Software Lead Weekly 
Issue #726, 23rd October 2026
This Week's Favorite
How to Scale Intent, Quality, and Artistry With Al (Video)
22 minutes read.
Great talk by Katie Dill (Stripe) on keeping craft alive in the AI building boom: "Previously, a quality filter was essentially built into every stage of the product development process [...] Now we can generate 20 ideas a week. [...] the filtering that used to be throughout the process now has to happen after creation, when it's much harder to say 'no.'" -- I agree, and it makes the editor the most underrated role in an AI-heavy org: someone who looks at the whole product end to end, not each shiny piece. Who plays that role on your team today?
Read it later via Instapaper.
Share it via Twitter or email.
22 minutes read.
Great talk by Katie Dill (Stripe) on keeping craft alive in the AI building boom: "Previously, a quality filter was essentially built into every stage of the product development process [...] Now we can generate 20 ideas a week. [...] the filtering that used to be throughout the process now has to happen after creation, when it's much harder to say 'no.'" -- I agree, and it makes the editor the most underrated role in an AI-heavy org: someone who looks at the whole product end to end, not each shiny piece. Who plays that role on your team today?
Read it later via Instapaper.
Share it via Twitter or email.
Culture
LGTM (Looks Good to Me) - Claude Opus 5.5 Music Video
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.
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.
Good Interfaces Make Good Neighbors
3 minutes read.
Andrew Bosworth's checklist (owner, ordered priorities, process for new work) is getting much easier to follow. With the right context and AI to wrap it nicely, we can draw these interfaces and keep them up to date with minimal manual effort, which was the real reason they used to rot.
Read it later via Instapaper.
Share it via Twitter or email.
3 minutes read.
Andrew Bosworth's checklist (owner, ordered priorities, process for new work) is getting much easier to follow. With the right context and AI to wrap it nicely, we can draw these interfaces and keep them up to date with minimal manual effort, which was the real reason they used to rot.
Read it later via Instapaper.
Share it via Twitter or email.
If Your Team Is Too Busy Doing Their 'Normal Job' to Experiment With AI, You're Preparing Them to Be Replaced
4 minutes read.
Great provocation by Geoffrey Huntley for any engineering leader. His claim is that "too busy" is a leadership choice, not a fact about the team, and that the gap between engineers who use AI and those who don't will show up (probably already showing up) in performance rankings within months. AI fluency is a visible skill to own, not an optional hobby.
Read it later via Instapaper.
Share it via Twitter or email.
4 minutes read.
Great provocation by Geoffrey Huntley for any engineering leader. His claim is that "too busy" is a leadership choice, not a fact about the team, and that the gap between engineers who use AI and those who don't will show up (probably already showing up) in performance rankings within months. AI fluency is a visible skill to own, not an optional hobby.
Read it later via Instapaper.
Share it via Twitter or email.
Assorted Things I've Been Mulling Over Regarding Agents in the Economy
3 minutes read.
Patrick Collison shares a useful framing on what personal agents change for companies: "Personal agents will, I think, act as a kind of structural subsidy for product quality. How would markets look different if individuals always spent at least 10 hours researching their purchases? On the margin, focusing on making a product better is, I think, going to become a more effective strategy for companies." The same applies to how we build products with AI: if the buyer is an agent, distribution tricks and attention hacks matter less, and the quality of the core experience (and the data that proves it) matters more.
Read it later via Instapaper.
Share it via Twitter or email.
3 minutes read.
Patrick Collison shares a useful framing on what personal agents change for companies: "Personal agents will, I think, act as a kind of structural subsidy for product quality. How would markets look different if individuals always spent at least 10 hours researching their purchases? On the margin, focusing on making a product better is, I think, going to become a more effective strategy for companies." The same applies to how we build products with AI: if the buyer is an agent, distribution tricks and attention hacks matter less, and the quality of the core experience (and the data that proves it) matters more.
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
I Am Often Wrong (Boris Cherny, the Creator of Claude Code)
3 minutes read.
This should be part of Boris's README on how he drives decisions (I created [https://managerreadme.com](http://managerreadme.com "") years ago to address it from a management perspective). With AI making it cheap to build almost anything, a fuzzy problem now produces complex plans and unclear success criteria faster than ever.
Read it later via Instapaper.
Share it via Twitter or email.
3 minutes read.
This should be part of Boris's README on how he drives decisions (I created [https://managerreadme.com](http://managerreadme.com "") years ago to address it from a management perspective). With AI making it cheap to build almost anything, a fuzzy problem now produces complex plans and unclear success criteria faster than ever.
Read it later via Instapaper.
Share it via Twitter or email.
You Have More Influence Over the Future Than You Think
6 minutes read.
Great short read to forward to your team before the next roadmap or planning session. Sharif Shameem notes that daily life looks much like 50 years ago, and that people who see AI only as a way to automate knowledge work lack imagination. Read it for the closing line, "the best way to predict the future is to invent it", then ask what you would build if your goal were improving customers' lives, not just making work more efficient.
Read it later via Instapaper.
Share it via Twitter or email.
6 minutes read.
Great short read to forward to your team before the next roadmap or planning session. Sharif Shameem notes that daily life looks much like 50 years ago, and that people who see AI only as a way to automate knowledge work lack imagination. Read it for the closing line, "the best way to predict the future is to invent it", then ask what you would build if your goal were improving customers' lives, not just making work more efficient.
Read it later via Instapaper.
Share it via Twitter or email.
Room for Ambition
3 minutes read.
Karri Saarinen (founder of Linear) describes what a team culture can give people: "You don't need to agree with every idea. But there is a room, or an environment, that gives ambition space. Often, the support is simple: listening seriously, sharing an idea or a story, making an introduction. Helping where you can without assuming you know what someone should do." I like this as a definition of what leaders can offer their teams.
Read it later via Instapaper.
Share it via Twitter or email.
3 minutes read.
Karri Saarinen (founder of Linear) describes what a team culture can give people: "You don't need to agree with every idea. But there is a room, or an environment, that gives ambition space. Often, the support is simple: listening seriously, sharing an idea or a story, making an introduction. Helping where you can without assuming you know what someone should do." I like this as a definition of what leaders can offer their teams.
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@hadari_o: Sure, blame Claude for your change that trashed prod but take credit for the html report "you made"
- 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.