Software Lead Weekly 
Issue #718, 28th August 2026
This Week's Favorite
Tokens, Hours, Points, and Other Curious Proxies
11 minutes read.
John Cutler's alternative to ROI theater: treat the team as a single cost unit ("this team costs $1.5M a year, salaries and tokens"), tie it to a causal model of business value, and stop pretending hours or tokens can be meaningfully decomposed into attribution. Worth trying to run an exercise with your team to fill in the questions under "What theory of the system are we betting on" and see where you see alignment and where it would be useful to debate the differences.
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11 minutes read.
John Cutler's alternative to ROI theater: treat the team as a single cost unit ("this team costs $1.5M a year, salaries and tokens"), tie it to a causal model of business value, and stop pretending hours or tokens can be meaningfully decomposed into attribution. Worth trying to run an exercise with your team to fill in the questions under "What theory of the system are we betting on" and see where you see alignment and where it would be useful to debate the differences.
Read it later via Instapaper.
Share it via Twitter or email.
Culture
Had a Very San Francisco Morning in My Home
1 minutes read.
My humble effort to help you start the weekend with a smile.
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1 minutes read.
My humble effort to help you start the weekend with a smile.
Read it later via Instapaper.
Share it via Twitter or email.
The Drucker Drift
2 minutes read.
Classic Seth, concise and to the point: "Corporations are a cultural fiction, something we created and permit to exist because it serves the community. In exchange for leverage and insulation, the corporations are expected to be of use and to improve conditions for those they serve–not to be a tool to enrich a few shareholders."
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2 minutes read.
Classic Seth, concise and to the point: "Corporations are a cultural fiction, something we created and permit to exist because it serves the community. In exchange for leverage and insulation, the corporations are expected to be of use and to improve conditions for those they serve–not to be a tool to enrich a few shareholders."
Read it later via Instapaper.
Share it via Twitter or email.
The Value of Getting Closer to the Work
5 minutes read.
This is my biggest takeaway from the post: "Before, the discipline was: you found a bug, you wrote a test so it wouldn’t come back. Good practice. Now, I do that, and then I ask: how do we guard against this class of problem? Competent humans rarely make the same mistake twice. AI will make the same mistake endlessly." The work is still clarity: what's expected, who owns what, what good looks like.
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5 minutes read.
This is my biggest takeaway from the post: "Before, the discipline was: you found a bug, you wrote a test so it wouldn’t come back. Good practice. Now, I do that, and then I ask: how do we guard against this class of problem? Competent humans rarely make the same mistake twice. AI will make the same mistake endlessly." The work is still clarity: what's expected, who owns what, what good looks like.
Read it later via Instapaper.
Share it via Twitter or email.
You Are Not a Model. Don’t Price Per Token.
6 minutes read.
Learning about pricing and packaging is incredibly important as a builder. Mistakes in pricing and packaging can create wrong expectations with buyers (e.g., expecting to get things for free) or keep you from building healthy, sustainable margins (e.g., charging the cost of the model you use plus your margins). Learn from Tugce Erten and Sarah Wang, it can influence your decisions on what to build and how to pick features so you can anchor pricing accordingly.
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6 minutes read.
Learning about pricing and packaging is incredibly important as a builder. Mistakes in pricing and packaging can create wrong expectations with buyers (e.g., expecting to get things for free) or keep you from building healthy, sustainable margins (e.g., charging the cost of the model you use plus your margins). Learn from Tugce Erten and Sarah Wang, it can influence your decisions on what to build and how to pick features so you can anchor pricing accordingly.
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
Harnesses Are Situated Agents
4 minutes read.
This made me click, so I appreciate this framing by Drew Breunig: "Harrison’s 4 elements of an agent remain – the system prompt, planning tool, file system, and subgents – describing the core loop. This is the core loop the developer controls with the keyboard. The harness manages everything beyond this, the world the developer sits within. [...] People at Cursor and Copilot are nodding right now, welcoming us all, wondering what took so long." Did you consider building your harness? What does it include? How clearly have you made the separation of concerns so you can innovate where it matters to your company?
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4 minutes read.
This made me click, so I appreciate this framing by Drew Breunig: "Harrison’s 4 elements of an agent remain – the system prompt, planning tool, file system, and subgents – describing the core loop. This is the core loop the developer controls with the keyboard. The harness manages everything beyond this, the world the developer sits within. [...] People at Cursor and Copilot are nodding right now, welcoming us all, wondering what took so long." Did you consider building your harness? What does it include? How clearly have you made the separation of concerns so you can innovate where it matters to your company?
Read it later via Instapaper.
Share it via Twitter or email.
Roblox CEO: How to Make Better Decisions by Fixing Yourself First (Video)
45 minutes read.
"If one is not reducing bureaucracy, there's no neutral ground. If one is not trying to improve things, it is going backwards." -- David Baszucki, Roblox's co-founder and CEO, rejects the idea of a stable, steady state inside a company: what looks calm is quietly rotting. When did you last assume a process was fine simply because nobody was complaining about it?
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45 minutes read.
"If one is not reducing bureaucracy, there's no neutral ground. If one is not trying to improve things, it is going backwards." -- David Baszucki, Roblox's co-founder and CEO, rejects the idea of a stable, steady state inside a company: what looks calm is quietly rotting. When did you last assume a process was fine simply because nobody was complaining about it?
Read it later via Instapaper.
Share it via Twitter or email.
Career Advice in the Age of AI
6 minutes read.
Phil Chen is spot on that the median output today is just "what an agent can produce with a sloppy prompt": "Value therefore comes from providing a unique perspective on a slice of problems or attention to detail." I'd push that further: the last mile was always the differentiator, AI just made it visible to everyone at once by collapsing the cost of the first 90%.
Read it later via Instapaper.
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6 minutes read.
Phil Chen is spot on that the median output today is just "what an agent can produce with a sloppy prompt": "Value therefore comes from providing a unique perspective on a slice of problems or attention to detail." I'd push that further: the last mile was always the differentiator, AI just made it visible to everyone at once by collapsing the cost of the first 90%.
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@romxdev: The hardest part of software engineering is convincing people that a simple solution is actually better than an impressive one
@Saanvi_dhillon: Unpopular opinion: “AI makes everyone a developer” is true in the same way cameras made everyone a photographer
- 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.