Artificial intelligence technology is EXPLODING! I read articles every day about how computers can “think” more and more. They can analyze your photos, interpret your conversations, learn from your habits, predict your needs and much more. It’s creepy, yes. But it’s helpful. And, like it or not, it’s coming. Fast.

This week I put an AI provider through a number of tests. offers a virtual scheduling assistant, a service they’ve given the name Amy Ingram (for AI, get it?). Amy has a brother named Andrew, if you’d rather have a male assistant. The idea is that you can copy Amy on your emails when you’re trying to schedule a meeting with up to five people. Amy works directly with your attendees to find a time to meet. She “reads” meeting requests and responses as you write them in natural language and once people settle on a good time, she sends an invite to everyone. just emerged from beta. They have a 14-day free trial, which I am using to try it out. The lowest paid version is $39 a month, and soon they’ll offer a free plan that lets you schedule 5 meetings a month.

With help from some of my most active newsletter readers, I used Amy to schedule a number of calls so I could ask them what else Your Nerdy Best Friend can do to make our community more valuable. I chose to tell everyone that Amy did not exist.

The results were mostly positive and very interesting. I plan to schedule about 20 or so calls/web meetings during a three-day period, and we’re about halfway done. I like how you can check on the status of all the meetings she’s working on, and you can see the history of all the emails she sends and receives (except for the original one — that would be helpful, too).

Bottom line: Would I subscribe to the service? Nope. I think the personal touch is critical, and my manager, Molly, does it better than Amy ever could. But if I was scheduling lots of meetings with perhaps job applicants or vendors, I think the service could save time, money and effort in the long run.

Assignment 1: Request for a 15-minute phone call


Amy sent out three possible times to my first person, and she quickly accepted one of them. Amy asked for a number to dial, and Sandy responded with her first message.

Email Summary:

  • Me inviting Sandy and CCing Amy
  • Amy writing to Sandy with three alternatives.
  • Sandy accepting.
  • Amy telling Sandy that she’ll send out an invite.
  • Amy sends out an invite to both of us.
  • Sandy accepts invite.

An annoying point: Amy has full access to my Google Calendar, so I was quite surprised to see that she didn’t automatically put the confirmed meeting into my schedule. Instead I had to accept the meeting. It’s a small task, but if you’re trying to cut down on your own emails and tasks, it seems to be an unnecessary step. Another annoying point: When Amy puts the event on my calendar, she does not include Sandy’s email — just the phone number. It would be handy to have all the info about the meeting in the event on the calendar — including the original email, for example? I just received a new tip email that talks about a new feature that lets you tell Amy what the title of the meeting should be, but that’s not necessarily enough info.

Assignment 2: Request for a 15-minute call with extra info


Amy wrote with three alternatives. Jennifer chose one and asked Amy if someone else could join the call. Amy could not process this request, so she sent the note to me asking me to follow up directly. An annoying point: Amy did not include Jennifer’s email in her note so I had to go look it up. This may not be as big of a problem if you’re scheduling one meeting a time, not scheduling a whole bunch of calls at once like I am.

Amy wrote to Jennifer to let her know that I will follow up but asked for the number. Then she confirmed and sent out invites.

Assignment 3: Request for a 15-minute call with Fran and Molly together


Amy sent separate notes to both Molly and Fran with the same dates and times. Fran was the first to choose one. When Amy received the note from Fran, Amy wrote to Molly to update Molly on Fran’s preferred time. Molly confirmed the time. Fran and Molly were both sent details of my conference call line (Zoom). Note that I had already loaded the Zoom info into my preferences.

Assignment 4: Requesting a specific dates


Ginny said she could only meet on 11/29, so I sent Amy a note asking her to schedule a call on 11/29 after noon CST. Amy wrote to Ginny and offered 11/30 and 12/1. I wrote to customer service to ask about this one.

Two days have gone by since my note to customer service, and I haven’t received a reply. But their latest tip email said this:

Being a human boss to an AI personal assistant raises some funny questions: Do you thank Amy? Say “please?” Let people know she’s AI?

And what about mistakes? Amy & Andrew are great at scheduling but they’re not omniscient. And sometimes they just mess up (yup, we know). So what to do?

First, have a little bit of patience. Usually you can correct Amy and get the meeting back on track, e.g. “this should be 2pm ET not PT” or “Amy no need to email John – the meeting is for Samantha and I.”

Second, get curious. Sometimes Amy is just doing her job, and it’s the human (you or your guest) who has erred. Usually, a quick trip to your meeting history page will shed light on the problem.

If you’re still stuck, reach out to human help ([email protected]). They can sort out your meeting and make sure you’ve optimized your settings for Amy’s success.

Last, we’ve found that setting up 13 meetings is what it takes to get a new assistant like Amy into the swing of things. Know that we’re here to help you get there.

Assignment 5: Negotiating a back-and-forth between participants


It’s important to note that everyone you include on an email will be asked to join a meeting, even if you specifically ask Amy to schedule with just certain people. I copied Molly on a request for a meeting with Christine, and now Amy is stuck in a loop trying to negotiate a time they can both meet.

Christine chose a date, but Molly proposed another one. Amy has now sent two extra notes to Christine to ask her if other dates will work. Christine has not responded yet. In the FAQs, I read that Amy will try three times. I’m interested to see if she’ll send more notes.

Assignment six: Requesting a web event and including the link


Every time I mentioned that we would have a web meeting, Amy wrote me back asking for the web meeting link, so I included the link in the original schedule request with Yiftach.

Amy, could you set up a 15-minute web meeting with Yiftach? 11/29, 12/1 or 12/2 will work. The meeting link is

When Amy sent the invitation, it included the web link.

Assignment 7: Avoiding pissing off your attendeees


A special note about Yiftach: He is really annoyed by AI but intrigued by this experiment. Here’s the note he sent me to request to be on the calls:

RE: “A virtual assistant named Amy Ingram”

I don’t know that I could be called one of your “most active community members” but I’ll tell you what I want to see stop in 2017: this. People giving names to their AIs, especially names with the initials A and I. (I know you didn’t make this, and I don’t even know why it’s annoying to me, but it is.)

Two days later after he successfully confirmed his appointment with Amy after his request for a time shift, Yiftach wrote this:

Gotta say, Beth, I’m pretty impressed so far. And not annoyed even a little.

Future assignments: Throwing Amy some curve balls

I didn’t want to annoy my nerdy friends by experimenting too much, but I’d love to know what Amy does in the following situations:

  • What if I book another appointment into a slot that Amy offered to someone else? When the attendee accepts, does Amy write back to say that the time is no longer available, or does she just send invites?
  • What if I want to add another attendee to a meeting invite after the invite has been sent out? Does Amy go back to the original person and the new one to negotiate again?
  • What if I send out a lot of invites again and two people ask for the same time? Amy seemed to do a good job of staggering the meeting times (she asked the first person if they wanted to meet at 9 and the second if she wanted to meet at 10, for example).

This article was originally published on and can be found here.

I lead,and I do so with the fiercest of passion. Along my journey, I have been lucky to meet association professionals who choose this field because they believe in its power, and dedicate their time to furthering it. It is my job to bring these people together to solve problems, and this is the very core of my raison d’etre!

I lead,and I do so with the fiercest of passion. Along my journey, I have been lucky to meet association professionals who choose this field because they believe in its power, and dedicate their time to furthering it. It is my job to bring these people together to solve problems, and this is the very core of my raison d’etre!

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