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🤿 Creative Strategy, Storytelling Magic, Delegation, DevEx at Amazon, AI Enshittification, the Audience Effect, AI-driven PRDs: TMW #441

Fintech CTOs - come and join us in London in November!
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Thanks to Devin for sponsoring this week's issue of TMW - the first and best AI software engineer. Want to sponsor TMW?

Hello again, it's Monday!

The agenda for CTO Craft Con: The Finance Edition (London, Nov 18-19) is now live - and we couldn’t be more excited to share what’s in store: two days of honest conversations, practical insights, and connection with fellow tech leaders working at the intersection of finance and innovation.

CTO Craft Con: The Finance Edition
CTO Craft Con will bring together 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 London.
CTO Craft Con: The Finance Edition

From navigating compliance and GenAI to scaling platforms, we’re covering the good, the messy and everything in between. This one’s been shaped by our you, our community - and it’s full of real-world stories, peer-led discussions, and frameworks you can actually use. Check out the full agenda

On August 7th, we'll be sitting down with Michelle McDaid to chat about the importance of trust and psychological safety in engineering cultures - if you want to get some important insights into the implications and impact on a culture where employees fear speaking up, raising concerns, or admitting mistakes, you'll want to join Michelle and Emma that lunchtime. 

CTO Craft Bytes: It Starts with Trust - Fireside Chat with Michelle McDaid | CTO Craft
About the EVENT In this online Fireside Chat, Michelle McDaid and Emma Hopkinson-Spark go further into the subject of Michelle’s article on the CTO Craft blog around trust and psychological safety. Highlighting the critical importance of psychological safety in the workplace, particularly within the fast-paced technology industry, Michelle and Emma will look into the implications and impact on a culture where employees fear speaking up, raising concerns, or admitting mistakes. What the significant negative consequences, including stifled innovation, unaddressed risks leading to failures, and a lack of learning and improvement can mean for a business and their own experiences of both the positive and negative impacts where trust is at the heart of the workplace issues. What you’ll learn: A deeper understanding of psychological safety in a professional context, beyond the basic definition. The link between psychological safety and high-performing teams. Practical and actionable strategies for leaders and individuals to build and foster psychological safety within their teams and organisations. How to differentiate between healthy debate/disagreement and a lack of psychological safety that leads to silence. Methods for encouraging open communication and feedback, even when it involves critical perspectives or bad news. The importance of trust as a foundation for psychological safety and how to build and maintain trust within teams. The long-term benefits of investing in psychological safety for organisational success and employee well-being. key info Date: Thursday 7th AugustTime: 12:30pm – 1.30pmLocation: Online REGISTER NOW Speakers Michelle McDaid Founder, The Leading Place Emma Hopkinson-Spark NED & Coach @, CTO Craft REGISTER NOW Only open to CTOs and senior technology leaders. If you’re not sure if that’s you – please drop us a line. No recruiters. CTO Craft reserves the right to cancel tickets for ineligible ticket holders. MORE FROM CTO CRAFT:
CTO Craft

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
CTO Craft Con: The Finance Edition
CTO Craft Con will bring together 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 London.
CTO Craft Con: The Finance Edition

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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Reads of the Week

Going on the Offensive with Creative Strategy
Thoughts from Nudgestock 2025
MediumRoger Martin
Your Engineering Team Should be Looking to Solve Customer Problems
Build the RIGHT things first. Secondly, build the things RIGHT!
Engineering LeadershipGregor Ojstersek

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

Magic and Mouse House: How Storytelling Completes You as a Leader | CTO Craft
Explore how flexible work models in the tech industry defy the headlines about office returns. Key data from the CTO Compensation Report 2025
CTO CraftOskar Ficek
How to delegate while maintaining high standards
This is for managers who want to delegate AND maintain a high bar for quality of work. Here are the 5 tactics I learned over time that made delegating easier.
Wes Kao's NewsletterWes Kao
Moving from an orchestration-heavy to leadership-heavy management role.
For managers who have spent a long time reporting to a specific leader or working in an organization with well‑understood goals, it’s easy to develop skill gaps without realizing it. Usually this happens because those skills were not particularly important in the environment you grew up in. You may become extremely confident in your existing skills, enter a new organization that requires a different mix of competencies, and promptly fall on your face.
Irrational Exuberance
Five invisible disconnects that derail strategy (and how to fix them)
Even the most ambitious strategy won’t drive value if the execution is not aligned. When strategy and operations drift apart, organizations stall.
Management-Issues.comMolly Lebowitz

Culture, People & Teams

Failure to communicate | Another Rodeo
The Four Levels of Remote Communication, or Why Your Team Forgets Everything
Another Rodeo
Understanding and Leading Self-Organizing Teams - Mountain Goat Software
Learn what self-managing teams are, how leaders can guide without controlling, and the powerful outcomes that emerge from effective self-organization.
Mountain Goat SoftwareMike Cohn
Quantifying the Impact of Developer Experience: Amazon’s 15.9% Breakthrough | Amazon Web Services
AWS achieved a 15.9% year-over-year cost reduction by measuring the total economic cost of delivering software units rather than relying on traditional development productivity metrics.
Amazon Web Services
Building stronger engineering teams with aligned autonomy - Stack Overflow
Stack OverflowEira May
A Free Communication Self-Assessment for Your Team - Leadership Freak
Strong leaders energize conversations. Poor communication drains teams. Use this self-assessment to reflect on how your communication impacts the people around you. Even small adjustments can lift engagement, clarify expectations, and fuel forward momentum.
Leadership FreakDan Rockwell
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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

Where Is AI on the Enshittification Curve?
A Conversation with ChatGPT and Gemini About Job Losses from AI
O'Reilly MediaTim O’Reilly
Teamwork & XP in the era of Genies - Benji’s Blog
The pace of change for development teams feels higher than ever, and so XP’s tactics for helping teams embrace change are more helpful than ever.
Benji's Blog
RDEL #101: What can we learn from Meta’s code improvement practices?
Teams had over 20 attributes for code improvement prioritization criteria, with diverse origins for code improvement efforts. Reengineering efforts led to statistically significant improvements.
Research-Driven Engineering LeadershipLizzie Matusov
My Product Management Toolkit (67): Using AI to write a PRD
Writing Product Requirements Documents is one of the areas where ChatGPT or Claude can become your friend. You can save yourself a lot of precious time by using AI to turn rough product ideas into …
As I learn ...

Stress, Wellbeing & Growth

On agency
Or, how to handle being sentenced to freedom, and handle it effectively, and authentically, and responsibly
Escaping FlatlandHenrik Karlsson
The Audience Effect: Why We Change When Others Are Watching
The audience effect explains why we become different people when we know we’re being watched: the mere presence of others fundamentally changes what we choose to do and who we choose to be.
Ness LabsAnne-Laure Le Cunff
🎭 The Masked Singer of My Career
How embracing impostor syndrome helped me grow into a stronger, more honest version of myself — and how you can too.
MediumOren Yam

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

Interested in sponsoring TMW or any of our events? Check out some stats here

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