When I started at Zillow, one of the first things that was needed was creating a system of observability and accountability at the team level. What’s the status of that project? Are we prioritizing correctly? What aren’t we doing? These are basic questions that anyone in an organization should be able to answer without needing to ask someone.
I have found three at answers at scale at the company level. This post details these levels of enterprise maturity and gives a starting point to help you grow if you’re starting at the beginning like many are!
Oh Bluehost, how I hate you. I already blogged long ago how I got suckered, but distinguishing my hosting from my blog tech stack is important; they are two separate things!
Recently, my posts weren’t notifying subscribers due to the cron not running. So, I installed WP Control for observability into the system to see what was going on. All this did was confirm that my email notifications from MailPoet weren’t going out. But why? And how did you know this was a cron issue, Straker? Claude!
Last week, I blogged about being a builder and getting your computer setup. But before you go off to the races and start agentic coding, we need to be sure you have a collaboration model setup with your team. Your chat history is stored locally and cannot be viewed by your peers to “keep up.” At the same time, while development may be faster now, producing more features that don’t move the needle and are hard to maintain is an anti-goal; that is how you end up with a confusing product like Jira instead of a product grounded in strategy.
If you want to run fast, run alone. If you want to run far, run together.
Last week, I blogged about PMs becoming “AI builders.” Step 1 to enable this? Getting your local development environment setup. Note that I have completed this both on Windows and Mac. In 2026, with Powershell + IDEs like VSCode, development in Windows is doable! However, Mac & Linux still reign supreme for development; I recommend the switch for this role if you are on Windows today.
Every day, there are new articles sharing that organizational models and ways of working must change in our new AI-enabled world. If this is actually happening, then what does this actually mean or look like in terms of how we work together in the modern era? That’s what this post will explore!
Say it with me: AI is tool, not an outcome. What matters are outcomes.
You know what nobody asked for? More low-quality Product Requirements Documents (PRDs). This is what the slop problem has created though, ironically decreasing overall organizational efficiency for the only thing that matters: speed to delivery. Everyone is so focused on improving their own personal efficiency they’ve lost sight of what matters: the organizational efficiency.
Read the post to avoid common traps and level up your approach to using AI in your daily workflow.
