Until this point in my reporting, I’d been on the receiving end of the Ingrams’ overtures, but not a user myself. The time had come for me to sign up for an Amy or Andrew of my own. To give myself a basis for comparison, I decided to attempt to schedule meetings using both X.ai and one of its competitors, Clara Labs. Launched nearly three years ago, in the same month as X.ai, it is one of the human-­machine hybrid services that Mortensen was trying to undersell and out-­innovate. Clara’s approach is known as “human in the loop”—the idea being that humans add value that no machine could ever reproduce. In fact, its founders reject Mortensen’s “fully automated” dream so completely that they put the difference into their scheduling assistant’s first hello: I’m Clara, your human-in-the-loop assistant.

I join X.ai first. The response comes a few minutes later:

Hi John,

I’m Amy and, starting today, I’m your personal scheduling assistant.

All you need to do is CC me (amy@x.ai) when you’d like to schedule a meeting, and I’ll take over the tedious email ping pong from there.

To get started, she suggests I connect her to my calendar and enter my address and my meeting preferences—time of day, favorite coffee shop, etc. She ends the lesson with a cheery sign-off: Always at your service, Amy Ingram :).

Time to set up my first meeting! I send an invitation to an editor, cc’ing Amy as instructed, testing her with a vague proposition about getting together. “I’m going down to Union Square on Friday for a 2 pm meeting, thought we could do coffee or lunch before—maybe 12 or something?”

Things get complicated quickly, and somehow Amy ends up proposing to my editor that I meet him at his home. Because I’m bcc’d on her emails with him, I see the mistake right away and jump in to correct her.

I sign up for Clara and try a similarly vague message. But instead of engaging in needless back and forth, she responds to me directly right away:

Kindly let me know the exact address of where you’d like to meet.

Tech Giants Want to Chat How the Big Five are faring in the race to build the best conversational interface.

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By Saraswati Rathod Amazon Amazon has partnered with manufacturers like Toyota and Sony to incorporate its AI interface in their devices. Meanwhile, the company is hosting a $3.5 million competition to build a bot that can successfully engage in idle chitchat. Apple Siri, the most widely recognized virtual assistant, is now also running Apple’s HomePod. Over the past few years, Apple has been reworking Siri so that it not only responds to your needs, it anticipates them. Facebook Facebook users can order flowers or schedule a ride-share by pinging a bot on Messenger. But not every launch has gone so smoothly. Earlier this year, the company shuttered M, its part-AI personal assistant, because it required too much human intervention. Google Armed with its database of search results, Google Home is six times more likely than Amazon Alexa to provide an answer to random questions, according to digital marketing agency 360i. But while Google may slay at trivia, the two companies are still racing to integrate into TVs and cars. Microsoft Microsoft’s chatbot, Zo, can hold lengthy conversations and play games with users. That tech helped Microsoft develop and improve Cortana, its personal AI assistant, which sends users friendly reminders about promises made in previous emails.

To learn more about Clara—which charges customers anywhere from $99 a month for the Essential package, which includes scheduling 35 meetings, to $399 for the Executive package, with 110 meetings—I call the company’s founders, Maran Nelson and Michael Akilian. In 2014, Nelson was sitting in a San Francisco coffee shop with Akilian, her best friend from high school, telling him about her plan to gather people who were interested in technology and social problems into some kind of think tank. She’d been putting out hundreds of calls and emails to invite people to interview, and as Akilian remembers it, “Her email inbox was totally overwhelmed and overflowing. She was trying to schedule all these people and she said, ‘I wish there was something where I could just say, “Hey, I want to talk to these 50 people in the next three weeks for 30 minutes each,” and that’s it, it’s on the calendar.’ ”

Like Mortensen, Nelson and Akilian set out to program response templates and keyword recognition. But they didn’t try to raise $30 million and spend three years on natural language R&D. “Intelligent interfaces have been the fetish of the entire Silicon Valley community since its inception,” Nelson says. “But natural language processing is really far off, so we conceived of ‘human in the loop.’ ”

That’s where the Clara remote assistants come in. When the Clara AI has a high degree of confidence in its proposed response, it can send the email without bothering a human. But in all other cases, the AI sends the text in question to a CRA like Cat Moore, a 28-year-old neuroscience student from Georgia who works from home. “The first thing we do is read the whole email for context to have an idea about what’s been going on,” she explains. Complications arise with requests like big meetings for 10 people. Those emails can take her 10 minutes to figure out.

Sometimes she customizes the response template a little to add a human touch. It doesn’t seem right to respond to “I can’t make it to the meeting because I was just in a car accident” with “No problem! When do you want to reschedule?” Sometimes the emails say “Sorry, can’t do it, my father died.” That gave Clara’s engineers the idea for an “empathy cues” project. Soon the CRAs had new templates with human touches like “I’m so sorry for your loss.”

“Some things are easier to automate, and some are much harder,” says Jason Laska, who runs Clara’s machine-learning program. “And sometimes you really need a person to do it.”

When I was responding to a message from Clara, I knew there was a human on the other end, so I always started out with “Hi Clara” and thanked her when I was done. But after my first few turns with fully automated Amy, I felt stupid for exchanging pleasantries with a machine and sent back cold and mechanical responses. I couldn’t help wondering: Does talking to a machine make you act like a machine?