Software Lead Weekly
Issue #695, 20th March 2026
This Week's Favorite
I Told Claude Code to Build Me an Executive Assistant. This Is What My Work as CTO Looks Like Now
9 minutes read.
The ability to offload mental capacity is critical for every leader. On top of that, the ability to track managerial decisions (like engineers use Architecture Decision Records) can help maintain context and improve as a leader. This is the most valuable trait in the system: "This system works because I never think about the system. I think about my work, and the system captures it as a side effect of natural conversation. It's not a todo list I have to maintain. It's not a wiki I have to keep up to date. It's just Claude, always there, always listening, always organizing, always ready to surface exactly what I need."
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9 minutes read.
The ability to offload mental capacity is critical for every leader. On top of that, the ability to track managerial decisions (like engineers use Architecture Decision Records) can help maintain context and improve as a leader. This is the most valuable trait in the system: "This system works because I never think about the system. I think about my work, and the system captures it as a side effect of natural conversation. It's not a todo list I have to maintain. It's not a wiki I have to keep up to date. It's just Claude, always there, always listening, always organizing, always ready to surface exactly what I need."
Read it later via Instapaper.
Share it via Twitter or email.
Culture
They Pulled Off the Impossible: Made a Real Human Video Look 100% AI Generated
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.
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The Marginal Hire
4 minutes read.
AI will drive companies to reduce knowledge-based jobs that are either trivial to learn (e.g., 2-3 weeks of training) or yield the same expected outcome over time. People who will find ways to redefine their work to deliver higher impact will always have a place in the ecosystem. This is why people have been talking nonstop about High Agency over the past 12 months. "Working hands" hiring strategy is no longer acceptable.
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4 minutes read.
AI will drive companies to reduce knowledge-based jobs that are either trivial to learn (e.g., 2-3 weeks of training) or yield the same expected outcome over time. People who will find ways to redefine their work to deliver higher impact will always have a place in the ecosystem. This is why people have been talking nonstop about High Agency over the past 12 months. "Working hands" hiring strategy is no longer acceptable.
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Production Is Where the Rigor Goes
7 minutes read.
"Dashboards are not rigor. Metrics and logs are not rigor. Rigor requires precision: a function of how rich your data is in context and cardinality, and your ability to pick out meaningful events with a scalpel. [...] Any team that wants to reap the benefits of AI is going to have to build the feedback loops we’ve long sought between development (human or agent) and production. They are going to need rich data and precision tools, the ability to trace intent through production and validate it there. The spec describes intent. Telemetry describes reality." -- I love and appreciate how Charity Majors always sets the focus on production as a way to understand the real world.
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7 minutes read.
"Dashboards are not rigor. Metrics and logs are not rigor. Rigor requires precision: a function of how rich your data is in context and cardinality, and your ability to pick out meaningful events with a scalpel. [...] Any team that wants to reap the benefits of AI is going to have to build the feedback loops we’ve long sought between development (human or agent) and production. They are going to need rich data and precision tools, the ability to trace intent through production and validate it there. The spec describes intent. Telemetry describes reality." -- I love and appreciate how Charity Majors always sets the focus on production as a way to understand the real world.
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Interview Coach Skill
7 minutes read.
Simple and pragmatic approach (with Skills) to practice the way you interview. I see individuals use it to improve their chances, and I see companies create shared Skills to train their employees to find the right talent. Being able to simulate the process or to get feedback on it is a great way to improve at it. My only concern with this approach is that I don't see a high signal in it. Showing that you're the best fit for the job is becoming more challenging when everyone feels AI can do a lot of it for you.
Read it later via Instapaper.
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7 minutes read.
Simple and pragmatic approach (with Skills) to practice the way you interview. I see individuals use it to improve their chances, and I see companies create shared Skills to train their employees to find the right talent. Being able to simulate the process or to get feedback on it is a great way to improve at it. My only concern with this approach is that I don't see a high signal in it. Showing that you're the best fit for the job is becoming more challenging when everyone feels AI can do a lot of it for you.
Read it later via Instapaper.
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Peopleware
When Should a Manager Step In?
6 minutes read.
I strongly agree with Charles-Axel Dein's tips for spotting situations where you need to step in as a leader. I'd be careful to frame micro-management as a bad practice, as much as I am with managers being way too distant from reality, and say, "we have to let them learn." Using Andy Grove's Task-Relevant Maturity framework, with an understanding of the implications of a mistake, is a good starting point for judging situations.
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6 minutes read.
I strongly agree with Charles-Axel Dein's tips for spotting situations where you need to step in as a leader. I'd be careful to frame micro-management as a bad practice, as much as I am with managers being way too distant from reality, and say, "we have to let them learn." Using Andy Grove's Task-Relevant Maturity framework, with an understanding of the implications of a mistake, is a good starting point for judging situations.
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How to Sell and Create Awareness
4 minutes read.
Learning to sell your ideas and products is a craft worth learning at every position. It will help you increase your impact, better understand how to pitch your ideas, and think of distribution and utilization as first-class citizens in your product rather than afterthoughts. You can pick up one or two things to do from this great post by Alex Rampell.
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4 minutes read.
Learning to sell your ideas and products is a craft worth learning at every position. It will help you increase your impact, better understand how to pitch your ideas, and think of distribution and utilization as first-class citizens in your product rather than afterthoughts. You can pick up one or two things to do from this great post by Alex Rampell.
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@readswithravi: Marcus Aurelius wrote this over 1800 years ago: “When you arise in the morning think of what a privilege it is to be alive, to think, to enjoy, to love.”
@elvissun: this is the future of saas: one backend with two front doors. one for humans. one for their agents. same building.
- 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.