How to send progress updates

Writing good progress updates is an art. Many people (myself included) treat them as a "what we've done" roundup at a regular cadence. This makes the updates boring to write, and boring to read.

Instead, treat the updates as a deliverable target:

Know what your next update will be and work toward it (instead of coming up with an update when it’s time to send one). This is Headline driven development for an internal audience. If you don’t have a headline you don’t have an update, and you can’t generate good headlines post-factum.

The people reading your updates don't have much time, and are juggling so many things they're likely also lacking context too:

Always start with a one sentence TL;DR and a 2-4 sentence recap of the overall goals of the project. Assume your audience is smarter than you are, but is very busy and remembers nothing about your work.