At Long Last, Some Scheduling Help

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Business Calendar & Schedule

Beginning in early March when I was lucky enough to get into the beta (which is still closed), I’ve been using X.ai’s automated personal assistant Amy to schedule meetings for me. The only real problem I’ve had using the technology has nothing to do with the technology. My issue, rather, is one of etiquette. The artificial intelligence behind Amy is good enough that with the exception of people who’ve heard of her, most people never realize they’re communicating with a bot. Which is a credit to the service, of course. But it leaves users with an important question: do I have to tell people on the other end that Amy’s not a person? Should I tell them?

Now you might be thinking that if the worst problem you have is with a new service is etiquette-related, that’s a good sign for the technology. And you’d be right.

As some have noticed, I have a long and unpleasant history with scheduling tools. As an analyst, a big part of my job is to talk to a lot of people, which in turn means that scheduling is a big part of my job. Which explains why I have tried, at one time or another, virtually every scheduling tool known to mankind. Some were people based – things like FancyHands. Others were services, some of which are still around, some of which have retired and one or two that have been forgotten entirely: Appointly, Bookd, Calendly, Doodle, Google Free/Busy, MyFreebusy, ScheduleOnce, Sunrise and on and on. None worked for me, though some were less bad than others. Which is why I still waste time – whether it’s mine or Juliane or Marcia’s – scheduling meetings.

The root problem with all of them, even MyFreeBusy or Tungle which generated the fewest complaints for our usage, was that it was one more moving piece in an already too complicated process. Request is made via email, check calendar, check third-party site, back to email, hope the slot is still open – rinse, lather, repeat. This was because the technical approach that most of the tools took was to implement an outboard, externalizable version of my calendar.

X.ai’s Amy breaks with this tradition. Instead of reproducing my actual calendar minus the private meeting details plus some booking features, Amy replicates a person – a personal assistant, more specifically. Scheduling from my end is very simple: I email back that I’d be happy to schedule a meeting, CC Amy and shortly thereafter I get a meeting invitation in my inbox. She (or he, X.ai has a male counterpart) does the legwork on the back end via nothing more complicated than email and I end up with an appointment on my calendar.

In terms of process, it’s in truth not that different from my end than sending an email saying I’ll take a meeting and including a link to my Tungle calendar. But I never have to explain what Appointly/Bookd/Calendly/Doodle/MyFreebusy/ScheduleOnce/Sunrise/etc is. I never have to field feedback about how the UI is confusing. I never have to explain the difference between a given service’s version of my calendar and my actual calendar, that just because requested an open slot slot on the former does not mean it’s written and confirmed into the latter. And perhaps most importantly, anyone can find and make a schedule request on a public calendar – which means I can be spammed with non-relevant requests. The only requests Amy schedules are those I’ve explicitly asked for. Big difference.

Amy’s not perfect yet. It’d be nice if I could whitelist email domains from clients, for instance, so that they could schedule me via Amy without having to ask me first, and book me for 60 minute increments while non-clients are limited to 30. There is a learning curve as well; used to a settings page, it wasn’t obvious to me at first that setting defaults like my conference number, weekday availability and so on would be done just by emailing Amy. There is also no way currently to grant her access to my colleague’s calendars to make group scheduling of multiple analysts simpler, or group features in general.

But as I said back in 2005, however, the scheduling space has been crying out for innovation, and Amy delivers that in spades – even if I’m not quite sure what the etiquette is for her usage yet. Here’s hoping we see artificial intelligence like Amy employed in many more use cases down the line, because she’s already made my life better just by tackling my calendar – who knows what else she could fix.

In the meantime, we’ll be waiting for access to open up so I can get my analyst colleagues on board, because I can’t see any reason not to standardize RedMonk on Amy as soon as she or it is publicly available. It’s that good.


  1. It’s yet another thing to log into. It might move things forward a bit, but essentially I’m sick and tired of being invited into Yet Another Service. We need native capabilities in every calendar to do all this. Would we accept email that didn’t have cc: for example? The problem is not demanding a richer feature set from every calendar.

  2. @Scott Mace: There actually is no log in with Amy. There’s nothing to log in to, in fact. Email is the interface.

    As for the richer feature set, I’ve been waiting for that for over a decade, so in the interim, I’ll take Amy’s approach.

  3. Good to know there’s no login. What’s their business model? Let me guess – that comes later.

  4. No login even for the sender? How does it prevent someone from spoofing your email address to send out specious invites if that’s the case? Sounds like a new spam pathway if so.

  5. @Scott Mace: No login for the sender. Not sure if Amy is parsing the email metadata, but I can’t say I’m particularly concerned about someone going to the trouble of spoofing my email just to secure a meeting with me.

    Because it would easy to figure out what happened, and embarrassing to be caught at it.

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