Amy Amy is the nicest, most patient scheduling assistant you could ask for. She doesn’t get cranky or tired or annoyed. She doesn’t bristle when you tell her for the umpteenth time that you can’t make it on that day at that time and could she try this other time instead?

She doesn’t get cranky or tired or annoyed because she’s an AI agent.
She’s an algorithm.
A robot.

So, how does she sound so human?

Turns out, the taxonomy of scheduling things is not massive. But it still takes talent to make Amy challenge the Turing Test, which she is not designed to do. She is designed to be a techretary for the sole purpose of putting you and your fellow humans together for a meeting.

Why am I writing about this on the eMetrics blog? Because this is another, soon-to-be-successful start-up from Dennis Mortensen, former Board member of the Digital Analytics Association and I love watching him succeed.

Testing Amy

I decided to put Amy to the test with the help of the erudite and technically savvy Mark Gibbs.

I sent Mark the following (copying Amy):

Hey Mark –

How about lunch sometime next week?
Amy, can you help us find a good date and time?

What followed, was a very human-like conversation. Granted, we were testing Amy – not really fair, but very interesting.

Amy to Mark (forwarding me a copy):

Hi Mark,

Would you be able to meet Jim for lunch next Wednesday Jul 30th 12pm or alternatively at 1pm – or the day after Jul 31st (Thu) 1pm (PDT) ?


Me to Amy:

I can’t make it next Wednesday

Amy to Mark:

I wanted to follow up on Jim’s availability. Jim isn’t available on Wednesday after all, so how about Thursday, July 31st at 1pm PT?

Me to Amy:

I’d prefer noon.

Amy to me:

Hi Jim,

Got it, I’ll follow up with Mark to see if he would be available at noon on Thursday, July 31st.

I can see that your personal preferences do not yet hold a default location. Can you tell me where you would like to meet for lunch?

I’ll remember the location, as an option for next time, so I have to bug you as little as possible.

You are also welcome to email me your favorite meeting places like your office, conference bridge, mobile phone number, Skype ID etc. for future meetings, so all you need is to tell me is how you would like to meet and I’ll fill in the details. Easy.


Me to Amy:

How about Sly’s in Carpinteria?

Amy to Mark:

Apologies for the multiple emails, but Jim would prefer noon on Thursday, July 31st.

Let me know if that would work for you.

Mark to Amy:

I’m slammed next week although Wednesday would work if you’re willing to come to Ventura … Wood Ranch, 12 noon?

Amy to me:

Unfortunately, your guest isn’t available Thursday or Friday.
Would you like me to schedule this lunch at a later date?

Me to Amy:

How about next week?
I’m good Monday through Wednesday.

Mark to Amy:

Tuesday, Aug 05 at 12:00pm will work. Now, the question is where?

Amy to Mark:

Thanks for letting me know your availability.  What about Sly’s in Carpinteria?

Mark to Amy:

Would Wednesday Aug 6 work?

Amy to Mark:

Wednesday, Aug 6th at 12pm works. Will you be able to meet Jim at
Sly’s in Carpinteria then?

Mark to Amy:

Yes, that works.

Amy to Me:

Thank you for letting me know. I’ll send the invite out shortly.

Which she did and Mark and I accepted. The, as always happens…
Mark to Amy on the morning of our lunch:

Alas, I must reschedule … Will next Wednesday work?

Amy to me:

I see that Mark is no longer able to meet for lunch today,
and that you are available next Wednesday at 12pm. 
I’ll send out an updated invite.

And she did.

Amy: Smarter Thank You Know

This gets a lot more interesting when you share your calendar with Amy. She not only knows when you are booked, but starts to learn your preferences.

You generally don’t like breakfast meetings.
You never have meetings on the weekends…. unless it’s one of these five people.
You like to join your daughters at Friday Family but you don’t block it out, It looks open, but it’s not really open.
You are willing to make out-of-office hour phone call exceptions for a friend in Australia because of the time difference.
You only meet with certain people at their office.
An A list person can cause a C list person’s meeting to get rescheduled but never vice-versa. B list people are a bit trickier.

How does Amy learn all this?

You already have thousands of examples in your calendar, going back over the waves of time. You have generated your own Big Data and given Amy permission to sift through it. This is the genius of Amy using email rather than texting for example. Sometimes, she needs more than a few milliseconds to make the best recommendation.

But soon, your relationship with Amy deepens. You tell her your three favorite places for lunch, whether you prefer to meet people for the first time over the phone, in your office or in their office and to never schedule a meeting between just two people for more than 45 minutes.

Amy can also apply temporal logic between in-person meetings, but she’s not looking at real time traffic – yet. This is just one of the million things she’ll be trained to do over time, along with the delay of vertical travel in places like Manhattan. As Dennis put it, "The whole endeavor sounds like a weekend hackathon, until you jump into the pool."


It will take approximately three days for you to forget that Amy is not human and life gets better once you do. If you think of Amy as an AI Construct then you try to communicate in terms of algorithms and structured queries. It’s much easier to use your normal, human syntax patterns. You don’t have to switch mental gears and it doesn’t slow Amy down at all.

Remember, Amy is not just your techretary, she schedules meetings for many, many others and is learning about how humans like to schedule meetings as a species. A great deal of that learning pertains to you as well. The magic happens because Amy is not Siri. Amy has one job to do and, therefore, can do it very well.

You will soon come to believe that Amy is actually 4,000 humans working through Mechanical Turk. You will be wrong.

Now, all I ask is that Mark doesn’t have to reschedule next week.

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