10 min read

🍉 Tech Coordination, Intuitive Leaders, Hiring Juniors, Progression Frameworks, Tech Debt at Scale, CI/CD Attacks: TMW #431

How safe is your team?
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Thanks to Buf for sponsoring this issue of TMW - store directly to Apache Iceberg tables and guarantee data quality with Bufstream, a drop-in replacement for Apache Kafka with broker-side schema awareness.

Hello, hello, hello - it's Monday!

As a technology leader, you should already know that psychological safety and trust are crucial for high-performing engineering teams. Google's Project Aristotle highlighted psychological safety as the most important dynamic of effective teams, meaning engineers must feel secure to voice concerns, question assumptions, and experiment - a necessity in complex and ever-changing software development. This allows for quicker problem identification, continuous improvement, and innovation; teams lacking this safety often play it safe, leading to missed opportunities and technical debt. Building this kind of environment requires strong leadership, including modelling vulnerability, active listening, and constructive responses to mistakes, emphasising blameless post-mortems, and celebrating calculated risks and those who challenge the status quo.

We collaborated with the brilliant Michelle McDaid to put together a vital guide to what trust means to the success of a team - you can see the article here, and we'll be chatting with Michelle live on July 10th to dig even deeper into the topic.

Have a great week! On with the links...

Andy @ CTO Craft

PS: Are you a member of the CTO Craft Slack community? If not, leave us your details here and we'll get you added - it's well worth it

It Starts With Trust: What Building Psychological Safety Really Means | CTO Craft
We Are a Good News Organisation “We are a good news organisation”“The senior leadership update is too negative – it needs to be reframed more positively”“Instead of focusing on risks, let’s talk about what we will deliver by when” You learn that if you question the approach, or highlight risks, you are labelled as negative or seen as someone who is not open to change. You try to raise concerns, but your voice is not heard. And some time later when there is a major outage, something you predicted would happen, you stay quiet. However, you feel resentful that you are the one who must work late to fix the problem you highlighted but weren’t listened to. The heat comes on your team who are blamed for ‘bad engineering’. There is no retrospective to reflect on learnings. Everyone is told this cannot happen again and reminded of the need to work harder, to move forward, faster. You learn that you either need to get on board or stay quiet. You realise it’s career suicide if you challenge. The next time you foresee an issue you don’t bother raising concerns – there’s no point. Have you ever experienced any of these scenarios? If you were CEO or a senior leader, would you want to hear the real story, or the sugar-coated version? If your proposed change is met with silence or you hear no objections, do you take this as agreement? There are many reasons for silence. One of them is a lack of psychological safety. Psychological Safety Amy Edmondson was surprised when her research found that the highest performing teams made more mistakes. It turned out that this was because they felt safe to admit their errors, whereas the lower performing teams felt the need to cover up their mistakes (Edmondson, 1999). Amy Edmondson defines psychological safety as “A belief that the team will not embarrass, reject or punish someone for speaking up with ideas, questions, concerns, or mistakes”. In a psychologically-safe workplace, people know that their voice is both welcomed and expected.” If you are working in a psychologically safe work environment you know that you won’t be punished for speaking up, sharing bad news, asking for support or admitting an error. You may find psychological safety in parts of an organisation but it could be absent in other pockets. In low trust work environments, people play it safe, keep their heads down, and stay silent. It’s hard to have innovation when people are keeping their heads down, and sadly these are words I am hearing a lot from people in tech! The Cost of Silence The pace of change in the technology industry requires a focus on continuous improvement and innovation. If employees don’t feel safe to share their ideas, innovation will be lacking. Why hire talented people but not hear from some of them? There are many reasons why people may not share their ideas. There may be a few loud voices of ‘experts’ that make others feel their idea is not good [...]

CTO Craft Events

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

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 10th JulyTime: 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:

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

Reads of the Week

Coordination Crisis in Modern Tech Work
Over 50% reported spending 25–50% of their week on “work about work”. What is the root cause of it? How can we improve that? Can AI help?
InfoQ Culture and Methods Trends Report - 2025
This report summarizes how the InfoQ Culture and Methods editorial team sees the ongoing and emergent trends in the culture and methods space.

From our Sponsors

Workshop: A deep dive into the technical underpinnings of Bufstream

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Join our interactive workshop on May 29: "Schema-Driven Governance for Streaming Data" for a deep dive into the technical underpinnings of Bufstream and the capabilities that become available when you understand the shape of your streaming data.

If you're interested in sponsoring TMW or any of our events, drop us a line at partners@ctocraft.com.

Leadership, Strategy & Business

On work processes and outcomes
Here’s a stylized model of work processes and outcomes. I’m going to call it “Model I”. Model I: Work process and outcomes If you do work the right way, that is, follow the 

The Welcome Back Doormat Technique
A completely made up name for a simple yet effective and rarely used technique to improve your effectiveness and impact. Low cost, high returns.
Dealing with Intuitive, Non-Strategists
Don’t Re-enact The Charge of the Light Brigade
Why leaders should trust their intuition
Leaders who balance their gut feelings with analytical thinking make faster, more authentic decisions, especially when navigating complexity in fast-paced environments.

Culture, People & Teams

AI Won’t Kill Junior Devs - But Your Hiring Strategy Might
No juniors today means no seniors tomorrow: rethinking talent development
To Get More Signal From Coding Interviews, Stop Saying This Word
And what to do instead
Using Social Drivers to Improve Software Engineering Team Performance
According to Lizzie Matusov, technical drivers like velocity offer an incomplete view of team performance. Social drivers—trust, autonomy, purpose, and psychological safety—provide a fuller picture and reveal important areas of opportunity for improvement. She spoke about the social drivers behind high-performing engineering teams at QCon San Francisco.
Merging Engineering Progression Frameworks
How to refresh or merge Engineering Progression Frameworks

Technology, Operations & Delivery

How Google Measures and Manages Tech Debt
Technical debt has haunted development teams for decades, yet remains surprisingly difficult to explain.
Compromising the Code: Inside CI/CD Pipeline Attacks
In today’s fast-paced development landscape, CI/CD (Continuous Integration and Continuous Deployment) pipelines are the backbone of modern

Unlocking high software engineering pace: Strictly limit work in progress
It seems counterintuitive, but having your engineering teams focus together on one thing at a time leads to stronger pace and better quality.
RDEL #91: What makes production incidents in GenAI services different from traditional cloud incidents?
GenAI incidents are detected later, mitigated more slowly, and rooted in deep infrastructure complexity.

Stress, Wellbeing & Growth

How To Create Meaningful Connections By Asking Great Questions
Note: We know this piece is a little longer than usual, so feel free to jump to the ‘Wrap-up and Takeaways’ section at the end. However, we believe you’ll find it to be an enjoyable read.There was a time, not so long ago, when curiosity felt like an impossible skill for me.I would sit in a conversation, racking my brain for anything I could say. The only options were to talk about myself - which felt awkward unless they’d asked - say a non sequitur, or come up with a question.But I felt so froze
Leader Impostor Syndrome
Some of the sharpest, most capable leaders I coach are walking around with a warped self-image. They don’t see themselves through a mirror—they’re squinting at an old, blurry Polaroid. A snapshot f

Why Writing Is the Best Tool for Personal Growth
Writing is the best thing you can do for your personal growth. See how to incorporate it at every step of personal experimentation.
Dealing with Burnout
Burnout isn’t failure. It’s a signal. Listen to it.

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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Have an amazing week!

Andy