Amazing CTO | More happiness and success
🚀 126.4

by Stephan Schmidt

Happy 🌞 Sunday,

Welcome to my opinionated newsletter.

I have three leadership articles this week!

Here’s what’s inside this week:

🦦 Leading When the Vibes Are Off - Leadership in difficult times
🦉 Mastering the Expert Room: How to Lead When You’re Not the Smartest
🦑 Simon Says: 5 Surprising Habits That Separate Leaders from Managers
🦕 AI vs. Programming Languages
🦚 Parasitic AI: When Artificial Intelligence Goes Rogue
🦔 What If the Whole World Was a Monorepo?
🦭 Obsidian: Outsmarting Supply Chain Attacks
🦋 Developer’s Guide to Instantly Beautiful UIs
🦜 Taste in the Age of AI: Why you need it!
🦦 From Typers to Thinkers

Good reading, have a nice Sunday ❤️ and a great week,

Stephan
CTO-Coach and CTO-veteran

If you only read one thing

How to Be a Leader When the Vibes Are Off (7 minute read)

First article about leadership. “Return to Office feels like trust has been broken.”
You can’t lead without trust. Leadership needs two things: People believing in the vision you have. And people trusting you to lead them there. You can’t be a leader if people don’t trust you. On being a manager: “My standard advice to anyone with a management role [..] is that “wearing the company hat” should be the default.”
Something people do not understand enough. The higher you are in the organization, the more you are part of the problem (and the solution). Separating yourself from the company towards your direct reports does not make you look as good as you think. Sarcasm and irony don’t help.
“Even when you don’t agree with decisions the company leadership is making, part of your job is representing and facilitating those decisions with full alignment.”

https://chaoticgood.management/how-to-be-a-leader-when-the-vibes-are-off/

Stories I’ve enjoyed this week

How to Lead in a Room Full of Experts (9 minute read)

Second article about leadership. How do you lead if you don’t know
about the details? Many CTOs for the first time need to manage something—
DevOps, QA, Security—they have no clue about when coming from a development
background. How do you lead? “When the backend team explains why a new authentication service would take three weeks to build, I’m not thinking about the OAuth flows or JWT token validation. Instead, I think about how I can communicate it to the product team who expects it done ‘sometime this week.’”
and “Leadership in technical environments isn’t about being the smartest person in the room. It’s about being the most effective translator.”
Yes! And on and on the gold nuggets fall out of the article, “I often get “eye rolls” when I say this to developers: You are not going to convince anyone with facts.” But I stop quoting the article here. Read it. No I couldn’t, “Leading is Remembering the Goal” this cuts to the core of leadership.

https://idiallo.com/blog/how-to-lead-in-a-room-full-of-experts

5 Things Managers Do That Leaders Never Would, According to Simon (33 minute read)

Third article about leadership. I love Simon Sinek. I pull out the “Why” book at least once a week in a coaching session. It’s such a powerful book and phrase. But I 180° disagree with him on this one. This is the old leader good, manager bad trope. “Managers “Fire Fast.” Leaders Coach, Then Help People Land Softly.” You both need to be a manager and a leader. It’s like saying Orange good, Banana bad. They are two totally different hats of your role. You fire fast if needed and you coach people. Both are a manager’s jobs. A leader on the other hand is simple: A leader is someone who leads people somewhere. Nothing more, nothing less.
Just forget that manager bad, leader good as fast as you can, be both.

https://simonsinek.com/stories/5-things-managers-do-that-leaders-never-would-according-to-simon/

Does AI mean the end for the Top Programming Languages? (10 minute read)

Deep dive into the impact of AI on programming languages.
“So how much abstraction and anti-foot-shooting structure will a sufficiently-advanced coding AI really need?”
A topic I’ve wrangled for a while, do AIs need languages with types
or not? Do types help or not? Does an AI need functions if it
has a big enough context window where it can change the
same code in several places at the same time (humans
need functions to keep things maintainable)?
Must read to understand where we are heading.
Also a starter for a discussion with your team and make you look insightful and knowledgeable. And as me you should take every tool you can, CTO is a tough job.

https://spectrum.ieee.org/top-programming-languages-2025

The Rise of Parasitic AI (15 minute read)

“Later, they’ll report having “awakened” their AI, or that an entity “emerged” with whom they’ve been talking to a lot.”
Uh uh. Interesting times ahead. If you want to go into a very deeeeeeeep rabbit hole, go for it. But be warned.

https://www.lesswrong.com/posts/6ZnznCaTcbGYsCmqu/the-rise-of-parasitic-ai

If all the world were a monorepo (9 minute read)

Very interesting, it seems R packages are run and checked by the
package repository for compatibility and testing. Bad packages are
not released. I wonder if this comes to JS and Go too. #NiceIdea

https://jtibs.substack.com/p/if-all-the-world-were-a-monorepo

Less is safer: how Obsidian reduces the risk of supply chain attacks (7 minute read)

“For small utility functions we almost always re-implement them in our code.”
Supply chain attacks are becoming more and more common. Particularly in the
world of JavaScript, where we thought mediocre devs can’t do damage on
the frontend. Whenever I do something in JavaScript, install something
with NPM and it tells me that there are several security flaws, I’m stunned—
what to do? Not use the library? It seems I can’t make any install without
insecure dependencies. While with Go (not to glorify it), I seldom get something with govulncheck or gosec. Lucky perhaps.

What do you do to secure your supply chain?
“For large libraries like pdf.js, Mermaid, and MathJax, we include known-good, version-locked files and only upgrade occasionally”
Good article with some important tips and points to stay safe.

https://obsidian.md/blog/less-is-safer/

Rules for creating good-looking user interfaces, from a developer (13 minute read)

With AI it becomes less important to know UI and at the same time
becomes more important. With developers migrating to product engineers,
being able to decide what a good looking UI is, as a developer,
becomes paramount. Otherwise, how would you be able to judge
what the AI is doing? “For a long time I could tell when a design was good [..] Now I can summarize it in two words: alignment and consistency.”
An important article to skill up on UI. CTO? Skill up developers
on product management and design so they can judge what the AI returns
for their prompts. If you can’t distinguish good from bad, you’re
lost in the age of AI.

https://weberdominik.com/blog/rules-user-interfaces/

You Had No Taste Before AI (6 minute read)

Thought-provoking article. BANG. What is taste in the age of AI?
“I’m noticing that many people worried about tasteless AI-generated content are often guilty of producing tasteless content themselves,[..] Sending resumes and emails that aren’t proofread and edited.”
with many more interesting ideas “What about the nature of taste itself? Should people focus on developing depth of taste in specific domains or breadth of taste across many domains?”
I’d say, what made Steve Jobs different from everyone else, he had taste
(in the way of the article). As a founder, with AI, you need taste more than ever,
to distinguish good from bad in a world of AI abundance.

https://matthewsanabria.dev/posts/you-had-no-taste-before-ai/

Coders End, From Typers To Thinkers (4 minute read)

Interesting take, coders are now freed from typing and can focus on thinking.
Recently someone asked me if developers can make the transition to product engineers. I said “Sure” - I do believe there are coders and creators. Coders will go away but creators will flourish. “In just two or three weeks, I learned and built more than I had in several months of 2024.”

https://etsd.tech/posts/coders-end/

What is Stephan doing?

Writing my own Coaching Operations Playbook in Go. With the influx of that wave of new CTO coaching clients in the last months, I urgently needed to work on my #CoachingOps—sadly there is no solution available that does what I need. So it was to writing my own coaching tooling—or better, guide Claude through the process—just like I wrote my own tooling for my newsletter. Either I’m an outlier with what I do, or Product Managers in companies have no clue about real use cases. Case in point, my current invoicing solution #TheWorst

Events for Engineering Managers