Software Lead Weekly
Issue #680, 5th December 2025
This Week's Favorite
What Is Al "Reward Hacking"—and Why Do We Worry About It? (Video)
52 minutes read.
I love everything in this conversation. Nerds are winning with passion, brainpower, and endless curiosity to deeply understand their domains while remaining playful. “When the model learns to do these hacks, it becomes evil” (e.g., learning how to pass eval checks by finding hacks to pass the tests) is a frightening topic to consider as we move more and more of our stack to be based on LLM models. This is a fascinating discussion you should listen to if you want to understand better how the big players in this field build and optimize (including safety) the models we all use in production.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
52 minutes read.
I love everything in this conversation. Nerds are winning with passion, brainpower, and endless curiosity to deeply understand their domains while remaining playful. “When the model learns to do these hacks, it becomes evil” (e.g., learning how to pass eval checks by finding hacks to pass the tests) is a frightening topic to consider as we move more and more of our stack to be based on LLM models. This is a fascinating discussion you should listen to if you want to understand better how the big players in this field build and optimize (including safety) the models we all use in production.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Culture
How It Feels to Be a Founder
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.
To Launch Something New, You Need "Social Dandelions”
12 minutes read.
Mapping the qualities you should seek when pitching your idea to a community is a great framing to consider when you want to create this initial momentum. This is true when pitching an idea with your company or when starting a new business. It made me think a lot about how I promoted my ideas and how little thought I put into them. I wish I had read this post 15 years ago.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
12 minutes read.
Mapping the qualities you should seek when pitching your idea to a community is a great framing to consider when you want to create this initial momentum. This is true when pitching an idea with your company or when starting a new business. It made me think a lot about how I promoted my ideas and how little thought I put into them. I wish I had read this post 15 years ago.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Vercel's AI Sales Agent : 10 SDRs Down to 1 in Six Weeks (9 Moved to Outbound)
3 minutes read.
This all leads to the same conclusion: as long as humans are buying software from humans, you’d want to shift customer support, SDR, and implementation teams into “Customer Relations”. Putting most of their focus on learning more about the customer, their challenges, and their preferences. Knowing the humans involved and the systems they operate provides enormous leverage when you try to renew a contract, upsell a new product, or request a case study. Highly worth watching the interview on Lenny’s YouTube channel.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
3 minutes read.
This all leads to the same conclusion: as long as humans are buying software from humans, you’d want to shift customer support, SDR, and implementation teams into “Customer Relations”. Putting most of their focus on learning more about the customer, their challenges, and their preferences. Knowing the humans involved and the systems they operate provides enormous leverage when you try to renew a contract, upsell a new product, or request a case study. Highly worth watching the interview on Lenny’s YouTube channel.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Hi, I'm the Engineer That Built Out Vercel's First AI SDR Agent. AMA
3 minutes read.
Excellent AMA thread where people tried to go deeper into understanding why building it in-house versus buying a tool, what to consider when approaching it in your business, etc.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
3 minutes read.
Excellent AMA thread where people tried to go deeper into understanding why building it in-house versus buying a tool, what to consider when approaching it in your business, etc.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Peopleware
Revisiting Manager READMEs
5 minutes read.
You know that I’m a believer in individual READMEs. There is a reason I wrote one and created [https://managerreadme.com](http://managerreadme.com "") so we can all learn from each other. This can be an excellent tool for managers and for technical leaders who work with significant parts of the organization to deliver value. But that’s the point, it’s just a tool. Camille’s approach is also a solid one, moving from the individual’s preferences to the processes that the individual likes to operate the team - run the day to day, making decisions, etc. Pick the tools you believe will work for you and your team.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
5 minutes read.
You know that I’m a believer in individual READMEs. There is a reason I wrote one and created [https://managerreadme.com](http://managerreadme.com "") so we can all learn from each other. This can be an excellent tool for managers and for technical leaders who work with significant parts of the organization to deliver value. But that’s the point, it’s just a tool. Camille’s approach is also a solid one, moving from the individual’s preferences to the processes that the individual likes to operate the team - run the day to day, making decisions, etc. Pick the tools you believe will work for you and your team.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Lessons From Two Failed Promotions... And What Changed After ZIRP
4 minutes read.
Great tips to consider if you want to be promoted to the next level (IC or manager). Considering how to create visibility to your impact and vision is an area I don’t see enough people pay attention to. While people don’t like to brag, it’s arrogant to assume that people will see your work and be able to “live in your head” to imagine the type of vision you’re setting for the team. Talk more about it to create optionality both for yourself and for your teammates.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
4 minutes read.
Great tips to consider if you want to be promoted to the next level (IC or manager). Considering how to create visibility to your impact and vision is an area I don’t see enough people pay attention to. While people don’t like to brag, it’s arrogant to assume that people will see your work and be able to “live in your head” to imagine the type of vision you’re setting for the team. Talk more about it to create optionality both for yourself and for your teammates.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@disco_lu: Never send an LLM to do a linter's job. LLMs are comparably expensive and incredibly slow compared to traditional linters and formatters. We think you should always use deterministic tools whenever you can.
- 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.