinions vary on how well these assistants really do; I’ve seen things work well and I’ve seen conversations go off the rails.
Why doesn’t someone build Hailstorm’s MyCalendar. It’s a simpler problem to tackle today then it was in 1999. Most calendars are online. Most export free/busy. Many can be integrated today using OAuth as witnessed by Doodle and Calendly. Given that I am paying for Calendly now I’d be happy to pay for a service in which I could tell people “my calendar URL is here, grab whatever time you need” and it just worked.
¹ No one chooses to use Office – it’s a decision that is steeped in corporate lore and at this point it’s a barnacle. If you start a new company you might get to use a decent collaborative tool but if you have an existing large business it’s too late, you’re trapped in the 90’s forever.
² Hailstorm was canceled for many reasons. We pitched an ad-based business model but Microsoft wasn’t ready to accept that concept; to be fair Google was still a year or two away so who knew it could work? Many teams were also worried about canibalization e.g. Exchange worried about lost sales if we did Email in the cloud. Oops, turns out that was going to happen anyway. And there were legitimate concerns that we couldn’t actually build and operate the services we were promising.