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Thematic Meeting Days

During my time at Square, I got to observe Jack Dorsey as he figured out how to scale himself out to first one, then two fairly large enterprises. His pennant for media attention in those early days—particularly since he started re-engaging with his first company, Twitter—was more hype and distraction than I think was beneficial to the companies. But, one idea he introduced was the idea of having themes for each workday, to great fanfare and admiration.

It’s a simple and semi-structured scheduling strategy which I’ve wanted to give a fair shot since learning about its utility. With a growing team and a glut of meetings recently, however—once I got past the smug sense of feeling busy, I’m actively blocking out hours on my work calendar to tetris my schedule, to limited success. I’m appreciating the reality that at a certain point, the exercise of maintaining and updating a calendar full of events is non-trivial at best; cascading failure can apply to meetings as much as it does to interdependent software systems1.

In response, I’ve been trying to loosely organize my own schedule around themes. There is just too many instances of random noise and “things that have to be done” throughout the day that make strict adherence possible, but I have come to a system which tries to impose some structure on a manager’s schedule. It looks something like this:

Monday is for cross-functional meetings. In my case, since I manage engineers and engineering managers in a product-focused organization, I end up meeting with designers, product managers, and recruiters. Mondays are a double-edged sword: energies are generally higher coming into a new workweek and planning pays off the most up front, but there are enough instances of long weekends which adds some amount of uncertainty and inconsistency.

Tuesday is getting aligned within the functional organization, and is the most important day for meetings. I have a number of engineering leads meetings reoccurring every Tuesday, along with 1-on-1s with my own staff engineers and managers. If Monday is more about easing back into work, Tuesday is the intense follow-up, and so I try to reserve it for the most important communications.

Wednesday is a good day to think about engineering. If I have meetings, they’re with other engineering leads across the company, to sync up on new and ongoing technical projects. Wednesdays are also reserved for a rotating set of org-wide all-hands centered on engineering topics in the form of tech talks and open Q&As. If I have extra time, I use this day to read through and comment on technical specs: the timing allows some buffer to opine on documentation shared from early in the week, while responses and follow-through carries through the latter half of the same week.

Thursday is about people. I try to schedule the rest of my 1-on-1s here, particularly with my non-manager direct reports. As I’m getting used to this schedule, I’m starting to squeeze in skip-level 1-on-1 meetings on Thursdays as well, though it’s been difficult to fit everyone in as we scale the team out2.

Friday is for meeting overflows and actually getting work done. Like Mondays, a lighter load allows for more flexibility into the weekend.

And that’s the gist of the scheme. Granted, the cost of context switching isn’t as prevalent when it comes to dealing with meetings3, so this is more about ensuring enough space is allocated per thematic area, and optimizing against gaps in managerial coverage.

Now I just need to figure out how to carve out time to think.

  1. Incidentally, I am starting to see the roles that executive assistants play, though their work is primarily in support of C-level folks above me.

  2. At one point, Jack Dorsey promised that he’d do walking 1-on-1s with every employee at Square and would get to everyone eventually. After 5–6 or so of these, he realized that the number of hires and starts outpaced his ability to conduct these conversations, and promptly gave up on the idea.

  3. At best, there are a handful of instances where talking through some recent event with reports all on the same day would be considered batching.

By allen
allenc allencheung