What Calendly Is Teaching Me About AI, Or Why I Still Believe in Free Will | First Avenue Ventures
Years, maybe decades, ago, I had a discussion with an executive about whether or not you should have an assistant manage your calendar. The argument in favor went something like this: scheduling meetings takes time and your time is precious; delegate it down to save time and money. Additionally, having a gatekeeper saved you from having to say no to someone with whom it would be a waste of time to meet — again saving time and thus money.
While these are some very valid points, I did (and still do) disagree. Too many variables enter into the equation: when and where to meet someone, how to prioritize meetings, how to determine if it’s a meeting to put off or take immediately. How you spend your time seems very personal, and delegating it seems fraught with danger.
Now, we have Calendly. An app I personally do not use but am seeing people use more and more, which is fine. I don’t really have a strong for or against opinion on it. However, I do see two issues with the app. First, I’ve seen some people complain about their schedules being filled with Zoom meetings, and I can’t help but wonder if that is the Calendly app running wild. You have seven spaces on Wednesday; it fills them all as you gleefully cut through email scheduling. Secondly, we haven’t yet developed an etiquette around when and how you roll out the Calendly link. I recently saw a discussion about this on LinkedIn; it was long and nuanced, but ultimately inconclusive.
So it seems like the more things change, the more things stay the same. With Calendly, you can schedule things more quickly. Administrators are probably eased of another burden and of endless emails. But the app still doesn’t know if the user wants the meeting or not, or when they want to meet, or how; it’s entirely dependent on past user behavior and binary choices. While I expect that these issues will evolve, technology will never completely replace the human element of calendar management, which is, after all, how we choose to define how we live.
Parallels exist here between this trend and the larger disruption caused by tech. And the calendar management app causes disruption for sure: if your sole job is managing your boss’ calendar, I would be worried for your long-term job prospects. And personally, I love the efficiency gained from not having to go back and forth over email. At some point, I’m sure I will use it myself.
But there is always going to be a limit as to how much I turn this over to someone else — human or machine. Only I can know the nuances, so I’ll use it in a limited way and not simply turn it over wholesale, no matter how convenient it is. No one but me knows how to fill my professional work time and I think that’s probably a good rule of thumb in general.
Also, I think other areas exist where you hit the limits of tech/AI. Several years ago, I thought the LinkedIn algorithm produced great insights. But now, over time, people have juiced the algorithm and it produces a crummy feed again. Just like a calendar, my feed is a matter of taste. Maybe — actually, hopefully — they will get better, but I think it’s going to require human curation for a long while (Am I reading something because I agree with it or am I reading something because I want to be illuminated on arguments with which I disagree? At this point in tech, only I know).
So while technologists can and will tell me I’m wrong and fret over the ubiquity of AI in the world to come, I remain optimistic that tools will help us be better people but not make us less than people. Algorithms can only produce a sum of our prior experiences. They cannot determine taste, preference, and the randomness I bring to both. My free will cannot make me a slave to the machine. The future is still for us to decide.
Originally published at https://firstavenueventures.com on October 23, 2020.
