Software Lead Weekly
Issue #712, 17th July 2026
This Week's Favorite
The Archaeologist’s Copilot: Restoration of a 20-Year-Old Java “Big Ball of Mud” Using AI and Docker
18 minutes read.
The biggest lesson I took from this refactoring project is to rely on a fundamental understanding of software development (and maintenance) to set the right goals first: a system verification mechanism that you can trust.
Read it later via Instapaper.
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18 minutes read.
The biggest lesson I took from this refactoring project is to rely on a fundamental understanding of software development (and maintenance) to set the right goals first: a system verification mechanism that you can trust.
Read it later via Instapaper.
Share it via Twitter or email.
Culture
Happy End of Q2
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 Four Core Areas of Responsibility for an Engineering Manager
8 minutes read.
James Samuel makes a point worth repeating: management exists to amplify the collective impact of a team, not to add a layer between people and the work (so the impact of 5 ICs + 1 EM > 6 ICs). Once an org outgrows a flat structure, someone still has to hold coordination, prioritization, and alignment together, or the team's output stops compounding. Are you spending your week amplifying your team, or just adding overhead on top of it?
Read it later via Instapaper.
Share it via Twitter or email.
8 minutes read.
James Samuel makes a point worth repeating: management exists to amplify the collective impact of a team, not to add a layer between people and the work (so the impact of 5 ICs + 1 EM > 6 ICs). Once an org outgrows a flat structure, someone still has to hold coordination, prioritization, and alignment together, or the team's output stops compounding. Are you spending your week amplifying your team, or just adding overhead on top of it?
Read it later via Instapaper.
Share it via Twitter or email.
The Reverse Information Paradox
3 minutes read.
Satya Nadella flips Kenneth Arrow's old information paradox on its head: buyers used to risk getting information for free once they'd seen it, but with AI the buyer now risks giving their own proprietary knowledge away just to make the model useful to them. Every prompt, correction, and workflow fed into a model is institutional know-how leaking out one trace at a time, and unlike Arrow's original problem, there's no patent system yet built to protect it. What would it take for your company to actually own the learning loop it's paying to create?
Read it later via Instapaper.
Share it via Twitter or email.
3 minutes read.
Satya Nadella flips Kenneth Arrow's old information paradox on its head: buyers used to risk getting information for free once they'd seen it, but with AI the buyer now risks giving their own proprietary knowledge away just to make the model useful to them. Every prompt, correction, and workflow fed into a model is institutional know-how leaking out one trace at a time, and unlike Arrow's original problem, there's no patent system yet built to protect it. What would it take for your company to actually own the learning loop it's paying to create?
Read it later via Instapaper.
Share it via Twitter or email.
Slow Down to Speed Up: AI and Software Engineering (Video)
52 minutes read.
How much of your codebase would your team actually vouch for if you asked them today? I think this is the question you should lead with, and make sure you leverage AI to first get it to a good-enough number. It's easiest to measure by maintenance cost (e.g., can you solve tickets automatically? Can you handle the toil of keeping the system running automatically?), and then see how much faster the initial estimate for adding new capabilities is compared to the actual delivery time (with high quality). Gergely Orosz shares great observations and important insights on where to invest in your career in the era of AI.
Read it later via Instapaper.
Share it via Twitter or email.
52 minutes read.
How much of your codebase would your team actually vouch for if you asked them today? I think this is the question you should lead with, and make sure you leverage AI to first get it to a good-enough number. It's easiest to measure by maintenance cost (e.g., can you solve tickets automatically? Can you handle the toil of keeping the system running automatically?), and then see how much faster the initial estimate for adding new capabilities is compared to the actual delivery time (with high quality). Gergely Orosz shares great observations and important insights on where to invest in your career in the era of AI.
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
Good Tools Are Invisible
5 minutes read.
The fact is that people tie tools to their identity when it comes to their craftsmanship (how you hold a knife as a Chef, or which editor you use as a software engineer). You can develop skills in how you use them, then demonstrate it to others to claim superiority (real or not). This is part of human nature. My takeaway from this post is that we should be careful not to use it when designing products we build for others, as often their identity is not tied to the tool you build for them: "But a learning curve is a cost, not a virtue. It could hypothetically be absolutely a cost worth paying, but the payoff has to be genuine productivity, not the satisfaction of having paid it. Too often the reasoning is just sunk-cost dressed up as merit."
Read it later via Instapaper.
Share it via Twitter or email.
5 minutes read.
The fact is that people tie tools to their identity when it comes to their craftsmanship (how you hold a knife as a Chef, or which editor you use as a software engineer). You can develop skills in how you use them, then demonstrate it to others to claim superiority (real or not). This is part of human nature. My takeaway from this post is that we should be careful not to use it when designing products we build for others, as often their identity is not tied to the tool you build for them: "But a learning curve is a cost, not a virtue. It could hypothetically be absolutely a cost worth paying, but the payoff has to be genuine productivity, not the satisfaction of having paid it. Too often the reasoning is just sunk-cost dressed up as merit."
Read it later via Instapaper.
Share it via Twitter or email.
How to Be Good at Research
6 minutes read.
I love this statement so much: "retire the idea that engineering is the junior partner here. at the frontier the two jobs have fused. the researcher who can build the harness, the eval, and the data pipeline is the one whose hypotheses actually get tested. everyone else is waiting in a queue."
Read it later via Instapaper.
Share it via Twitter or email.
6 minutes read.
I love this statement so much: "retire the idea that engineering is the junior partner here. at the frontier the two jobs have fused. the researcher who can build the harness, the eval, and the data pipeline is the one whose hypotheses actually get tested. everyone else is waiting in a queue."
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@readswithravi: Kobe Bryant once said: “Everyone wants to be a beast. Everyone wants to be the best. But very few people are willing to do what it actually takes. Because what it takes is boring. It is waking up at 4:00 AM. It is shooting the same shot a thousand times. It is watching the film when you are tired. People fall in love with the result, but they hate the process. You have to fall in love with the boredom. You have to fall in love with the repetition. If you can find joy in the mundane work that no one else sees, the lights will eventually shine on you.”
@AlexHormozi: Friendly reminder that no one gives a shit about the reason you didn’t make it happen.
- 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.