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The Slide

The single biggest challenge for new managers — giving up the responsibility for the product… for the building. Learning how to give accountability for projects of significance to the team. It’s an essential set of complex skills involving trust, communication, and, most importantly, judgment. Failure to understand delegation is failing to be a leader. Senior or not.

— Michael Lopp, The Slide

AI Prototyping Is Changing How We Build Products at Uber

There is no doubt that this post was at least 80% written by AI but I’m not even super mad about it because that is just the way of the world now, and the summary it generated from how Uber works is actually legit interesting:

A prototype without a PRD can drift away from the problem the team intends to solve. A PRD without a prototype can remain abstract, leaving room for inconsistent interpretations. […] If going from idea to prototype is now fast and cheap, the PRD can no longer be the primary place where ideas are defined. Its value increasingly lies in capturing intent, tradeoffs, success metrics, and decisions.

The PRD as an artifact is in the spotlight right now in a way that I think is really healthy. Should it remain but change its JTBD? Should it be an eval instead? Who knows. Let’s figure it out together…

Release: tldl v2.3.0 — Email subscriptions

Project
TL;DL
Summary
Your favorite podcasts, summarized.
URL
tldl-pod.com

Per-podcast email subscriptions for tldl. Pick the shows you care about at /subscribe and the summary lands in your inbox as soon as a new episode is out.

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Org Design in the Age of AI

This post on org design really resonated.

Most companies today are using AI the way you’d use a faster horse — to make the existing structure run a little better. The companies that pull ahead will be the ones willing to ask a harder question: what would we build if we were designing this organization from scratch, today, knowing what AI can do?

We have to seriously rethink the SDLC, design it from scratch in the context of how our own organizations work. It’s not about a global “right” process any more. The question now becomes “How can the humans in our team, at our company, at this point in time, work best together to serve our customers?”

The peril of laziness lost

Oh, this is very good. On the classic take that the core characteristic of outstanding engineers is “laziness”:

The problem is that LLMs inherently lack the virtue of laziness. Work costs nothing to an LLM. LLMs do not feel a need to optimize for their own (or anyone’s) future time, and will happily dump more and more onto a layercake of garbage. Left unchecked, LLMs will make systems larger, not better — appealing to perverse vanity metrics, perhaps, but at the cost of everything that matters. As such, LLMs highlight how essential our human laziness is: our finite time forces us to develop crisp abstractions in part because we don’t want to waste our (human!) time on the consequences of clunky ones.

The best engineering is always borne of constraints, and the constraint of our time places limits on the cognitive load of the system that we’re willing to accept. This is what drives us to make the system simpler, despite its essential complexity.

This is exactly why I practice Fear-Driven Development, and why everything I do in code includes multiple versions of asking Claude Code “do we need this?” and “is this adding bloat?”

Two small new things on the blog

Now that the site is off WordPress, I can finally start doing a bunch of things I’ve wanted to do for years. Here are the first two:

1. Auto-posting side-project releases

When I tag a GitHub release on one of my side projects — tldl, listentomore, discogs-mcp, and others — a post now appears on this site automatically. Title, tagline, release notes, and a link back to the GitHub release.

I ship a lot of small improvements, and historically none of that work was visible anywhere except the GitHub tab nobody reads. Now it shows up on the blog as a first-class content type.

2. Per-content-type RSS feeds

If you only want the long essays and not my link posts or quotes about other people’s writing (or the release notes, for that matter), you can now subscribe to just those. There are six feeds:

I’ve also updated /subscribe with the full list. And a reminder that RSS is very much alive and well. Get started with What is a Feed?.

Release: discogs-mcp v3.2.0 — Catalog-wide search

Project
discogs-mcp
Summary
Discogs MCP server.
URL
github.com/rianvdm/discogs-mcp

Adds search_discogs for catalog-wide queries beyond your own collection, plus two real-world accuracy fixes: owned-marker correctness across pressings, and exact genre/style matching.

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Release: tldl v2.2.0 — RSS-first monitoring and audio-URL dedup

Project
TL;DL
Summary
Your favorite podcasts, summarized.
URL
tldl-pod.com

Two meaningful changes since v2.1.0. tldl now detects new podcast episodes directly from RSS feeds with conditional GETs instead of relying on Podcast Index re-crawls, so episodes typically land in the queue within minutes of publication. A second fix catches episodes that get retitled or have their GUIDs regenerated after publication — a surprisingly common pattern in the wild.

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What actually changed about being a PM

I have decided that in this new AI era I will be practicing FDD. Fear-Driven Development. Every time I send a pull request, which happens a lot now, I'm terrified of an engineer sending it back to me and asking me to please stay in my lane and stop sending them slop. So I plan, write specs and implementation plans, test thoroughly, and I don't trust the agent's inevitable confidence.

I'll come back to that, but let me first frame what this post is about. The loudest take on PM work right now is that AI is collapsing the role — that we're one product cycle away from redundancy, or being reduced to prompt jockeys. That hasn't been my experience at all. The job got more hands-on, harder (brain fry is real), but also a lot more fun. What follows is what actually shifted for me over the last 5 months at Cloudflare, what didn't, and a couple of things I got wrong.

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Stand out of our Light

It’s my firm conviction, now more than ever, that the degree to which we are able and willing to struggle for ownership of our attention is the degree to which we are free.

– James Williams, Stand out of our Light: Freedom and Resistance in the Attention Economy