The Politics of Calendar Bots
How scheduling apps create new power games
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 your contacts book appointments quickly and easily, so that should alleviate the power struggle, right?
How Automated Scheduling Assistants Fuel a New Kind of Power Struggle
I first encountered online scheduling assistants six months ago. A customer sent me a link to book time with him 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 (always leave a 15-minute buffer between my appointments, for example).
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.
But 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.
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 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 him my Calendly link to schedule appointments, but a few weeks ago, Javier started sending me his Calendly link, forcing me to do the booking. Now, whenever we want to get together, I feel like it’s a race to send the Calendly link first so the other person has to do the work.
#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 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: Limit How Many Slots You Offer To You Seem Busier Than You Are), so I had to book an appointment several weeks out.
When the time for our meeting came, I called him according to the instruction in his invite (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 with an opening to send my Calendly link, which put the scheduling onus (and dialing duties) back on him!
Advice for Alleviating the Power Struggle
The unbelievable amount of time that Calendly saves me when scheduling meetings makes it my most valuable productivity tool, bar none. It literally saves me hundreds of hours and thousands of dollars a year.
That said, I’ve learned to always introduce my Calendly link with words to this effect, which let the other person propose meeting times instead:
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 I’ll do my best to accommodate).
Basically, I’m saying, “If you want to go back to the old fashioned way, where you’re in charge and we email each other back and forth for days, I’m OK with that.”
In other words, it lets the invitee share in the decision to save time in exchange for giving up a little power, rather than having it forced on them.
In my experience, everyone takes that deal.
