Software designed to help set meetings a reminder of subtleties involved in organising every get-together.

The only thing more tedious than going to a meeting is scheduling one, which helps to explain why scheduling-software startups outnumber Republicans running for President.

By the count of Dennis Mortensen, founder of, at least 47 rivals are trying to do what his company does - eliminate the flurry of emails that precedes even the simplest get-together with a co-worker for coffee. may be the most ambitious of the bunch. Rather than an app or email widget, its product is an entirely automated personal assistant. Sign up with and your meetings will be corralled over email by a helper named Amy Ingram or, if you would prefer a male assistant, Andrew Ingram. If you are nerdy enough, you may have already picked up on the joke: The initials for both assistants are AI, as in artificial intelligence, and an n-gram is a technique used in computational linguistics.

If this works, it feels just like having a secretary who can anticipate your needs. But inserting a piece of artificial intelligence into what has always been an all-human interaction is tricky, and not just in computer science. Using Amy for a few weeks is a reminder of how many unwritten rules, social cues, minor deceptions, and struggles for power are involved in every get-together in our professional lives. For to succeed, Amy not only has to imitate a human. The software must also subtly manipulate everyone you work with. If the bots end up alienating them instead, says Mortensen, "I may just be company number 48, and we'll go to the grave with the others."


But it isn't a foregone conclusion that Mortensen's competitors are all doomed., ScheduleOnce and Sunrise, among others, have drawn loyal followers by providing easy ways to set meetings. Google, Microsoft and Salesforce have all snapped up startups in this niche.

Tami Reiss, chief executive of consulting firm Cyrus Innovation, regularly uses three different scheduling apps that allow her to embed in emails a few suggested times to choose from. When the recipient clicks on a time, it's added to both people's calendars.

The trick, says Reiss, is to dole out just the right amount of information.

"I can show you 12 spots if I think you're important. Or show you two spots if I want to pretend I'm important, even if my whole week is free. You can play mind games," she says. "It's very intentional.", which is in a private testing period, isn't that savvy yet. The system took so long to schedule a lunch meeting with one of my editors that we had already eaten by the time he got an email. Mortensen says the delay is intentional; right now he's more concerned with making sure data is collected correctly.

My first thought when using Amy was: There's no way I am trusting this computer with all of my meetings. When my boss' boss said he had to talk to me, I handled that one myself. I also opted for direct communication to arrange a reconciliatory coffee meeting with a source who was annoyed with me. But many interactions whizzed along with no problem, often with people unaware they were dealing with a computer.

I asked Daniel Post Senning of the Emily Post Institute whether I was being rude by tricking people into corresponding with my artificial intelligence. He didn't say yes, exactly. But he did remind me that not everyone is keen to facilitate my decision to live in the future.

"That robot assistant that might be an absolute wonder of efficiency within an organisation might feel cold outside that organisation," he says.


One person who refused to play along was Charlie O'Donnell, a Brooklyn-based venture capitalist.

"I purposely ignored it. I felt weird talking to a robot."

Virtual assistant
How scheduling software works with start-up firm

• The service uses an email "assistant" called Amy Ingram or Andrew Ingram (initials: AI).

• When you want to set a meeting, just copy Amy on your email.

• She takes over by writing to everyone else getting the message to find a time and place based on your schedule and preferences.

• It's based on natural language processing - users email Amy using plain English.