🔭 Decision Stack, Fallible Systems, OWASP Updated, High Agency, Team Identities, Gossip, Enabling Constraints: TMW #456

Hello there, it's Monday, welcome to the week!

CTO Craft Con: The Finance Edition in London is next week - if you're leading an engineering team in a fintech or financial services business, you don't want to miss it! See you there

Navigating Mental Health and Business Flow

Last week, community members explored strategies for sustaining business momentum when facing mental health challenges, prompting community insights on self-care, professional support, and adapting expectations.

"Think of yourself as a resource; you only have so much to give."

Key takeaways from the conversation:

• Accept mental health as a valid, fluctuating resource.
• Explore professional therapy for emotional backing.
• During lows, focus on micro-tasks and adjust expectations.

And a thought exercise:
Reflect on how reframing productivity expectations during mental health dips can shift internal states from guilt to self-compassion.

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

Andy @ CTO Craft

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Reads of the Week

The Decision Stack in Action: How Fujifilm Survived What Killed Kodak

A case study in how clarity across every level of decision-making determines survival in technological disruption

the Decision StackMartin Eriksson

Leadership, Strategy & Business

“Good engineering management” is a fad

As I get older, I increasingly think about whether I’m spending my time the right way to advance my career and my life. This is also a question that your company asks about you every performance cycle: is this engineering manager spending their time effectively to advance the company or their organization? Confusingly, in my experience, answering these nominally similar questions has surprisingly little in common. This piece spends some time exploring both questions in the particularly odd moment we live in today, where managers are being told they’ve spent the last decade doing the wrong things, and need to engage with a new model of engineering management in order to be valued by the latest iteration of the industry.

Irrational Exuberance

Become the Consequence

I am of the opinion that when you start a new role, not a new job, a new role that you have not done before, it requires a minimum of three years to become good or competent at that role. This window of acclimation grows with the complexity of the role. I’d suggest that while you’ll be a good manag

Rands in ReposeName *

If Your System Never Fails, That’s the Real Failure

Investments in operations should be at a minimal level that maintains the systems in an acceptable state forever. Poor operations are clearly bad news. But perfect operations are a waste of money.

Scarlet InkDave Anderson

How to be “high agency” at work

Practical examples of how to “just do things” when others are stuck overanalyzing and procrastinating — incl. how to leverage AI

The Operator's HandbookTorsten Walbaum

Culture, People & Teams

Using team identity to build success

ALSO: ‘it’s not a you problem, it’s a we problem’

Make Work BetterBruce Daisley

Training junior engineers

Make them do stuff and keep them in productive struggle mode

Nuts and BoltsNatasha Jaffe

The Unspoken Pact: How Conflict Avoidance Quietly Wrecks Team Dynamics

Conflict avoidance and polite silence can destroy healthy team dynamics. Here’s how to recognize the unspoken pact—and what to say instead.

Let's Grow LeadersKarin Hurt and David Dye

The Meeting After the Meeting: Where Genies Go to Gossip

The dangers of the meeting after the meeting and what to do instead. Practical communication tips for more candid conversations.

Let's Grow LeadersKarin Hurt and David Dye

Technology, Operations & Delivery

The OWASP Top 10 Gets Modernized

A look at the 2025 update to the OWASP Top 10, the most significant update since 2021

Resilient CyberChris Hughes

TBM 386: Understanding Enabling Constraints Using Shape Up (Basecamp)

After reviewing dozens (hundreds?) of operating systems in depth, I’m becoming increasingly convinced that the thoughtful design and deployment of constraints is a superpower.

The Beautiful MessJohn Cutler

Revealing the unknown unknowns in your software - Stack Overflow

Stack OverflowPhoebe Sajor

Why building for the 20% leave the rest behind

The core user trap and how optimization can kill Inclusivity

Effective Software LeadsJames Samuel

Stress, Wellbeing & Growth

Strategic Optimism

Many senior leaders view themselves as “realists.” But this so-called realism is often just cynicism in a suit. Being optimistic doesn’t mean being naive. It’s a strategic advantage for those aimin…

Aviv Ben-Yosef

The Psychology Of Rebranding Yourself- rebuilding your identity after a burnout

“ Maybe you are not lost. Maybe you just outgrow the person you used to be.”

MediumRiya Thakore

Thinking Clearly

If you have ever met me in person, you know that when you share an idea with me, I simplify it to its core and reflect it back to you, focusing on its essential parts. I dissect each statement for precision. “What do you mean by this word?” I have two decades of experience working … Continue reading Thinking Clearly

Daniel Lemire's blogView all posts by Daniel Lemire

Take Weird Ideas Seriously

Weird Ideas as Individual Alpha and Societal Necessity

Not Boring by Packy McCormickPacky McCormick

That’s it!

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Have an amazing week!

Andy