Staying in touch with my team is important. So, I schedule a skip-level meeting with someone on the team each week. These informal conversations are great for getting to know everyone, finding out about new ideas, and learning about recent achievements.

Getting these organized across a couple of dozen people is logistically challenging and I’ve developed a Shortcut to automate most of the process.

Borrowing from Scotty Jackson, I have a base in AirTable with a record for each team member. I use this to store all sorts of useful information about everyone, including when we last had a skip-level meeting. The Shortcut uses this field to pull out team members that I haven’t met with in the past four months and then randomizes the list of names. Then it passes each name over to Fantastical while also incrementing the date by a week. The end result is a recurring set of weekly meetings, randomized across team members.

The hardest part of the Shortcut development was figuring out how to get the names in a random order. A big thank you to sylumer in the Automators forum for pointing out that the Files action can randomly sort any list, not just lists of files.

I’m not sharing the Shortcut here, since the implementation is very specific to my needs. Rather, I’m sharing some of the thinking behind the code, since I think that it demonstrates the general utility of something like Shortcuts for managing routine tasks with just a small amount of upfront effort.