🫐 Storytelling, Measuring Judgment, Building Influence, Alignment vs Autonomy, PIPs vs IDPs, Should QA Exist?: TMW #475

Hello, hello, hello, welcome to the week!

"The Joy Has Gone Out of the Work."

This week, one of our members asked a question that clearly struck a nerve: how do you hold a team together when AI is doing more and more of the work? What followed was exactly the kind of conversation that makes this community worth being part of: honest, experienced voices sharing hard-won perspectives on one of the most pressing leadership challenges of the moment. A developer had told their CTO something quietly alarming in a 1:1: the joy had gone out of the work. Too much AI, not enough human connection, and a creeping anxiety about what it all means for the future.

The discussion that unfolded was full of the kind of practical wisdom you simply don't find in blog posts or LinkedIn hot-takes - opt-in Slack huddles that recreate the ambient hum of an office, mob programming as a vehicle for rebuilding team bonds, lessons drawn from HashiCorp's remote working playbook, and a frank discussion about what it actually feels like to lead through disruption with no clear map. Nobody had all the answers, but that's really the point. The best thinking happens in rooms where people feel safe enough to say I don't know.

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Our recent survey with Damilah looked at how leaders in 2026 perceive how the role will change by 2028, what will be expected of us and our teams, and how to prepare for those changes. We'll be sitting down with the Damilah team in London on May 7th to dig into some of the findings - it's free to attend, so do come if you'd like to see what we discovered:

CTO Craft Bytes: Engineering 2028: A Leadership Masterclass | CTO Craft

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That's it, let's look at some links....

Andy @ CTO Craft

From Coder to Orchestrator | CTO Craft

The definition of a senior engineer is changing. Explore how AI is shifting the premium from technical execution to orchestration and intent.

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Reads of the Week

Technical leaders make these 3 common storytelling mistakes

Anytime you feel the urge to say, “Well, technically…,” you’re about to kill a good story.

Wes Kao's NewsletterWes Kao

% You Can Quantify Cost. Here Are Four Ways to Measure Judgment.

AI made building cheap. Judgment is the new differentiator. Here’s a 4-part rubric to make product taste visible, scorable, and teachable.

Jeff GothelfJeff Gothelf

Leadership, Strategy & Business

Managing What You Cannot See: Why Your Dashboard Is Lying

Most leaders think they manage execution. They manage invisible friction instead. Here’s how individual signals become a governance system — and who owns it.

The Socratic LeadershipPetros Bountis

Communication Failure That Almost Cost Me My Job

And what it taught me

High-Impact EngineeringRoman Nikolaev

The Alignment Tax: What a Real CTO Relationship Looks Like vs. a Fake One

And how it sets the temperature for the entire organization.

InsideProductOrgStephanie

How Senior Leaders Can Build Their Influence

You propose a strategic shift. The case is solid, the logic sound. But weeks later, nothing moves. You advocate for a technology investment and get polite nods, then silence. You’re in the upper ranks of your organization with a track record of good judgment, but you can’t get people to act. The problem isn’t always your idea. It’s that getting traction at this level requires more than a strong argument. Here’s how to build your influence and get buy-in from stakeholders.

Harvard Business ReviewRebecca Knight

Culture, People & Teams

Autonomy Is Overrated: Why Alignment Beats Autonomy

(Enabling) Constraints: Why the Spotify Model Failed

Maarten’s NewsletterMaarten Dalmijn

What about juniors? - Marc’s Blog

Marc's BlogMarc Brooker

PIP vs IDP - Exit or Growth - Yaniv Preiss

PIP and IDP are two distinct tools used by managers for different purposes.

Yaniv PreissYaniv Preiss

Most 1:1s are run the wrong way

Guide for Managers: How to run 1:1s

Productify by BandanBandan Singh

Technology, Operations & Delivery

Should QA exist | Jade Rubick - Engineering Leadership

There are a lot of challenges in the way QA and engineering work together. Many eng leaders think you shouldn’t have QA. I dig in.

Jade Rubick - Engineering LeadershipJade Rubick

The Real Bottleneck in Engineering: Why AI Didn’t Fix What Slows Teams Down

AI made execution faster, but decision-making, alignment, and validation are still limiting performance. Here’s where engineering teams actually lose time.

The Engineering TaxAlvaro Lorente

2026 Staff Engineers Need to Get Hands-On Again

Hi, I’m Paula Muldoon – a staff software in multimodal GenAI at Zopa Bank in London. Review season is over and if you’re like me, you’re having the usual existential crisis …

Paula MuldoonFiddlersCode

Working on products people hate

Stress, Wellbeing & Growth

Ethos: The Art of Building Trust and Credibility

In leadership, your persuasiveness is contingent upon one question people are always asking: Can I trust the person behind the message? That’s the key idea behind the ancient Greek concept of Ethos. Originally meaning “habitat” or “character,” Aristotle considered ethos, or the appeal to credibility, as the “first among

Leading SapiensSheril Mathews

The Human Cost of Hard Leadership

You are three hours into back-to-back meetings, the third escalation email of the day just arrived, and someone on your team missed a deadline again.

Eva’s SubstackEva Selhub, MD

Ness Letters: Rebuilding Motivation - Ness Labs

You built the to-do list. You made the coffee. You opened the doc. And then you just… didn’t do the work. For three hours. Some days, you wake up energized and ready to start work. Other days, even the projects you care about feel strangely heavy. You stare at your screen, knowing exactly what you ... Read More

Ness Labs

What Burnout Actually Is

And what it definitely isn’t — because confusion about this costs people years

Health & Wellness CoachHealth Coach | Husam

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Have an amazing week!

Andy