My scheduling bot’s failure restored my faith in humanity

This is not the bot in question.
This is not the bot in question.
Image: Reuters/Benoit Tessier
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It’s hard to go a day without reading about artificial intelligence. Bots, machine learning, algorithms. It’s terrifying to think how many jobs will be lost. I try to speak with a human whenever given the choice. I seek out a waitress so I don’t have to order meals over an iPad. I’d rather wait on a line for a cashier than swipe my purchases over a scanner.

Even so, despite my high minded principles, scheduling meetings is such torture that I could not resist trying a bot.

Most tempting was the thought of liberating myself from endless email chains when trying to gather a group with everyone weighing in and no one bothering to read to the bottom of the chain so that invariably, after 20 emails, someone proposes the date and time that has been rejected in the first email. In the old days it was easy to remember phone numbers of friends. Now I have to remember whether each one uses Facebook, text, Twitter, Whatsapp or Instagram. Paperless Post, Slack and Doodle. Worst of all is the rescheduling: people feel free to change plans, even at the last minute. Some days a third of my meetings never materialize, setting off a new round of scheduling when the people who cancelled decide they need to meet after all.

Making appointments should be easy to automate so I asked around and was told about Clara Lebesgue, a bot cleverly named after a 19th century French mathematician. For a mere $99 a month, all I had to do was hand over my passwords and Clara, supported by a real person, could be cc’d on my emails, get to know my preferences and would manage my calendar while I got on with more interesting projects.

I wasn’t sure how my friends would feel about being scheduled by a bot so in the beginning I only used her on volunteers and I let people know she was a bot. Even so, everyone thought she was a real person.

Right away she annoyed me as a real person might. Her perky informality got on my nerves. She began all emails, even work ones sent to people we didn’t know, with the word “Hi”. She used copious exclamation points. She cc’ed everyone in cases when a more discreet direct reply would be more appropriate. In an attempt to train her, I asked nicely at first and then became terse.

Dear Clara, No need to cc everyone. You can call him Mr. G____ and his wife is Ms. B____. Thanks a lot.

Please stop with the exclamation points.  Thanks very much,


She replied with meaningless office-speak.

Hi Anya,

Thank you for reaching out. Please know that I need to CC everyone in my scheduling process in order to gather their information, unless I am scheduling with a designated coordinator for them. Also, eliminating exclamation points altogether is not something that I can reliably support.

Happy to loop in Customer Support for further assistance.



Worst of all, when I did hear from a live person from Customer Support (suspiciously all had names like “Trina” and profile photos of pert, young, blondes) I was told that my personal bot was not trainable. This unwelcome news was conveyed in a message that included yet another unnecessary exclamation point.

Hi Anya,

We really appreciate you taking the time to send along this valuable feedback!

While Clara’s verbiage is not yet customizable, I do see how these changes could allow Clara to be used more universally. I’ve passed your suggestion along to our product team in hopes this can be included in a future release.

If there’s anything else we can do to help, please let us know.


Customer Success Specialist
Clara Labs

Ambiguity was beyond Clara. I noted in my calendar that my niece was coming to New York for the summer and Clara was then thrown into a state of paralysis as she thought she couldn’t schedule any appointments during the entire visit.

Nor could Clara grasp the nuances of human language. I got an email from someone I had never met asking to see me and I replied something like “would love to meet but I am flying that night and will be away for six weeks.” A human being would have understood that I was saying “please go away.” Instead, Clara blithely scheduled the meeting at home and so the poor woman arrived to find me surrounded by suitcases and coincidentally (not Clara’s fault) during a flash flood. Luckily she laughed when I explained that it was a bot scheduling glitch, drank a cup of tea and then insisted on leaving despite the driving rain.

Clara’s modus operandi was to ping everyone I know all the time, bug them to set up a date and then send them endless reminders or emails asking for clarifications. I lived peacefully, blissfully unaware of the spam she was sending out.

The final straw came when Clara offended someone I didn’t know well. I had tried to explain that meetings in my office could be 30 minutes but that when I go out for lunch I want to spend at least an hour with whoever I am seeing. Clara had a hard time absorbing this and started scheduling short lunches at the other end of the city. She did this to a work acquaintance who had just been fired and who I had invited to lunch so as to cheer him up. He sent a polite note asking why we were only meeting for 35 minutes.

I happily threw my bot under the bus for this gaffe, though I gave her three weeks notice, just like a real person.

The good news is that we may not have to worry about automation taking away all the jobs just yet. “Clara is enough to restore one’s faith in humanity,” my husband concluded.

By this time Clara had become a conversation piece and the subject of multiple Facebook posts. I began to feel guilty about mocking her. Was I becoming like one of those women in old novels who complained about the “servant problem” ? What are the ethics of mocking an incompetent bot?

Again, I thought back to New York in the seventies when one would phone a friend, date book in hand, agree on a meeting place and that would be that. We’d meet on a park bench or a bookshop so if one person was late the other would not be left standing outside. If a friend was 20 minutes late that meant the plan was cancelled and one would leave without hard feelings because the afternoon had not been ruined. In Spain, where my mother was born and where I spent summers, some people still practiced the old habit of going to the same place at the same time each week. My great aunt Carmen in Madrid could be found at Casa Polli every Wednesday at 3 pm eating roast chicken for lunch and being waited on by Alvaro. In Barcelona, Gonzalo Herralde went to the same bar every Friday before dinner. If one wanted to see him, one went there.

Even so, I wasn’t ready to give up on the idea of outsourcing my scheduling to a bot. I went online and found Finn, who claimed he could learn my favorite restaurants, preferences and habits. Unlike Clara he would be able to make reservations and order flowers, all for $1 a minute. I started off by asking him to find me a very quiet restaurant in London within 10 minutes walking distance of my hotel because I was inviting a widowed octogenarian to dinner and wanted an evening of quiet conversation. Finn blithely wrote back to say he’d a booked a place “but I cannot guarantee a super quiet atmosphere. After all, this is the heart of London and it’s buzzing at night!”

The bill for his time: $150.

I fired Finn, too.

Unsurprisingly, many have reverted to the old habit of having an assistant do their scheduling, thereby undoing the whole point of the Internet—the disintermediation and the egalitarian spirit that digital technology was supposed to bring to the world.

I can’t go back to the days of simply picking a park bench at an agreed-upon time, but after my dalliances with bots I, too, decided to go back to using a real person for scheduling. Hannah is smart, empathetic, discreet, and understands that I don’t need reminders telling me how long it takes to walk to my office. She’s more expensive than a bot because real people have to pay taxes, contribute to social security, buy health insurance and repay college loans. But I wouldn’t have it any other way.