Software Lead Weekly
Issue #703, 15th May 2026
This Week's Favorite
Flipping the Bozo Bit on Flips the Learning Off
4 minutes read.
"Cook and Woods note that our tendency to focus on differences between us and them when the incident happens to them leads us to miss aspects of the system that we actually have in common with them. By focusing on the differences, we miss the opportunity to learn from their experiences, because it seduces us into believing there’s nothing for us to learn here." -- This is true for the type of material you read and the people you learn from. If you ever care about your blind spots, search for those who are different than you. Talk with them, read their content, and educate yourself. Not for the sake of convincing or being convinced, but rather to learn another perspective and reason about it.
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4 minutes read.
"Cook and Woods note that our tendency to focus on differences between us and them when the incident happens to them leads us to miss aspects of the system that we actually have in common with them. By focusing on the differences, we miss the opportunity to learn from their experiences, because it seduces us into believing there’s nothing for us to learn here." -- This is true for the type of material you read and the people you learn from. If you ever care about your blind spots, search for those who are different than you. Talk with them, read their content, and educate yourself. Not for the sake of convincing or being convinced, but rather to learn another perspective and reason about it.
Read it later via Instapaper.
Share it via Twitter or email.
Culture
This Guy Used AI to Put Himself in Game of Thrones and Fix Everything
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.
Read it later via Instapaper.
Share it via Twitter or email.
Simple Sabotage Field Manual: The Most Effective Way to Destroy an Organization Is to Make It More Bureaucratic.
7 minutes read.
“the most effective way to destroy an organization is to make it more bureaucratic. [...] Physical sabotage could be discovered and repaired. But bureaucratic sabotage? It looked exactly like business as usual. [...] This gap between bureaucratic fantasy and human reality doesn't create efficiency—it creates exactly the kind of systematic dysfunction that wartime saboteurs learned to exploit. [...] I used to think this was a failure of leadership or organizational design. Now I wonder if it's simply physics—the inevitable entropy of human systems. Success breeds scale, scale breeds complexity, complexity breeds bureaucracy. The very mechanisms that protect large organizations from chaos also protect them from change. [...] What if AI could fill all those gaps, handling mechanical compliance while we focus on the human work?“ -- What an amazing take on a playbook from 1944 (WW2), with the US trying to slow down and harm the Nazi’s progress, and how much of it is true when looking at organization structure & processes today.
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7 minutes read.
“the most effective way to destroy an organization is to make it more bureaucratic. [...] Physical sabotage could be discovered and repaired. But bureaucratic sabotage? It looked exactly like business as usual. [...] This gap between bureaucratic fantasy and human reality doesn't create efficiency—it creates exactly the kind of systematic dysfunction that wartime saboteurs learned to exploit. [...] I used to think this was a failure of leadership or organizational design. Now I wonder if it's simply physics—the inevitable entropy of human systems. Success breeds scale, scale breeds complexity, complexity breeds bureaucracy. The very mechanisms that protect large organizations from chaos also protect them from change. [...] What if AI could fill all those gaps, handling mechanical compliance while we focus on the human work?“ -- What an amazing take on a playbook from 1944 (WW2), with the US trying to slow down and harm the Nazi’s progress, and how much of it is true when looking at organization structure & processes today.
Read it later via Instapaper.
Share it via Twitter or email.
No Pure Managers: Every Leader at Coinbase Must Also Be a Strong and Active Individual Contributor.
4 minutes read.
Many companies will find ways to justify layoffs in the name of AI. Operating a company today with AI is indeed very different from 3 years ago. I hope that many companies will find ways to pursue a sustainable path forward while seeking the truth rather than following trends. Less toil, less structure, less process, less overhead. All of that sounds like a dream for most of us. I'm on the side of Javon's Paradox, believing that the market will grow and new jobs will emerge, at least for people who can adjust and have agency over their careers.
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4 minutes read.
Many companies will find ways to justify layoffs in the name of AI. Operating a company today with AI is indeed very different from 3 years ago. I hope that many companies will find ways to pursue a sustainable path forward while seeking the truth rather than following trends. Less toil, less structure, less process, less overhead. All of that sounds like a dream for most of us. I'm on the side of Javon's Paradox, believing that the market will grow and new jobs will emerge, at least for people who can adjust and have agency over their careers.
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Sense of Urgency
3 minutes read.
Consistent "Sense of urgency" is often what moves companies from the p50 to the p75. It's not enough to drive excellence on its own; without it, it's impossible.
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3 minutes read.
Consistent "Sense of urgency" is often what moves companies from the p50 to the p75. It's not enough to drive excellence on its own; without it, it's impossible.
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
Software Is Eating the World (But Actually This Time)
7 minutes read.
If you love technology, these observations by Siddharth will get you excited for what's to come: "tokens per task = initial context + (number of steps × tokens per step). [...] This explosion is three curves compounding on top of each other: more users, more tasks per user being routed through models, and more tokens consumed per task as models can sustain longer, deeper workflows. If users double or triple, tasks per user also climb, and tokens per task rise again on top of that, total demand moves much faster than any one of those curves in isolation. [...] That is what inference demand really measures. More and more of the economy is being pulled onto the token ladder and executed as code. Software ate the world once by mediating business through screens. It may eat much more of it this time by doing the work underneath."
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7 minutes read.
If you love technology, these observations by Siddharth will get you excited for what's to come: "tokens per task = initial context + (number of steps × tokens per step). [...] This explosion is three curves compounding on top of each other: more users, more tasks per user being routed through models, and more tokens consumed per task as models can sustain longer, deeper workflows. If users double or triple, tasks per user also climb, and tokens per task rise again on top of that, total demand moves much faster than any one of those curves in isolation. [...] That is what inference demand really measures. More and more of the economy is being pulled onto the token ladder and executed as code. Software ate the world once by mediating business through screens. It may eat much more of it this time by doing the work underneath."
Read it later via Instapaper.
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How to Hire People Who Are Better Than You
9 minutes read.
This is a brilliant framing to ask yourself after the interview ends: "After the conversation, do you find yourself thinking: “Even if we don’t hire them, we’ve got to do half of the things they said.” Maybe you’re so excited you start working on it right away." -- Make sure to ask for the tradeoffs, the context required to make the decisions, and when to optimize for each scenario.
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9 minutes read.
This is a brilliant framing to ask yourself after the interview ends: "After the conversation, do you find yourself thinking: “Even if we don’t hire them, we’ve got to do half of the things they said.” Maybe you’re so excited you start working on it right away." -- Make sure to ask for the tradeoffs, the context required to make the decisions, and when to optimize for each scenario.
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@nikunj: Never trust (or listen) to anyone that gives advice in absolutes.. Not in this era. Not at this time. Everything is changing and rearranging so freaking quickly. Sure, some things are evergreen - focus on retention, run a good business and don’t commit fraud. But a lot of the old priors are turning out to be garbage aka don’t boil the ocean, do just one thing, figure out your wedge. PS: I’m sure someone will dig up one of my tweets where I have done this and fine, I was just wrong
@jasonlk: I've been doing this long enough to know there is no karma Folks do awful things and do just fine But I've also been doing this long enough to know if you are really, really good to a lot of people A few will really surprise you down the road and pay it back many times over
- 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.