Software Lead Weekly
Issue #700, 24th April 2026
This Week's Favorite
The Friction Is Your Judgment (Video)
18 minutes read.
It feels the end goal (3-year horizon) we all look at is to create products that can build themselves (including PM work) while we guarantee that customers' value is delivered and improved over time. "The Trap" (4:32 in) captures well the problems of 2026, as companies (well, the non-LLM companies) are figuring out how to build the right tools and harness them to achieve that. "Entropy is self-reinforcing" is the best framing I took from this talk for the current way of building software.
Read it later via Instapaper.
Share it via Twitter or email.
18 minutes read.
It feels the end goal (3-year horizon) we all look at is to create products that can build themselves (including PM work) while we guarantee that customers' value is delivered and improved over time. "The Trap" (4:32 in) captures well the problems of 2026, as companies (well, the non-LLM companies) are figuring out how to build the right tools and harness them to achieve that. "Entropy is self-reinforcing" is the best framing I took from this talk for the current way of building software.
Read it later via Instapaper.
Share it via Twitter or email.
Culture
Modern Friends
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.
Dropping Sprints: A Year With Shape Up
12 minutes read.
If you've worked with me, you know I say that all processes are terrible, but under certain constraints and optimization factors, some of them are useful. Read this post as is. In today's age of agentic development, experimenting with different ways of work is critical.
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12 minutes read.
If you've worked with me, you know I say that all processes are terrible, but under certain constraints and optimization factors, some of them are useful. Read this post as is. In today's age of agentic development, experimenting with different ways of work is critical.
Read it later via Instapaper.
Share it via Twitter or email.
What Happens When You Tell a Thousand People to Build With AI
10 minutes read.
Ramp is an amazing company in terms of execution speed, maybe that explains it: "Ramp has always been an impatient company. Allergic to inefficiency. Curious about new tools. The kind of place where people try things without asking permission, which occasionally creates chaos but mostly creates velocity. [...] Builders at Ramp expect to rebuild. Trainers expect to retrain. Managers expect to re-scope. Users expect to migrate when a new demo drops. The tools we're running right now? We genuinely hope they're obsolete by June. From the outside, this looks chaotic. From the inside, it's the opposite. People aren't attached to their tools. They're attached to their problems. When a better way to solve the problem shows up, they grab it." -- Check the AI Power curve, I think it's spot on.
Read it later via Instapaper.
Share it via Twitter or email.
10 minutes read.
Ramp is an amazing company in terms of execution speed, maybe that explains it: "Ramp has always been an impatient company. Allergic to inefficiency. Curious about new tools. The kind of place where people try things without asking permission, which occasionally creates chaos but mostly creates velocity. [...] Builders at Ramp expect to rebuild. Trainers expect to retrain. Managers expect to re-scope. Users expect to migrate when a new demo drops. The tools we're running right now? We genuinely hope they're obsolete by June. From the outside, this looks chaotic. From the inside, it's the opposite. People aren't attached to their tools. They're attached to their problems. When a better way to solve the problem shows up, they grab it." -- Check the AI Power curve, I think it's spot on.
Read it later via Instapaper.
Share it via Twitter or email.
The AI Inventory Trap: Why Faster Upstream Makes You Slower End-to-End
8 minutes read.
If you didn't see the impact on your ability to ship value faster to your customers, read this post. Theory of constraints analysis can be helpful to understand if you can accelerate and sustain deliverables: "This points to a harder truth: AI amplifies whatever system it’s dropped into. In a system optimized for finishing, AI multiplies proven impact. In a system with long cycles and high WIP, inventory multiplies. The technology is the same; the system design determines the sign."
Read it later via Instapaper.
Share it via Twitter or email.
8 minutes read.
If you didn't see the impact on your ability to ship value faster to your customers, read this post. Theory of constraints analysis can be helpful to understand if you can accelerate and sustain deliverables: "This points to a harder truth: AI amplifies whatever system it’s dropped into. In a system optimized for finishing, AI multiplies proven impact. In a system with long cycles and high WIP, inventory multiplies. The technology is the same; the system design determines the sign."
Read it later via Instapaper.
Share it via Twitter or email.
Peopleware
Product Strategy Still Means Saying No.
4 minutes read.
This is the insight more teams should adopt to leverage the new technological leverage: "That [AI] changes opportunity cost too. It used to be the cost of taking capacity away from the obvious priority. Increasingly, it is the cost of not pursuing the more ambitious idea now that it is finally within reach. So yes, product strategy still means saying no. But teams that keep operating with the instincts of a scarcer era will miss the shift. The question is no longer just what to cut. It is where to go deeper, move faster, and be more ambitious because the executional constraints have changed."
Read it later via Instapaper.
Share it via Twitter or email.
4 minutes read.
This is the insight more teams should adopt to leverage the new technological leverage: "That [AI] changes opportunity cost too. It used to be the cost of taking capacity away from the obvious priority. Increasingly, it is the cost of not pursuing the more ambitious idea now that it is finally within reach. So yes, product strategy still means saying no. But teams that keep operating with the instincts of a scarcer era will miss the shift. The question is no longer just what to cut. It is where to go deeper, move faster, and be more ambitious because the executional constraints have changed."
Read it later via Instapaper.
Share it via Twitter or email.
There's One Question I Ask Every Founder, and It's Not About Market Size, Their Team, or Their Model.
3 minutes read.
Questions about moat or unfair advantage can help the team identify where they think they can innovate. There can be other answers that are extremely hard to replicate, but very few seek them. It's easier to think that your product and technological capabilities will save you. This era is over (if it ever existed.)
Read it later via Instapaper.
Share it via Twitter or email.
3 minutes read.
Questions about moat or unfair advantage can help the team identify where they think they can innovate. There can be other answers that are extremely hard to replicate, but very few seek them. It's easier to think that your product and technological capabilities will save you. This era is over (if it ever existed.)
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@andrewchen: The biggest and most productive people in the AI era are the folks who are already good at their jobs. AI as a multiplier, not an equalizer/democratizer
@BowTiedTrance: Scott Adams: "This is one of the best reframes I've ever used." Focus on curiosity, instead of focusing on the problem.
- 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.