Amy is a software platform provided by which provides automated scheduling. Need to book a meeting? Amy's there for you. Need to reschedule? Amy can do that too. 

I've been using Amy to book meetings since 2017 (when it was priced about 5x what it's currently priced at) and I think that they have done some amazing things with that platform. Out of the solutions that companies get nickeled and dimed on with annual subscriptions, Amy is worth every penny.

Here's some things that I've learned from using Amy over the past few years:

Ease of ‘Installation'

The team did an amazing job of making it easy to set up Amy. They created wizard-like interfaces to connect your email and support every major email provider. Literally in less than 15 minutes and for less than $10 per month, you have a new AI Assistant.

Amy Trains You

When you first set up Amy, there is a little bit of a learning curve. You need to use language that Amy understands and she tells you exactly what she needs. She provides you with best practices on how to specify dates, times and locations. She also teaches you how to account for driving time if needed between appointments.

When you initially sign up for Amy you get added to a very sophisticated drip email campaign. They send you the basics of how to get started, then as you get more familiar with the platform they send you best practices on many of their features. Just seeing how they onboard a customer for a fairly complex product is worth the price of admission.

Amy is Gender Neutral

When designed Amy, they also created her male counterpart Andrew. The amazing thing is that the language that Amy uses is identical to Andrew. 

Designing conversational interfaces is challenging but when they designed Amy/Andrew, they had some key tenants:

  • Politeness & Professionalism: they identified some key attributes of great admin assistants: they generally respond in about 15 minutes, they are brief and polite. They have a way of making it look like your calendar is full.
  • Friendliness (but not of the overly cheerful, many exclamation point variety): People have actually asked Amy out on dates, however she is scripted to politely decline the offer.
  • Clarity: Amy was optimized to propose times and make the number of back-and-forths as few as possible.
  • Empathy: When people start to get frustrated or after a certain number of interactions, Amy will respond differently.
Amy is Designed to be Human-Like

About 80% of the time when I have a meeting scheduled via Amy when the person is not familiar with, we jump on a call and immediately I am asked if we are waiting for my assistant Amy. At this point I have to laugh and point out that Amy isn't a person, it's a robot, but it always cracks me up.

Amy Doesn't Always Get it Right

You can deviate a little bit and she'll still get it, but stray and try to trick her and all you'll get is a confused bot that you need to interact with. Recently I initiated a meeting via a website form submission which automatically sent an email to Amy and the form submitter that says ‘Book a meeting for next week'. The recipient of the email got the email from Amy who asks what time works bests. The recipient replied any day before September 8th which was completely off the reservation. Now I need to intervene to get the meeting scheduled, however, I must say that Amy is politely reminding me that the meeting still hasn't been scheduled.

Additionally, Amy stores the conversation logs so you can see where it went off the rails – super helpful again in learning how better to use your new AI assistant.

Overall Summary

Overall, I think that Amy is the best use of Natural Language Processing available in the market today. The team at have really outdone themselves in terms of creating an AI that is useful, high quality, and has an amazing onboarding process. I highly recommend you check it out, and if you want to use my referral link, that would be fantastic.

To learn more about how designed Amy and some of the training Amy went through, you can see their article here.

To learn more about what to consider when designing conversational interfaces, this is the best book that I've found on the topic: Designing Bots by Amir Shevat

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