Software Lead Weekly
Issue #704, 22nd May 2026
This Week's Favorite
How to Build a Self-Improving Company With AI (Video)
13 minutes read.
People still like to work in tribes; they still have aspirations for their careers; the pendulum swings, and a new equilibrium will be found with new roles, new ratios (ICs to Managers), and new expectations. Companies that have always had a strong writing culture will be able to find leverage more quickly. So while you're building new feedback loops, remember to seek the truth rather than burning tokens as a core metric.
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13 minutes read.
People still like to work in tribes; they still have aspirations for their careers; the pendulum swings, and a new equilibrium will be found with new roles, new ratios (ICs to Managers), and new expectations. Companies that have always had a strong writing culture will be able to find leverage more quickly. So while you're building new feedback loops, remember to seek the truth rather than burning tokens as a core metric.
Read it later via Instapaper.
Share it via Twitter or email.
Culture
Karpathy Pulling Up to the Office for His First Day on the Research Team @ Anthropic
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.
Everyone Wants to Be AI-pilled. Most Companies Are Still Level 1
8 minutes read.
Having a way to measure "levels" and know where your company stands helps you orient yourself: "Steve Blank once said that a startup is not a small version of a large company. Similarly an AI-pilled company is not simply an AI-assisted version of an old company. They are organizations rebuilt around a new operating model."
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8 minutes read.
Having a way to measure "levels" and know where your company stands helps you orient yourself: "Steve Blank once said that a startup is not a small version of a large company. Similarly an AI-pilled company is not simply an AI-assisted version of an old company. They are organizations rebuilt around a new operating model."
Read it later via Instapaper.
Share it via Twitter or email.
Engineering Metrics for Beginners
7 minutes read.
These metrics, covered by Joseph Gefroh, should serve as a healthy baseline you can align on as a team to serve the business. I agree with Joseph that often looking at trends can provide a better story than a specific measurement: "Ultimately, the important part is to know it’s happening and watch it for changes. If your success rate suddenly drops - that’s an incident you should look into. You system might be running fine, but there’s an outcome issue that needs to be resolved."
Read it later via Instapaper.
Share it via Twitter or email.
7 minutes read.
These metrics, covered by Joseph Gefroh, should serve as a healthy baseline you can align on as a team to serve the business. I agree with Joseph that often looking at trends can provide a better story than a specific measurement: "Ultimately, the important part is to know it’s happening and watch it for changes. If your success rate suddenly drops - that’s an incident you should look into. You system might be running fine, but there’s an outcome issue that needs to be resolved."
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
Observations on Writing With AI
3 minutes read.
"But the imperfections of writing are what make it good writing." -- Above all, good writing feels risky. Putting something out there that doesn't feel like the most probable next token.
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3 minutes read.
"But the imperfections of writing are what make it good writing." -- Above all, good writing feels risky. Putting something out there that doesn't feel like the most probable next token.
Read it later via Instapaper.
Share it via Twitter or email.
The Job Market Is Fine. You Are Not.
8 minutes read.
"learning is free. willingness is the bottleneck." -- Auren Hoffman with a post that feels right for top talent 5 years ago and now becomes the baseline. A world where you have no excuse to wait. A world where the fundamentals will help you explain subtleties in your intuition and the type of experiments you tried.
Read it later via Instapaper.
Share it via Twitter or email.
8 minutes read.
"learning is free. willingness is the bottleneck." -- Auren Hoffman with a post that feels right for top talent 5 years ago and now becomes the baseline. A world where you have no excuse to wait. A world where the fundamentals will help you explain subtleties in your intuition and the type of experiments you tried.
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@readswithravi: In Japanese, “tsundoku” means collecting books and letting them pile up - not for neglect, but for the joy of knowing they're there, full of untold stories.
- 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.