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đŸ”© Cool Heads, Speedy Decisions, Authoritarian Leaders, Accountability, Tech Debt Spends, Intellectual Self Doubt: TMW #440

Announcing the CTO Craft 100 awards - nominations open
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Thanks to Softwire for sponsoring this week's issue of TMW - exceptional digital solutions, built by award-winning talent. Want to sponsor TMW?

Hello again, it's Monday!

Big news: Nominations are now open for the CTO Craft 100 - Global!

We're celebrating the technology and engineering leaders shaping the future of our industry - from AI trailblazers to culture champions. This report will spotlight 100 influential figures from around the world, with insights into the challenges and innovations defining leadership in 2025. Nominate yourself, or someone you admire by 1st August 2025

Check out the CTO Craft 100 and make a nomination

We've been seeing some crazy growth in the CTO Craft Slack community, which has just passed 8,500 members, dotted all around the globe - a massive thank you to everyone who's joined the group, and for all your contributions and suggestions, but most of all for being there for each other. The community is absolutely the best, most supportive place to be for anyone leading software teams, and it's free to join - go take a look.

That's it, on with the links! See you next Monday

Andy @ CTO Craft

CTO Craft Con - coming soon!

CTO Craft Con: Berlin 2025
CTO Craft Con will bring together over 200 Chief Technology Officers and other senior technology leaders from the most exciting start-ups, scale-ups, unicorns, and big tech companies to elevate their engineering culture in Berlin
CTO Craft Con: Berlin 2025

Here are all the upcoming CTO Craft Con events, along with your exclusive access code for discounted subscriber tickets - see you soon

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Who are Softwire?

Softwire is a UK digital consultancy with real-world experience applying generative AI. They've run GenAI pilots, delivered production systems, and bring honest insight into what works, what doesn’t, and where the real value is. They’re here to share practical lessons, not hype, with the CTO Craft community. 

We partnered with Softwire in 2024 to create the Spilling the AI Tea report. If you haven't already seen it, grab some biscuits and download it right here

Download Spilling the AI Tea

Reads of the Week

How Engineering Leaders Stay Calm and Effective When It Gets Personal
6 real-world stories and the 4-step framework for resolving conflicts effectively!
Engineering LeadershipGregor Ojstersek
The Cool Head in a Crisis
Why great leaders grow calmer as the stakes rise
Fish Food for ThoughtMike Fisher

CTO Craft Mixers

It's a big week for Mixers! If you're in one of these cities, we'd love to see you - these are informal networking events, so come along, have a beverage and meet some of the community:

Want to meet other TMW subscribers and CTO Craft Community members in your city? See all upcoming Mixers in cities around the world here.

Leadership, Strategy & Business

The #1 Way to Speed Up Decision-Making - Organizational Physics
First Who, Then What Summary Insight: If your team is stuck in endless debate, the fastest way to regain momentum is to name who owns the decision. This one shift cuts through noise, reduces friction, and drives execution forward. Key Takeaways: Clarify decision ownership before debating what, how, or when. Push authority down to the [
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Organizational PhysicsLex Sisney
TBM 367: The Wicked “Big Picture” Loop
But a nagging doubt builds. The team is moving slowly. The views never change. Doubt grows. Or maybe a new strategy is emerging. Execs stop paying attention to these views. Meetings missed, etc. You learn that there’s back-channeling, and other meetings set up to get the “real story.” OKR cycles get missed or are rushed. Suddenly, you learn about new views emerging like the “just the tier 1 launches,” or “the engineering roadmap,” or ___________.
The Beautiful MessJohn Cutler
Leadership ≠ Control: How to Avoid the Authoritarian Spiral
The Dangerous Leadership Pattern Nobody Wants to Talk About
MediumKim Scott
Knowledge flows like heat
If you’re leading software-intensive product development without a software background, you’ve likely experienced the frustration of teams missing commitments despite clear expectations. You’ve defended delayed projects to executives, scrambled to reallocate resources, or watched initiatives stall f
LinkedInDirk Jan Swagerman

Culture, People & Teams

Accountability
From throat to choke to empowered ownership
JoTJeff
How to Deal With a Toxic Top-Performer
Every founder hires a brilliant jerk. They start as a dream hire, then turn into a cultural liability. Here’s how to fix it by shifting

MediumDave Bailey
C.A.M.P. Framework: Building Connection in Engineering Teams
Processes don’t ship great products. People do, and they do it when they trust each other. In my experience leading engineering teams

MediumBrian Olynyk
Don’t Just Eat and Complain: Why Engineering Culture Is Your Best Investment
“I can’t cook, but I can eat and complain” — that’s what my ex-girlfriend used to joke when we’d go to expensive restaurants and she

Beer And Servers Dont MixJoel Dickson
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Nominations are now open for the CTO Craft 100 - Global, our exciting new initiative celebrating the technology and engineering leaders who are courageously navigating today's complex landscape and shaping tomorrow's innovations. This isn't just a list; it's a vital spotlight on those driving real change and defining the future of tech.

Don't miss your chance to elevate the inspiring leaders you admire—nominate them today and help us celebrate the individuals propelling our industry forward before nominations close on August 1st, 2025!

Make your nominations today!

Technology, Operations & Delivery

“What’s the Ideal Percentage for Spending on Tech Debt?”
As humans, we struggle with uncertainty and complexity.
Maarten’s NewsletterMaarten’s Newsletter
Not So Fast: AI Coding Tools Can Actually Reduce Productivity
Study Shows That Even Experienced Developers Dramatically Overestimate Gains
Second ThoughtsSteve Newman
How to Measure the ROI of AI Coding Assistants
Pressure to adopt AI does not mean success. An AI strategy hinges on the ability to measure the impact of AI agents and coding assistants.
The New StackJennifer Riggins
What can agents actually do?
There’s a lot of excitement about what AI (specifically the latest wave of LLM-anchored AI) can do, and how AI-first companies are different from the prior generations of companies. There are a lot of important and real opportunities at hand, but I find that many of these conversations occur at such an abstract altitude that they border on meaningless. Sort of like saying that your company could be much better if you merely adopted more software. That’s certainly true, but it’s not a particularly helpful claim.
Irrational Exuberance

Stress, Wellbeing & Growth

Intellectual Self-Doubt: The Psychology Behind Questioning Your Competence
Intellectual self-doubt is a psychological pattern often associated with impostor syndrome where capable people question their competence.
Ness LabsAnne-Laure Le Cunff
Leading Is Emotionally Draining. Here’s How to Recover.
Emotional depletion is a real and significant tax of modern leadership. Recovery is no longer a luxury. Instead, it’s a leadership imperative, critical for protecting your well-being and sustaining your capacity to lead over the long haul. Three proven practices can help you process your emotions and replenish your energy after a challenging stretch: reflect, reframe, and restore. These steps don’t just help you reset in the short term; they also help you build the emotional muscle to handle future challenges with more steadiness and strength. Because your team doesn’t just need you today—they need you to last.
Harvard Business ReviewDina Denham Smith
Against “Brain Damage”
AI can help, or hurt, our thinking
One Useful ThingEthan Mollick
Hards Things First
Excellence is unlikely to happen if you don’t address the hard problems early in project execution. Habits for cultivating excellence won’t form unless you shed light on hard problems from the start. Excellence requires practice, and you need the team to work through the strenuous parts to build endurance. Psychologically speaking, teams build confidence in themselves when they solve the hard parts early. Self-efficacy enhances a team’s morale and attitude, creating a positive feedback loop that fosters high performance. Simply put, when you lead a team to confront challenging aspects, the team will cultivate the right habits for excellence, and their efficacy levels increase, ultimately leading to improved team performance.
because writing is clarifying

That’s it!

If you’d like to be considered for the free CTO Craft Community, fill in your details here, and we’ll be in touch!

https://ctocraft.com/community

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Please do remember to share this link if you know of anyone who’d like to receive TMW:

https://techmanagerweekly.com

Have an amazing week!

Andy

Published by:

Andy Skipper