The Pitfalls of Appointment Scheduling Software


The goal of appointment scheduling software - Acuity, Calendy, HubSpot, etc. - is a noble one. No more back-and-forth emails trying to pin down a meeting time.


I love it when people let me see their availability and pick the day and time that works best for me. But I rarely use this software for my own meeting invitations.


If time is money, then pinning down a meeting time is a negotiation. If someone lets me pick my ideal time, I win, because I get to pick the time that perfectly aligns with my productivity cadence.

I have a few standing meetings that appear every week or two. My goal is to only schedule ad-hoc meetings that are immediately before or after those regularly scheduled meetings. In effect, what I’m creating is a window of time where I’m in “talking mode” over the course of several meetings.


Having random meetings across the day is distracting, it leads to energy depletion, and it makes it harder to get into a state of flow. I take this to the extreme and try and create talking days for teaching and meetings, and non-talking days for deep thinking tasks like writing and analyzing data.


Scheduling software is amazing, but to my knowledge, none of them are smart enough to accommodate the level of customization necessary to ensure that my days are scheduled the way I want them to be scheduled.


I’m fine with a few back-and-forth emails. The cost of those few minutes pails in comparison to the cost of distractions.

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