Scheduling-software startups multiplying.

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

By the count of Dennis Mortensen, founder of X.ai, 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. 

 X.ai 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 X.ai, 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 A.I., as in artificial intelligence, and an n-gram is a technique used in computational linguistics.

When you want to schedule a meeting, just copy Amy on your email. She then takes over by corresponding with everyone else receiving the message to find a time and place based on your schedule and personal preferences. The system is based on natural-language processing, which means users communicate with Amy by writing emails in plain English.

If this works, it feels just like having an administrative aide 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 X.ai to succeed, Amy not only has to imitate a human, passing a sort of Turing Test. 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.” 

Competitors such as Assistant.to, ScheduleOnce and Sunrise have drawn loyal followers by providing easy ways for people to manage their meeting times. Google, Microsoft and Salesforce have all snapped up startups in this niche recently. While everyone professes to hate scheduling meetings, many people aren’t willing to remove themselves from the equation entirely, because they fancy themselves kind of good at this game. 

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 among. When the recipient clicks on a time, it’s added to both people’s calendars.

The trick, according to 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.” 

X.ai, which is in a private testing period, isn’t that savvy yet. If Amy approximates a personal assistant, she is that type who is often out to lunch right when you need something done.

The system took so long to schedule a lunch meeting with one of my editors that we had already eaten by the time he received an email. Mortensen says the delay is intentional; right now he’s more concerned with making sure data are collected correctly and accurately than providing a final product. 

The first thought I had when using Amy was: There’s no way I am trusting this computer with every one of my meetings. When my boss’s 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 annoyed with me. But many interactions whizzed along with no problem, often with people unaware they were dealing with a computer. 

I asked Dan 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 organization might feel cold outside that organization,” he says. 

One person who refused to play along was Charlie O’Donnell, a Brooklyn-based venture capitalist. After several attempts to schedule a meeting with O’Donnell, Amy wrote me an apologetic email saying that he wouldn’t respond. So I stepped in, and O’Donnell quickly sent an email directing me to the interactive calendar on his website. The tables had turned. 

 I asked O’Donnell about it when we met up. “I’ll admit it, I purposely ignored it,” he said of Amy’s attempts to schedule a meeting with him. “I felt weird talking to a robot.” I told him I also found it annoying to have to fill out a Web form to meet with him, and he said he heard that often.

But he likes to have a policy that seems to promise to meet with anyone who visits his website. It makes people pitching businesses feel as if they have a chance. “I don’t take any more meetings because of that app,” he says. “But there’s the perception of accessibility.” 

This kind of social maneuvering is a lot for a computer to handle. Mortensen acknowledges that it’s early days for X.ai. He won’t say how many people are using the system, only that Amys and Andrews have scheduled tens of thousands of meetings so far. The company is quadrupling the size of its test group in September. It is planning on a limited commercial launch later this year.  

Over time and with enough users, Mortensen argues, X.ai’s computers will be able to do things that mere humans could never do. Take the issue of serial meeting cancelers.

You might really hate getting stood up for an 8 a.m. coffee but kind of enjoy when your last meeting of the day bails. The problem is that you don’t necessarily know who is most likely to cancel. Amy does. If you tell her not to schedule meetings with unreliable people in the morning, and you are setting up a meeting with someone else who uses Amy, she can show him only afternoon times. Neither human has to know what’s happening. 

“There have to be penalties for flaky people,” says Mortensen. “Today there are none.”