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🦤 Project Failures, IC Manager Pendulum, Board Meetings, Culture Change, Slowing Development, Articulate Yourself: TMW #459

Getting AI prototypes to scale is tough - join us on Dec 9th to learn how to survive it
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Massive thanks to Sonar for sponsoring this week's issue - the independent standard for integrated code quality and security.

Hello, hello, hello! Welcome to the week

Our recent Mind the Gap: Bridging from Sandbox to Scale survey and the report based on the findings we gathered is an important read for any technology leader right now. It's very clear that while AI tools are being commoditised at such a fast rate and we're capitalising on that to create proofs-of-concept that are powerful and intelligent, taking them out of the experimental stage and making them production ready is still a challenge that we haven't quite resolved.

Next week on December 9th, we'll be joined by our friends at Ten10 and The Scale Factory to dig further into the report's findings, as well as some common patterns for surviving the leap from prototype to production. It's free to join, and I guarantee you'll come away with useful insight and tools to use - check it out.

CTO Craft Bytes: Mind the Gap: Why Two-Thirds of AI Projects Never Reach Production | CTO Craft
We’re excited to invite you back to a new edition of our online series, CTO Craft Bytes: Mind the Gap, where we dig into what stops most AI initiatives from ever landing in production — and what you, as a senior tech leader, can do about it.

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

Andy @ CTO Craft

CTO Craft Con - Dates for Your Diary

CTO Craft Con: London
Join CTO Craft Con: London - an intimate, community-centered gathering for engineering leaders to connect, learn through insightful sessions, and build real peer relationships in a supportive environment.
CTO Craft Con: Toronto
Join CTO Craft Con: Toronto- an intimate, community-centered gathering for engineering leaders to connect, learn through insightful sessions, and build real peer relationships in a supportive environment.
CTO Craft Con: Europe | CTO Craft
CTO Craft Con: Europe 2026 Be the first to know CTO Craft Con: Europe arrives in Amsterdam, 29-30 September, 2026. Two days of real conversations, practical sessions, and peer connections designed for technology leaders across the continent. Register your interest today to get early updates, first access to tickets, and the latest speaker announcements. Register Your interest
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The AI Productivity Paradox

AI promises to speed up coding, yet many organisations aren’t realising the productivity boost they expected. Faster code generation often introduces new quality issues, shifting the bottleneck to the review process—an AI engineering productivity paradox.

On 10 December in London, Sonar will host a roundtable to explore why this happens and how to overcome it, examining LLM capabilities, developer workflows, and risk management for AI-generated code. Join your peers for an in-depth, data-driven discussion.

Join the State of Code VIP Roundtables

Andy's Read of the Week

Trillions Spent and Big Software Projects Are Still Failing

This article reveals the persistent problem that large-scale technology projects continue to fail at the same rate they did two decades ago, despite massive investments in new software tools and development methodologies. It suggests that the root cause of these failures is often not a technical deficiency, but rather fundamental issues in technology management, such as inadequate change management, poor leadership, and organisational misalignment.

Why should we pay attention as tech leaders? Because this article shifts the focus from technical solutions to organisational strategy. Go on, have a read.

Leadership, Strategy & Business

The engineer–manager pendulum is breaking
The hybrid era of engineering leadership is here, and the traditional IC/manager model is no longer suitable.
Spark joy, throw everything out
A few weeks ago I was visiting some family in Guelph. After, I went for a short bike ride in the evening. I found myself at a Little Library in a corner of the city that I hadn’t explored before. Inside it, I found Spark Joy, a book by
What Really Happens in a Board Meeting
Demystifying Board Meetings: A CTO’s Perspective
ICs vs Managers vs Leaders: Why Real Leadership is Rare
It should be considered that there is nothing more difficult to handle, more doubtful of success, or more dangerous to carry through than to initiate a new order of things. For the innovator makes enemies of all those who prosper by the old order while only lukewarm support is forthcoming

Culture, People & Teams

Want to Invite Culture Change? Combine Metrics and Stories, Part 1 - Johanna Rothman
This is Johanna Rothman’s November 2025 Pragmatic Manager newsletter. The Unsubscribe link is at the bottom of this email. I’ve been working with Stephanie, a senior leader who’s trying to nudge her organization to more organizational agility. Not because agility is so “good,” but because they want to quickly launch new products and new versions […]
Pre-Mortem Block By Leadership? Age-of-Product.com
What Organizational Dysfunctions Are Revealed When the Leadership Blocks Your Pre-Mortem — Age-of-Product.com
TBM 391: You’re Not Misaligned. You’re Thinking Differently.
I’ve been thinking a lot about why some people are wired for concrete solution-thinking while others naturally gravitate toward more abstract, problem-focused, or strategy-level thinking.
Team dynamics framework | Andi Roberts - Executive Coach | Leadership Trainer | Facilitator
The Team Dynamics Model is a team performance construct grounded in recent research that allows teams to build, maintain and raise performance
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Mind the Gap: Bridging from Sandbox to Scale

For senior tech leaders, the challenge isn’t proving AI’s potential; it’s scaling it responsibly. Mind the Gap: Bridging from Sandbox to Scale reveals the hidden organisational and governance barriers that keep promising projects stuck in pilot mode. Explore data-backed insights and proven strategies to help your teams turn experimentation into real, production-ready impact.

Learn how to take AI experiments into Production - Free Report

Technology, Operations & Delivery

Why Does Development Slow?
It’s the options
Putting Spec Kit Through Its Paces: Radical Idea or Reinvented Waterfall?
Spec-Driven Development promises reliable, specification-led software generation, but in practice I found the workflow slow, heavy, and less effective than iterative prompting. This post walks through a real-world test using Spec Kit and explains why traditional AI-assisted development still outpaces SDD by a wide margin.
The tech debt elephant: A product perspective
Maximise your product’s chances of success by balancing tech debt and architectural improvements: tips from a product manager.
Five Hard Lessons from Recovering a Catastrophic Microservices Migration
At QCon San Francisco, HeartFlow’s VP of engineering, Sonya Natanzon, shared lessons from navigating a recovery process after inheriting a catastrophic identity migration that locked users out of a healthcare portal on day one. Her five hard-won lessons reveal that successful architectural recovery depends as much on perception management and team dynamics as on technical prowess.

Stress, Wellbeing & Growth

How to articulate yourself intelligently
The inner album of greatest hits, and 3 frameworks to practice with
The Success Trap
How winning can shrink your options
Why Are You Productive For “Only” 5-6 Hours Each Day?
Almost no one is productive for 8 hours a day straight! Learn why and how to think about your daily productivity differently.
The Math of Why You Can’t Focus at Work
Interruptions, recovery time, and task size: three numbers that determine if you’ll get real work done. Interactive visualizations show the math behind bad days.

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!

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