Death by a Thousand Comments — Royal Icing

Death by a Thousand Comments<br>June 22, 2026<br>Gergely Orosz of the Pragmatic Engineer newsletter/podcast writes:

I’m seeing so many VC-funded, internally built infrastructure and bootstrapped solutions around “building a context layer for engineering teams.” Aka trying to solve the problem of “if only eg Claude Code had the context from all your other systems”

I believe the “context layer for engineering teams” is called leadership with clear communication.

We have turned everything into dozens of tabs with information scattered across countless clouds which leads to fragmented communication and noisy decision making and so we search for the silver bullet that will make sense of it all.

Perhaps being able to comment on the Figma design and the GitHub pull request and within the last Slack message and on the issue tracker and within the monitoring system is making our communication worse not better because our brains have to literally tie it all together into a consistent model.

You chat to the same coworker in dozens of places. Imagine being in an office and having a conversation with someone and then having to switch rooms every time the topic changed? “Yes this code is a little odd (walks into the GitHub room) but if you read our plan (steps into Notion) then it’s clear that this database decision requires us to do this (points at Alex’s comment in Notion) and it was constrained by what we have in the designs (enters the Figma chamber) which you can see the client approved last year (strides over to Slack where furious searching for the message is conducted).

If you see the old hats at Apple and Microsoft they loved email. I don’t but I’ve begun to understand why they liked it. They spoke in the most straight-forward way with single sentences going back-and-forth and missing punctuation but the message was clear! They didn’t need to dress it up with formalities and executive summaries and TLDR sections and hastly-assembled tables and diagrams that are now so out of date so you ignore them anyway.

Single-sign on has encouraged us to set up many mini-offices with their own communication channels. But it’s with the same folks! So then there’s 11 versions of “Simon” that you have to piece together like Poirot the detective trying to understand the killer’s movements in the final hours. Simon posted here 15 minutes ago but then commented here before but this message came later with a link to this issue here where he must have clicked these three buttons that made the build pipeline retry. Which must mean the original message has been resolved! But there’s one comment elsewhere from Jordan that everyone missed and then three new notifications come through…

You chat around the water cooler but there’s dozens of them and you have to work out “are we chatting around this one now or are we moving to this one over here?” like some sort of fast-paced walking tour and you enter a Zoom meeting and see someone else’s view of the same chaos with a hundred pinned tabs like two paintings of the same battle from two viewpoints that capture the drama in markedly different light. And then as the presenter scrolls through you say “I don’t have access to that Google Doc” and then they apologize and someone else half asleep peeps up “me too!” and then finally you hope you have all the pieces to the lego set you just wish you could see the picture on the box that shows what it’s supposed to look like when it’s all put together.

Then as you wait patiently for the invitation email you get pinged about two pull requests that need your re-review and then you hunt down the important conversation that occurred in Slack when the first (or was it the second) PR was posted on Slack yesterday.

So I understand why there’s a desire for an all seeing eye of Sauron scouring the lands of Middle Earth picking up every stray word from every hobbit and piecing it together into a coherent timeline. “Did Gandalf say ‘Fly you fools’ or Flee you fools’” you type into the latest search box that promises to index everything so you never have to go hunting for knowledge again.

Perhaps breaking everything in our organization into distinct proprietary clouds clouded our thinking and crumbled our communication which ultimately hurts our decision making. An organization is supposed to organize a group of people into executing a common goal but we decided as a tech industry the best way to do this is to create dozens of denormalized databases each with their own subset of the data synced sporadically over a network with code you can’t control that each person makes their own eventually-consistent consensus from via fine-grained trust-no-one permission systems that would make Ivan the Terrible blush.

Meanwhile Steve Jobs used Apple fucking Mail to direct the creation of the iPhone. He got context from talking with people and shared context by telling others. He had a regular morning Monday meeting where...