The Politics of Calendar Bots

Appointment scheduling has always been a power game. Secretaries in Mad Men book meetings as either supplicants or gatekeepers, depending on the ranks of their bosses. In Japan, a surprising number of entrepreneurial success stories begin with begging for an appointment. If you’ve ever had a friend ask you to contact his/her secretary to arrange coffee, you know about the power dynamics of which I speak.

When I first heard about automated online scheduling assistants, I thought they might change all that. After all, these services let you book appointments according to a set of fixed rules, so that should alleviate the power struggle, right?

Wrong.

How Automated Scheduling Assistants Fuel a New Kind of Power Struggle

I first encountered online scheduling assistants about six months ago. I was trying to set up a meeting with a customer, when he sent me a link to his schedule through a service called Calendly. With Calendly (and similar offerings like Vyte and TimeTrade), you specify open blocks of time (say, Tuesdays between 10 am and 11 am) and other constraints (a 15-minute buffer between appointments, etc.), and then you send a link to your invitee, who can book an open slot.

Here’s what the schedule I received from my customer looked like:

I immediately recognized this as brilliant, because it eliminated days of back-and-forth.

However, I was also keenly aware of a dominance-laden subtext: “If you want to meet with me, you will do the work of scanning both of our schedules and choosing a time that works.” Before Calendly, someone might pull a power move by forcing you to go through their assistant; with Calendly, they’re asking you to be their assistant (at least for the part of an assistant’s job that includes booking appointments).

I did want to meet with my customer, so I chose an open slot. I also registered for my own Calendly account. (I have no relationship to Calendly, other than as a paying customer.) Since then, whenever anyone wants a meeting with me, or I want a meeting with anyone, I send them my Calendly link.

The 3 New Calendar-Bot Power Games I’ve Encountered

Having used Calendly for several months now, I’ve noticed that some people love receiving my Calendly link. A venture capitalist I work with, when she wants to meet with me, always asks, “Can you send me that Calendly thingy?”

Others have more of an issue with it. In fact, I’ve so far encountered three new types of power games around Calendly and similar services:

#1: First Mover Advantage: The race to send your booking link

Let’s call him Javier. I used to send Javier my Calendly link to schedule appointments with him, but a few weeks ago, Javier started sending me his Calendly link first, forcing me to do the booking. Now, whenever we want to get together, I feel pressure to send him my Calendly link first, so that he has to do the booking.

#2: Battle of the Bots: Calendly vs. Amy

One man responded to my Calendly link by forwarding it to “Amy,” an automated scheduling bot from a company called X.ai. After that, I got emails from Amy proposing times to meet, not only completely ignoring my Calendly openings, but also asking me to email with what was obviously a computer program. I was so annoyed that I ignored Amy’s requests until the man reached out and proposed times himself.

#3: Power Penance: Booking as apology

I’ll call this person Richard (because that’s his name). I lost to Richard in game #1: he was quicker on the draw with his TimeTrade link than I was with my Calendly one. His TimeTrade calendar had very limited openings, though (which I should probably have listed here as Calendar-Bot Power Game #4: Ridiculously Few Slots), so I had to book an appointment several weeks out. When the time came, I called him (Calendar-Bot Power Game #5: Make the Person Who Books Call You), but he didn’t answer. He emailed a few days later with a (dubious) excuse about being out of cell range, and proposed a time to reschedule. I couldn’t make that time, but it provided me an opening to send my Calendly link, which put the scheduling onus (and dialing duties) back on him.

In Case I’m Not the Only One This Sensitive to These Power Dynamics

The unbelievable amount of time that Calendly saves me when scheduling meetings makes it my favorite productivity tool, bar none.

That said, I always accompany my Calendly link with words to this effect:

The easiest way to schedule a call is to choose a time that works for you here (but if none do, or if you prefer, just email me some times and we’ll schedule manually).

Or sometimes, like Taylor McKnight, I just refrain from Calendly entirely. That way, if others are as sensitive as (apparently) I am to the power dynamics of automated scheduling assistants, we can always go back to good ol’ “Do you have any time next Friday?”