Better time-leverage

I’ve started using Calendly to help manage my calendar & appointments. Right now, I’m using it bare-bones at the moment, to see if it works for me, because of a singular problem with all of these calendaring-automation tools that I haven’t figured out yet:

It feels dangerously self-important to ask people to schedule their own appointments with me.

I’ve always prided myself on my “human connection” skills within the tech industry, and the UI for all of the various calendaring apps still, in my opinion, feel like bots, not like assistants. Additionally, many feel like they want me to run my calendar in their UI, not work alongside my existing workflow.

Anyway — that’s just really an aside about the point of this post. Being a one-man-shop freelancer/consultant, time management is super-important. I’m also hyper-aware of how easy it is for a single meeting to run roughshod over an entire day’s worth of tasks, depending on its cognitive or emotional load. And so, when I book a meeting, I often then look to be most efficient by having other, adjacent meetings — a day of meetings feels productive. A day with a meeting, then an hour of heads-down time, then another meeting often feels like it was totally wasted.

Calendly, which offers a “buffer” around meetings, which is great — but doesn’t appear to offer any location data — which is important to me because I often (and indeed, usually prefer) in-person meetings. Which involves travel. So, if when booking an appointment, Calendly could ask for a where, then use my office location to calculate travel times, add that to *my* calendar time and buffer around that meeting, it would become vastly more useful.

But once I’m in a location, it would be great if I could schedule other meetings nearby:

  • On a hyper-local level, if I’m having a coffee meeting in Gastown, it would awesome if Calendly connected to my CRM of choice, and see which contacts are near my scheduled meeting (ie, also in Gastown), that I haven’t seen in a while, and send me a note letting me know it might be a good idea to try to connect with them.
  • On a regional/travel level, if I’ve got an upcoming calendar trip to, say, Toronto, check my CRM to see who might be available while I’m there to meet with, and suggest it to me. (next level: find people I don’t know, but suggest I should try to meet them)
  • aside: this is a problem with calendaring I don’t have a good answer for: When I’m away, I generally mark that time in my calendar as “busy”, because I don’t want anyone here to book time with me. but, I might totally want to book time with people there. I want a “busy-in-location” marker, or a “location change” marker to connote travel vs just being busy.

I recognize there’s a lot of data mining/analysis going on there. And, most likely, that’s a service that shouldn’t be provided by Calendly, but rather integrate via API (although, I do think not supporting location/travel time is a big problem for Calendly at the moment). And possibly there’s already services that sit between these data-stores to do just this task that I’m unaware of. And that’s also, personally, an area of interest — software tools that work with existing data-stores for people to help tie them together in interesting ways, and surface helpful things for you, so I think a lot about pulling data out of silos and tying it together.