Software Lead Weekly
Issue #678, 21st November 2025
This Week's Favorite
Curate People (Podcast)
52 minutes read.
Hiring is the most important task for leaders who need to build a team to achieve a mission. I loved Naval's view on "Every Great Engineer Is Also an Artist" and "Break Every Rule to Get the Best People". This can be true for rules that candidates care about, but, even more importantly, for rules that the company demands leaders follow. You cannot hire the best if you follow boring, tedious guidelines. It doesn't mean you need to be reckless. Creativity comes from understanding reasonable constraints (e.g., legal or sometimes moral) and operating within them in a way that others will feel is "it's not scalable". Do that.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
52 minutes read.
Hiring is the most important task for leaders who need to build a team to achieve a mission. I loved Naval's view on "Every Great Engineer Is Also an Artist" and "Break Every Rule to Get the Best People". This can be true for rules that candidates care about, but, even more importantly, for rules that the company demands leaders follow. You cannot hire the best if you follow boring, tedious guidelines. It doesn't mean you need to be reckless. Creativity comes from understanding reasonable constraints (e.g., legal or sometimes moral) and operating within them in a way that others will feel is "it's not scalable". Do that.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Culture
Peak Software Engineers Fashion.
1 minutes read.
My humble effort to help you start the weekend with a smile.
Read it later via Pocket or 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 Pocket or Instapaper.
Share it via Twitter or email.
Flexible Code, Rigid Org
5 minutes read.
Aviv Ben-Yosef writes so well: "We design org charts like medieval fiefdoms, then wonder why our architecture looks like a border map." and "PMs feel pressured to feed the beast—as if engineers will starve without Jira tickets. Roadmaps get driven by the need to look busy, not by actual impact." and finally "Reward those who simplify, not those who expose their brilliance with complex and clever solutions."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
5 minutes read.
Aviv Ben-Yosef writes so well: "We design org charts like medieval fiefdoms, then wonder why our architecture looks like a border map." and "PMs feel pressured to feed the beast—as if engineers will starve without Jira tickets. Roadmaps get driven by the need to look busy, not by actual impact." and finally "Reward those who simplify, not those who expose their brilliance with complex and clever solutions."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
AI Eats the World (Video)
22 minutes read.
Benedict Evans's biannual overview is always worth the time. "Do we use LLMs to control all of our traditional software? Or are LLMs just another API to build software?" is the main question many of us deal with when building products.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
22 minutes read.
Benedict Evans's biannual overview is always worth the time. "Do we use LLMs to control all of our traditional software? Or are LLMs just another API to build software?" is the main question many of us deal with when building products.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Most of the Fastest-Growing AI App Companies Today Are PLG
3 minutes read.
"Delight drives adoption. Moats drive endurance. The strongest PLG businesses turned usage into compounding advantage—through network effects (Slack, Figma, Canva), data loops and integrations (Notion, Airtable), or workflow lock-in (Zoom). Most AI PLG companies today are still in “demo-wow” mode, not “moat-building” mode. Without elements like network effects, switching is easy. One emerging AI moat might be memory. I find myself returning to ChatGPT because it knows my preferences and tailors its responses accordingly. Have you seen other compelling examples of this at the AI app layer?" -- I used Jake Saper's take at least 5 times this week in different conversations when thinking about next year's planning.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
3 minutes read.
"Delight drives adoption. Moats drive endurance. The strongest PLG businesses turned usage into compounding advantage—through network effects (Slack, Figma, Canva), data loops and integrations (Notion, Airtable), or workflow lock-in (Zoom). Most AI PLG companies today are still in “demo-wow” mode, not “moat-building” mode. Without elements like network effects, switching is easy. One emerging AI moat might be memory. I find myself returning to ChatGPT because it knows my preferences and tailors its responses accordingly. Have you seen other compelling examples of this at the AI app layer?" -- I used Jake Saper's take at least 5 times this week in different conversations when thinking about next year's planning.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Peopleware
Continual Learning Explains Some Interesting Phenomena in Human Memory
8 minutes read.
Beren Millidge with a brilliant post that made me think about how to build memory around LLMs and switch between different models while retaining the same interpretation of the world.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
8 minutes read.
Beren Millidge with a brilliant post that made me think about how to build memory around LLMs and switch between different models while retaining the same interpretation of the world.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Fear of Sales
6 minutes read.
An old post by Elad Gil that remains relevant today, as it always has. Companies can leverage an effective sales team when the economics make sense to put the right incentives in place to benefit the company and the sellers. In today's AI era, these sellers can become even more effective and efficient if they have the right mindset and the company provides the right tools to define focus areas (who to sell to) and create "pull" (customers will beg for your product).
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
6 minutes read.
An old post by Elad Gil that remains relevant today, as it always has. Companies can leverage an effective sales team when the economics make sense to put the right incentives in place to benefit the company and the sellers. In today's AI era, these sellers can become even more effective and efficient if they have the right mindset and the company provides the right tools to define focus areas (who to sell to) and create "pull" (customers will beg for your product).
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Leading Through Inspiration
5 minutes read.
"leadership = intelligence \* virtue \* inspiration" -- Andrew Davis drew a powerful (and easy enough to remember) formula and provides some great takes on inspiring others by being inspired first: "Just as the basic foundation for winning others trust is to becoming trustworthy. So too, if you want to inspire others, the basic foundation is becoming inspired. [...] Inspiration is all around us. There is never a moment when there’s not something that we can draw inspiration from. Look at how fascinated a child can be with a stone or a feather. This is because their mind is wide open. They are rapidly taking in new information. They’re studying the world. [...] it’s critical that all of us seek inspiration and try to offer inspiration to others. Especially if we hope to lead others in a beneficial direction, it’s not enough to just become trustworthy. We need to offer others inspiration."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
5 minutes read.
"leadership = intelligence \* virtue \* inspiration" -- Andrew Davis drew a powerful (and easy enough to remember) formula and provides some great takes on inspiring others by being inspired first: "Just as the basic foundation for winning others trust is to becoming trustworthy. So too, if you want to inspire others, the basic foundation is becoming inspired. [...] Inspiration is all around us. There is never a moment when there’s not something that we can draw inspiration from. Look at how fascinated a child can be with a stone or a feather. This is because their mind is wide open. They are rapidly taking in new information. They’re studying the world. [...] it’s critical that all of us seek inspiration and try to offer inspiration to others. Especially if we hope to lead others in a beneficial direction, it’s not enough to just become trustworthy. We need to offer others inspiration."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@garrytan: Human in the loop and UX are still key. You must design workflows where a human stays in the loop just enough to handle risk, but not so much that you lose the efficiency.
@brian_armstrong: One of my favorite lessons I’ve learnt from working with smart people: Action produces information. If you’re unsure of what to do, just do anything, even if it’s the wrong thing. This will give you information about what you should actually be doing. Sounds simple on the surface - the hard part is making it part of your every day working process.
- 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.