Writing Weekly Updates

I had a former VP of engineering that built a habit of writing a weekly update during his first 90 days on the role. I think there were two main reasons for him to do this:

• Synthesising and communicating learnings.
• Demonstrating activity.

Both are practices of learning & doing in public, rather than behind closed doors. The assumption here is that people in the community you’re serving are invested in your collective success and will help you course-correct to become a better steward.

Personally, I’ve found a written weekly update really helpful when a lot is happening in your environment, in your projects, or for yourself. With a lot of motion, I’ve found it easy to get lost in local swirls and eddies of action and thought and even the power of day-over-day inertia. I’ve also found it a great practical example of mindfulness in the workplace, where it has become a session in gratitude or a moment to reflect and practice awareness.

This is a potent activity for an (onboarding?) leader when a trusting community receives your updates and acts to support you. Your updates need to provide a rudder for course correction: explicit and implicit openings in your updates seeking feedback to correct perspectives, proposed actions, what-have-you. Learning in the open like this also benefits in building stronger communal ties. This approach is beneficial even without sending learnings to the broader world. I strongly recommend pushing for a community to learn with, yet I’ve found much value with myself as the sole audience.

As an individual, the practice is not much different – write your update as before; later, you need to review this as a critical reader to see what can be done differently. It is essential to sequence these items and partitions them as independent activities. I literally have different times to write and read the updates, not for logistical reasons, but to let me entirely adopt the right mindset. When writing, I need to synthesise, demonstrate, and ask for help. When reading, I need to internalise, understand and offer assistance. These are different operating modes for me that need separation in time. Occasionally, I’ll go back and read several updates in a row to understand how my thinking has evolved and what has been implicitly lost to time. I don’t keep a strict schedule for the latter. Still, I have found that this winds up happening 2-3 times a quarter (usually when writing an update and wondering aloud why or how I got here).

When (re-)reading my update, I likely won’t have the answers to my previous self’s calls for help. In a distributed update, there’s an implicit push for feedback. In solo mode, I need to pull in resources. The “reader” headspace helps me put some distance between the person-with-the-problem and think more holistically about how to help. Whom can I tag? Are there resources already? Is there a related domain? When distributing your update, make sure that your recipients can frame and answer the same questions.

I've found the golden rule is to omit status information in writing an update. Updates build upon previous updates, incrementally adding new learnings and areas of uncertainty; a status blurb rarely captures either of these critical facets. The update also needs to make it easy for readers to take action. I try to synthesise my learnings down into a principle and adjoin the requisite facts to support. Ensuring that it speaks very clearly to the strengths of the community I’m addressing also improves callback rates.

I prefer to have my updates as full-fledged written text, not bulleted sentences, phrases or fragments. I write a half-page at most, capturing the critical aspects of what I’ve learnt, implications (to myself, others, projects, org), and where I’m unconfident or uncertain. I don’t layer in links to docs, resources, graphs, or anything else. This structure is low friction for me. I can review my week, jump into a blank page, and start typing productively. You will need to tailor this for the style that works best for you. Just ensure to keep the principles above inviolate.

Even when I have a lot of varied or different projects in flight, I’ve never really had to vary this format. These days, I serve a few distinct communities and am toying with the idea of having a slightly longer, all-encompassing update that I would judiciously edit/synthesise for each community to meet my preferred form. But I haven’t actually done this yet.

I do these updates weekly. Depending on how quickly your environment changes, you may need to vary this. I can’t imagine doing this less frequently than fortnightly, TBH, since in my context, so much can change in that time. Similarly, more often than weekly, it becomes a chore, defeating the point.

“Leader” or not, the practice has been helpful for me. I haven’t been the best at keeping this habit, dropping because of changing priorities or just poor time management. Changing the minimum acceptance criteria when I’m pressed in these situations is really helpful. It can be a permanent change or a temporary one: you pick your adventure. Even with a spotty application, I’ve found it beneficial. It embodies aspects of mindfulness (reflection, gratitude and awareness) and active learning (synthesis, framing and call-for-help). When shared with a community, it helps bring them together through honest, shared, and inherently vulnerable communication focused on a shared experience and outcome. There are so many ways to implement this, but those key aspects really draw me to this practice.