Software Lead Weekly
Issue #649, 2nd May 2025
This Week's Favorite
Finding Your Thing's Essence
8 minutes read.
"If you’re a builder, a founder, or just someone who’s ever tried to explain an idea that doesn’t quite fit in a box, this [post] one’s for you." -- Alex Dobrenko shares the struggles of defining and iterating on creating clarity around the product. I love this type of blog post, as you can feel the pains and drive a lot of inspiration from their methods (e.g. Project Essence) and artifacts.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
8 minutes read.
"If you’re a builder, a founder, or just someone who’s ever tried to explain an idea that doesn’t quite fit in a box, this [post] one’s for you." -- Alex Dobrenko shares the struggles of defining and iterating on creating clarity around the product. I love this type of blog post, as you can feel the pains and drive a lot of inspiration from their methods (e.g. Project Essence) and artifacts.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Culture
Just Finished My New Floor Heating.
1 minutes read.
My humble effort to help you start the weekend with a smile on your face.
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 on your face.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Jeeps, Ferraris, and Other Engineers
6 minutes read.
Looking at the preferences and strengths of individuals in your team will shed some light on how to put them in a better position to be successful, and see if they want to learn different ways to operate: "One way to view Jeeps vs. Ferraris is that they represent the dichotomy between robustness and speed. Jeeps exemplify robustness (but do not go very fast); Ferraris exemplify speed (but are fragile). Another lens is that Jeeps can handle 10x breadth while Ferraris can handle 10x depth."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
6 minutes read.
Looking at the preferences and strengths of individuals in your team will shed some light on how to put them in a better position to be successful, and see if they want to learn different ways to operate: "One way to view Jeeps vs. Ferraris is that they represent the dichotomy between robustness and speed. Jeeps exemplify robustness (but do not go very fast); Ferraris exemplify speed (but are fragile). Another lens is that Jeeps can handle 10x breadth while Ferraris can handle 10x depth."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
"How Do You Learn to Run a Company?" A Brilliant 2-Minute Answer by Steve Jobs About Asking Questions. (Video)
2 minutes read.
People (most of them) become lazy when systems are not good enough, and information and controls are lacking. You end up with some "rounding errors" that are even worse than the math (e.g., margins calculation) as they influence behaviors. People accept it long enough, then "overnight," making it a norm.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
2 minutes read.
People (most of them) become lazy when systems are not good enough, and information and controls are lacking. You end up with some "rounding errors" that are even worse than the math (e.g., margins calculation) as they influence behaviors. People accept it long enough, then "overnight," making it a norm.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Your Beliefs Are Your Strategy
6 minutes read.
What a beautiful idea. Writing a manifesto as a leader while starting first (as needed!) on the users (can be internal or external) you serve: "A good manifesto puts the person you serve and what they’re trying to get done in the center of the frame. And it proves you've done the work to be able to read their mind — or exposes the fact that you have to get a lot closer to their daily life, their list of projects, and the pressures they're carrying before you're ready to build something meaningful."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
6 minutes read.
What a beautiful idea. Writing a manifesto as a leader while starting first (as needed!) on the users (can be internal or external) you serve: "A good manifesto puts the person you serve and what they’re trying to get done in the center of the frame. And it proves you've done the work to be able to read their mind — or exposes the fact that you have to get a lot closer to their daily life, their list of projects, and the pressures they're carrying before you're ready to build something meaningful."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Peopleware
Be Less Scared of Overconfidence
8 minutes read.
This. A thousand times this: "The problem is that the bad consequences of underconfidence and under-ambition are severe but subtle, whereas the bad consequences of overconfidence and wishful thinking are milder but more obvious. If you’re overconfident, you’ll try things that fail, and people will laugh at you. If you’re underconfident, you’ll avoid making risky bets, and miss out on the potential upside, but nobody will know for sure what you missed. That means it’s always tempting to do what the low-info heuristic tells you and be less ambitious—but ultimately, that ends up being worse for the world."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
8 minutes read.
This. A thousand times this: "The problem is that the bad consequences of underconfidence and under-ambition are severe but subtle, whereas the bad consequences of overconfidence and wishful thinking are milder but more obvious. If you’re overconfident, you’ll try things that fail, and people will laugh at you. If you’re underconfident, you’ll avoid making risky bets, and miss out on the potential upside, but nobody will know for sure what you missed. That means it’s always tempting to do what the low-info heuristic tells you and be less ambitious—but ultimately, that ends up being worse for the world."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
The Chief Architect Role — Part 3 (Who I Work With)
5 minutes read.
"That being the case, most of my work, the Chief Architect’s work, is in making sure this entire thing that we call a product offering, the systems that comprise it, make sense. How do we do that? Well, mainly by getting as broad as a perspective as possible and by the delicate act of steering, which I’ll touch on a bit later. How do we get the needed perspective? by interacting with the various stakeholders in the company." -- The exact role in each company is slightly different, so getting some perspective and insights is helpful if you consider taking such a role in your career.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
5 minutes read.
"That being the case, most of my work, the Chief Architect’s work, is in making sure this entire thing that we call a product offering, the systems that comprise it, make sense. How do we do that? Well, mainly by getting as broad as a perspective as possible and by the delicate act of steering, which I’ll touch on a bit later. How do we get the needed perspective? by interacting with the various stakeholders in the company." -- The exact role in each company is slightly different, so getting some perspective and insights is helpful if you consider taking such a role in your career.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Building Leadership Influence by Asking the Right Questions First
4 minutes read.
Allison McMillan shares a short and helpful way to map out communication and context given the audience. Download the 2 PDFs and try it out. Creating visibility with different leadership layers often increases optionality, sending more impactful efforts and projects your way.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
4 minutes read.
Allison McMillan shares a short and helpful way to map out communication and context given the audience. Download the 2 PDFs and try it out. Creating visibility with different leadership layers often increases optionality, sending more impactful efforts and projects your way.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@Suhail: In 18 mo or so, 30% of design will also be done by AI. It is inevitable. Taste will matter more than ever.
@AdamTornhill: AI accelerates coding, but it can decelerate thinking. Effortless isn’t effective when it comes to learning.
- 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.