Software Lead Weekly
Issue #685, 9th January 2026
This Week's Favorite
Outcomes > Learning Opportunities
14 minutes read.
Shreyas Doshi shares an important message: The leader's sole job is to make the company win. Winning companies create a flywheel in which learning opportunities continually emerge. One of my favorite questions to ask leaders is: "How do you learn faster than what the company forces you to do?" to see how they create and formalize a longer-term vision (2-3-year horizon). Shreyas then moves to talk about this post with Claude Chat to stress-test his ideas. This type of work, where you first write and then stress-test it, will become increasingly common. The back and forth between them is fantastic and at times amusing: "I was optimizing for impressive-sounding answers rather than simple true ones. “Company trajectory on your LinkedIn” sounds too obvious to be the real answer. [...] yeah. so after this discussion, tell me which of your original counterarguments still stand. be rigorous and don’t try to please me."
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14 minutes read.
Shreyas Doshi shares an important message: The leader's sole job is to make the company win. Winning companies create a flywheel in which learning opportunities continually emerge. One of my favorite questions to ask leaders is: "How do you learn faster than what the company forces you to do?" to see how they create and formalize a longer-term vision (2-3-year horizon). Shreyas then moves to talk about this post with Claude Chat to stress-test his ideas. This type of work, where you first write and then stress-test it, will become increasingly common. The back and forth between them is fantastic and at times amusing: "I was optimizing for impressive-sounding answers rather than simple true ones. “Company trajectory on your LinkedIn” sounds too obvious to be the real answer. [...] yeah. so after this discussion, tell me which of your original counterarguments still stand. be rigorous and don’t try to please me."
Read it later via Instapaper.
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Culture
ChatGPT Health
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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One of the Earliest Customer Calls I Took Completely Changed the Way I Think About Product Development
4 minutes read.
Reading Grant Lee's post made me think a lot about the products I built in the past and the products we're building now. Most of the products I built made users feel "in control." I can see that we could enhance that to "feel smarter about my business" if we change some aspects of the product and its messaging. Grant writes it well: "Products don't just do things for people. They make people feel a certain way about themselves."
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4 minutes read.
Reading Grant Lee's post made me think a lot about the products I built in the past and the products we're building now. Most of the products I built made users feel "in control." I can see that we could enhance that to "feel smarter about my business" if we change some aspects of the product and its messaging. Grant writes it well: "Products don't just do things for people. They make people feel a certain way about themselves."
Read it later via Instapaper.
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Moving Away From Agile: What's Next (Video)
22 minutes read.
I'm not a big fan of the word Agile and most of the empty-calorie practices behind it, done without proper reasoning, as they've completely lost their meaning. The work done by Martin Harrysson and Natasha Maniar to better explore how companies leverage GenAI tools considers their processes going forward. Stay critical and critique everything. Make sure you put in place a process only where inertia fails you. Mindlessly following trends and "best practices" will slow you down.
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22 minutes read.
I'm not a big fan of the word Agile and most of the empty-calorie practices behind it, done without proper reasoning, as they've completely lost their meaning. The work done by Martin Harrysson and Natasha Maniar to better explore how companies leverage GenAI tools considers their processes going forward. Stay critical and critique everything. Make sure you put in place a process only where inertia fails you. Mindlessly following trends and "best practices" will slow you down.
Read it later via Instapaper.
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High Agency Is Often Mistaken for Speed
4 minutes read.
Hiten Shah is spot on: "High-agency people do something different. They shorten the time between an idea and its first collision with the real world. They build the smallest version that can reveal a truth. They ask the customer before polishing the story. They test behavior before optimizing the process. They trade speculation for evidence, not because they enjoy being wrong, but because every collision with reality sharpens their understanding of what actually works."
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4 minutes read.
Hiten Shah is spot on: "High-agency people do something different. They shorten the time between an idea and its first collision with the real world. They build the smallest version that can reveal a truth. They ask the customer before polishing the story. They test behavior before optimizing the process. They trade speculation for evidence, not because they enjoy being wrong, but because every collision with reality sharpens their understanding of what actually works."
Read it later via Instapaper.
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Peopleware
Creating Space: Do Less, to Create the Space to Be Great.
4 minutes read.
"When you stop trying to “find the balance” in everything, you create space to maximize the one choice that creates clarity and strength. When you stop trying to “have it all,” you create the space to deeply experience the few things that are most important." -- Jason Cohen reminds us about the need to clear things out to let important things take place.
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4 minutes read.
"When you stop trying to “find the balance” in everything, you create space to maximize the one choice that creates clarity and strength. When you stop trying to “have it all,” you create the space to deeply experience the few things that are most important." -- Jason Cohen reminds us about the need to clear things out to let important things take place.
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Coding Agents & Complexity Budgets
5 minutes read.
More and more teams will start asking this question of "should we really buy this software or just build it ourselves?" like Lee Robinson and his team did: "With AI and coding agents, the cost of an abstraction has never been higher. I asked them: do we really need a CMS? Will people care if they have to use a chatbot to modify content versus a GUI? We could eliminate so much complexity if we just went back to the raw code."
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5 minutes read.
More and more teams will start asking this question of "should we really buy this software or just build it ourselves?" like Lee Robinson and his team did: "With AI and coding agents, the cost of an abstraction has never been higher. I asked them: do we really need a CMS? Will people care if they have to use a chatbot to modify content versus a GUI? We could eliminate so much complexity if we just went back to the raw code."
Read it later via Instapaper.
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My Second Brain Agentic System
4 minutes read.
We'll see many people building personal systems to help them feel more in control and more positive in how they live their lives. Having a builder available for us to think of as a PM and a coder can generate a wonderful, highly personalized experience. This example by Ashe of building an Ashe AI might inspire you to build your own "second brain".
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4 minutes read.
We'll see many people building personal systems to help them feel more in control and more positive in how they live their lives. Having a builder available for us to think of as a PM and a coder can generate a wonderful, highly personalized experience. This example by Ashe of building an Ashe AI might inspire you to build your own "second brain".
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@aarondfrancis: 2021: it can’t even autocomplete a line 2022: it can’t even write a whole function 2023: it can’t even pass a coding interview 2024: it can’t even build an app 2025: it can’t even handle complex projects 2026: oh no
- 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.