Software Lead Weekly
Issue #705, 29th May 2026
This Week's Favorite
Learning on the Shop Floor
7 minutes read.
Tobi Lutke (Shopify CEO) shares why thinking of intercations and product design as a multiplayer game is so powerful: "When I think about why this matters, it comes back to something I have believed for a long time: the speed of an organization is determined by the speed of its lowest-bandwidth communication channel and rhythm. Meetings are slow. Email is slow. Private DMs are slow. Maybe not for the individuals involved in them, but for the organization. The information and decisions that come from them never fully diffuse into the rest of the organization without huge additional communication effort. A public conversation between humans or with a competent agent is none of those things. It is fast, it is searchable, it is teachable, and it compounds. The next person who has the same question does not have to ask it."
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7 minutes read.
Tobi Lutke (Shopify CEO) shares why thinking of intercations and product design as a multiplayer game is so powerful: "When I think about why this matters, it comes back to something I have believed for a long time: the speed of an organization is determined by the speed of its lowest-bandwidth communication channel and rhythm. Meetings are slow. Email is slow. Private DMs are slow. Maybe not for the individuals involved in them, but for the organization. The information and decisions that come from them never fully diffuse into the rest of the organization without huge additional communication effort. A public conversation between humans or with a competent agent is none of those things. It is fast, it is searchable, it is teachable, and it compounds. The next person who has the same question does not have to ask it."
Read it later via Instapaper.
Share it via Twitter or email.
Culture
Me Using Claude Opus 4.7 to Center a Div
1 minutes read.
My humble effort to help you start the weekend with a smile. Also true for Opus 4.8.
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1 minutes read.
My humble effort to help you start the weekend with a smile. Also true for Opus 4.8.
Read it later via Instapaper.
Share it via Twitter or email.
Software After AI
5 minutes read.
The 7 parts of harnessing the power of Agentic Development, or "domestication" as Tomasz Tunguz calls it, can provide a useful framework for assessing your company's infrastructure readiness.
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5 minutes read.
The 7 parts of harnessing the power of Agentic Development, or "domestication" as Tomasz Tunguz calls it, can provide a useful framework for assessing your company's infrastructure readiness.
Read it later via Instapaper.
Share it via Twitter or email.
Avoiding Death on the Yellow Brick Road: Why the App Layer Isn't Dead
9 minutes read.
The world (as the universe) is expanding, and with that the product(s) surface area needed. I don't think there is a simple zero-sum game where the frontier labs will win the entire ecosystem (please don't throw AGI at me; another term so poorly defined to create mostly drama and inflate valuation). Leaning on complex problems that require tribal knowledge (data extraction and development) and deep expertise (taste, guardrails) can lead to a moat with healthy business metrics in terms of growth and margins.
Read it later via Instapaper.
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9 minutes read.
The world (as the universe) is expanding, and with that the product(s) surface area needed. I don't think there is a simple zero-sum game where the frontier labs will win the entire ecosystem (please don't throw AGI at me; another term so poorly defined to create mostly drama and inflate valuation). Leaning on complex problems that require tribal knowledge (data extraction and development) and deep expertise (taste, guardrails) can lead to a moat with healthy business metrics in terms of growth and margins.
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LLM Oriented Engineering
6 minutes read.
Yair Weinberger shares interesting insights into org design with LLM. I found his take on "Padded rooms: where to let the LLM loose" useful for architecting experiments or branches of customization while controlling risk.
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6 minutes read.
Yair Weinberger shares interesting insights into org design with LLM. I found his take on "Padded rooms: where to let the LLM loose" useful for architecting experiments or branches of customization while controlling risk.
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
Interviewing in the Age of AI
8 minutes read.
Charles-Axel Dein with an interesting take, interestingly enough, similar to how interviews are being done in the labs (e.g. Anthropic and OpenAI). I think that we'll need a test for fundamentals (reasoning, architecture, insights, taste) and a test for using leverage (how to apply AI intelligently)
Read it later via Instapaper.
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8 minutes read.
Charles-Axel Dein with an interesting take, interestingly enough, similar to how interviews are being done in the labs (e.g. Anthropic and OpenAI). I think that we'll need a test for fundamentals (reasoning, architecture, insights, taste) and a test for using leverage (how to apply AI intelligently)
Read it later via Instapaper.
Share it via Twitter or email.
"Cognitive Surrender Is When You Stop Thinking Altogether and Blindly Accept the Answer the AI Gives You" (Video)
2 minutes read.
One minute of a helpful framing (Cognitive Debt and Cognitive Surrender) on seeking the truth instead of following comfort. Very useful as you think of your knowledege and career.
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2 minutes read.
One minute of a helpful framing (Cognitive Debt and Cognitive Surrender) on seeking the truth instead of following comfort. Very useful as you think of your knowledege and career.
Read it later via Instapaper.
Share it via Twitter or email.
Get to the Core of the Thing
3 minutes read.
Brilliant take by Shreyas Doshi, as always: "if you can’t articulate the specific features that would matter, then no framework, sports metaphor, latest podcast anecdote, or Anthropic case study will save you. [...] So whenever someone hands you a binary at altitude dressed up in clever business-speak, whether it’s wide vs. deep, or CAC vs. LTV, or any of the others, your job is to refuse it. Get to the core of the thing. Then talk about that. Everything else is theater."
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3 minutes read.
Brilliant take by Shreyas Doshi, as always: "if you can’t articulate the specific features that would matter, then no framework, sports metaphor, latest podcast anecdote, or Anthropic case study will save you. [...] So whenever someone hands you a binary at altitude dressed up in clever business-speak, whether it’s wide vs. deep, or CAC vs. LTV, or any of the others, your job is to refuse it. Get to the core of the thing. Then talk about that. Everything else is theater."
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Inspiring Tweets
@forgebitz: software engineering in 2026: (1) your package manager is compromised. (2) your cloud provider blocks your account. (3) GitHub itself is hacked. Software is solved
@garrytan: The companies I love working with in office hours are the ones where the founder has a specific, weird, earned insight that nobody else has. Not "AI for X." A genuine edge that came from living inside a problem. The ones that are dying almost always have the same pattern: technically competent founders building something nobody asked for, moving metrics that don't matter, avoiding the conversation with the one user who'd tell them the truth. The lucky thing is that 2nd type of founder can become the 1st kind if they don't stand still, they are willing to talk to people, try things, and always seek high rate of learning.
- Oren
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.