Software Lead Weekly
Issue #691, 20th February 2026
This Week's Favorite
Minions: Stripe’s One-Shot, End-to-End Coding Agents
7 minutes read.
Companies will need to operate execution units (minions, agents, whatever) while figuring out how to do that safely and effectively. It's getting x10 harder when dealing with systems at a massive scale and with tight requirements around security and availability: "LLM agents are incredibly good at building software from scratch when there are relatively few constraints on a system. However, iterating on any codebase of the scale, complexity, and maturity of Stripe’s is inherently much harder. Humans must build sophisticated mental models to make effective changes in our repos, and enabling agents to develop the correct intuitions and use the correct tools within the confines of their context windows is challenging."
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7 minutes read.
Companies will need to operate execution units (minions, agents, whatever) while figuring out how to do that safely and effectively. It's getting x10 harder when dealing with systems at a massive scale and with tight requirements around security and availability: "LLM agents are incredibly good at building software from scratch when there are relatively few constraints on a system. However, iterating on any codebase of the scale, complexity, and maturity of Stripe’s is inherently much harder. Humans must build sophisticated mental models to make effective changes in our repos, and enabling agents to develop the correct intuitions and use the correct tools within the confines of their context windows is challenging."
Read it later via Instapaper.
Share it via Twitter or email.
Culture
As Predicted, the Ninjas Will Lose Their Jobs First to AI
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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Share it via Twitter or email.
Should Managers Become Hands-on Again?
5 minutes read.
Yes. They should. The tools make this question almost irrelevant given how different the experience is to write software. Building products and systems is how you develop intuition (“what can we sell?”, “how do we penetrate the market?”), inspire others, and identify high-leverage areas worth investing in. Building products and systems is how you learn to pitch and experiment with the WHY and WHAT you should do, as the HOW is getting easier with agentic development. It's about gaining better clarity on org design and the missing fundamentals (talent, infrastructure, processes) that require your attention.
Read it later via Instapaper.
Share it via Twitter or email.
5 minutes read.
Yes. They should. The tools make this question almost irrelevant given how different the experience is to write software. Building products and systems is how you develop intuition (“what can we sell?”, “how do we penetrate the market?”), inspire others, and identify high-leverage areas worth investing in. Building products and systems is how you learn to pitch and experiment with the WHY and WHAT you should do, as the HOW is getting easier with agentic development. It's about gaining better clarity on org design and the missing fundamentals (talent, infrastructure, processes) that require your attention.
Read it later via Instapaper.
Share it via Twitter or email.
Your Org Structure Is My Opportunity
4 minutes read.
Share this post with your teammates and observe your company. Are you starting to think about your talent, org design, and infrastructure differently? "The distance between idea and done is basically zero now, for everyone, and most companies are still organized around a distance that no longer exists. [...] Your company still has a role for every function and a gap between each one. Those gaps add up to weeks, and in those weeks your customers are already talking to someone who doesn't work that way."
Read it later via Instapaper.
Share it via Twitter or email.
4 minutes read.
Share this post with your teammates and observe your company. Are you starting to think about your talent, org design, and infrastructure differently? "The distance between idea and done is basically zero now, for everyone, and most companies are still organized around a distance that no longer exists. [...] Your company still has a role for every function and a gap between each one. Those gaps add up to weeks, and in those weeks your customers are already talking to someone who doesn't work that way."
Read it later via Instapaper.
Share it via Twitter or email.
Harness Engineering
5 minutes read.
Birgitta Böckeler is spot on with this: "As coding becomes less about typing code and more about steering its generation, AI might push us toward fewer tech stacks. Usability of frameworks and SDKs still matters — we’re seeing repeatedly that what’s good for humans is good for AI. But developer tastes will matter less at that level of detail. Little inefficiencies and idiosyncracies in interfaces will be less annoying since we don’t deal with them directly. We might choose stacks with good harnesses available and prioritize “AI-friendliness”."
Read it later via Instapaper.
Share it via Twitter or email.
5 minutes read.
Birgitta Böckeler is spot on with this: "As coding becomes less about typing code and more about steering its generation, AI might push us toward fewer tech stacks. Usability of frameworks and SDKs still matters — we’re seeing repeatedly that what’s good for humans is good for AI. But developer tastes will matter less at that level of detail. Little inefficiencies and idiosyncracies in interfaces will be less annoying since we don’t deal with them directly. We might choose stacks with good harnesses available and prioritize “AI-friendliness”."
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
10 Fundamental (But Really Hard) Security Metrics
8 minutes read.
Phil Venables shares a set of good security metrics for you to use, with a clear motivation to do so beyond security posture: "However, as I think about this more I am becoming more certain that we have to do this. Perhaps not exactly the ideas and examples I give below, but something similar and maybe better. The main point, though, is that these metrics aren’t necessarily to be driven to 100% (or 0 depending on the measure). Rather, organizations can choose where to set their goal and hence risk appetite. Achieving the set goals defined by the metrics should all also create adjacent benefits more than just mitigating cybersecurity risk - this could be to drive the modernization of the technology environment with all those commercial or mission benefits that come from that. Even the act of figuring how to measure these will bring improvements in and of itself."
Read it later via Instapaper.
Share it via Twitter or email.
8 minutes read.
Phil Venables shares a set of good security metrics for you to use, with a clear motivation to do so beyond security posture: "However, as I think about this more I am becoming more certain that we have to do this. Perhaps not exactly the ideas and examples I give below, but something similar and maybe better. The main point, though, is that these metrics aren’t necessarily to be driven to 100% (or 0 depending on the measure). Rather, organizations can choose where to set their goal and hence risk appetite. Achieving the set goals defined by the metrics should all also create adjacent benefits more than just mitigating cybersecurity risk - this could be to drive the modernization of the technology environment with all those commercial or mission benefits that come from that. Even the act of figuring how to measure these will bring improvements in and of itself."
Read it later via Instapaper.
Share it via Twitter or email.
How to Solve Any Problem
5 minutes read.
"Queen Elizabeth didn’t error correct. She had an error, her teeth were getting blacker, but she kept rubbing sugar on her decaying mouth. [...] Now, are you going to make new guesses about your problems or assume nothing can be done? Are you going to test your guesses or assume they're correct? And are you going to error correct or deny reality?" -- Wonderful take on how we innovate faster than we can grasp (e.g., the past 100 years versus the 1000 years before that), and how the Scientific method changed everything for humanity.
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5 minutes read.
"Queen Elizabeth didn’t error correct. She had an error, her teeth were getting blacker, but she kept rubbing sugar on her decaying mouth. [...] Now, are you going to make new guesses about your problems or assume nothing can be done? Are you going to test your guesses or assume they're correct? And are you going to error correct or deny reality?" -- Wonderful take on how we innovate faster than we can grasp (e.g., the past 100 years versus the 1000 years before that), and how the Scientific method changed everything for humanity.
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Inspiring Tweets
@tobi: Running a company is just context engineering internally. Now that skill has even more value in the agentic world. Us tech founders have been doing reps to prepare for this.
- 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.