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🥯 Team Autonomy, Tech vs Architecture Debt, Negotiating Upwards, Employee Retention, Story Mapping: TMW #455

Legacy systems - what a CFO wants to hear...
🍍
Thanks to Build Circle for sponsoring this week’s issue of TMW - a technology consultancy that delivers business-critical technology platforms, scalable products, and AI-powered solutions to unlock the value of data and AI.

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

We're only a few weeks away from CTO Craft Con: The Finance Edition in London - if you're leading an engineering team in a fintech or financial services business, you don't want to miss it! See you there

How to Talk to CFOs About Legacy Systems...

A CTO Craft community member asked last week how CTOs effectively discuss investments, risks, and opportunities related to legacy systems with CFOs, seeking the specific vocabulary and framing that finance leaders appreciate and react to for better strategic alignment. Another member replied:

The messaging might be "Just keeping the lights on costs us $x + inflation, we're proposing a phased modernisation program which costs ($x + 20%) per year, for the next 2 years, then we'll see our costs drop to ($x - 50%) so we see a financial ROI in 3 years."

Solid advice!

Key takeaways from the discussion:

  • Quantify tech investments in clear financial costs and gains.
  • Frame legacy issues as a business case: highlight "cost of inaction".
  • Connect risk, resilience, and ROI to form a business continuity narrative.

And a thought exercise:
Considering a recent tech initiative, how might reframing its value as the "cost of not doing" or a direct business continuity improvement influence your pitch to a CFO?

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

Andy @ CTO Craft

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CTO Craft Con - Dates for Your Diary

CTO Craft Con: The Finance Edition
Join CTO Craft Con: The Finance Edition in 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: The Finance Edition 2025
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: London 2026
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: Toronto 2026

Reads of the Week

Councils of agents
Group thinking with LLMs.
The Engineering ManagerJames Stanier
Team Autonomy Is a Beautiful Lie — Here’s What’s Really Holding Teams Back | Lost Consultants
We celebrate “team autonomy” as a sign of modern, empowered work. But look closer — most teams are still on a leash. This post breaks down the illusion of autonomy and reveals what’s really holding teams back.
lostconsultants.comMaik Seyfert

Leadership, Strategy & Business

Making Technology Choices That Last
A practical guide to making better technology decisions
It Depends: Lessons in Technology LeadershipKevin Goldsmith
Negotiating With Your Boss
Especially one with an ego
Fish Food for ThoughtMike Fisher
Beyond the Cosmo Quiz: Using Assessments as Leadership Tools
A Conversation with Jen Fox and Suzan Bond
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Leadership Tip 23: How to Speak Truth to Power - Johanna Rothman
This is Johanna Rothman’s October 2025 Pragmatic Manager newsletter. The Unsubscribe link is at the bottom of this email. I happened to see a recent review of Practical Ways to Manage Yourself that made me laugh. (I don’t normally read book reviews because once I put the book out into the world, that book is […]
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Culture, People & Teams

How Managers Build (or Break) Their Team’s Confidence
As a manager, I’ve had reports who were struggling, despite my trying to set them up for success.
The Caring Techie NewsletterIrina Stanescu
Perkonomics report: Employee Retention Crisis | Perkbox
42% of UK workers feel undervalued. Discover how this perception gap is hurting retention—and how to close it with recognition and tailored benefits.
PerkboxSinead Murphy
You Can’t Just Flip the Switch on Empowerment
Most leaders try to flip from directive to empowered overnight. Here’s why it fails - and the deliberate path through coaching that works.
the Decision StackMartin Eriksson
The Funnel Is Dead: Hiring in the Age of AI - Organizational Physics
Summary Insight: The hiring funnel is dead. In an AI-saturated world, polish is cheap — proof is priceless. The winners won’t widen their funnels; they’ll invert them to test truth inside real work. Key Takeaways: AI destroyed résumé signals — competence must be observed, not claimed. Shift from screening for polish to testing for performance […]
Organizational PhysicsLex Sisney

Technology, Operations & Delivery

Drowning in an Oversized Product Backlog? Story Mapping Is Your Life Raft
Agile Pain ReliefMark Levison
Conductors to Orchestrators: The Future of Agentic Coding
From micro-manager to macro-manager: coding’s asynchronous future
ElevateAddy Osmani
Technical Debt vs. Architecture Debt: Don’t Confuse Them
Architecture debt silently sabotages AI, cloud and transformation initiatives. Learn the difference, how to diagnose those systemic issues and fix them.
The New StackNadzeya Stalbouskaya
AI’s Intersection with Trust
A look at Vanta’s 2025 State of Trust Report
Resilient CyberChris Hughes

Stress, Wellbeing & Growth

The Debugging of Geeta Sharma
She landed Google for $672,000. But before she said yes to the offer, she had to say one sentence she’d never spoken.
The Conscious LeaderTaha Hussain
How to Keep Winning
I’ve always been fiercely competitive. I enjoy everything about it—from training to get better, to building and developing teams, to the stress, pressure, and intensity. And while I love winning, the…
amasad.meFri Oct 24 2025
You Are How You Act
You are the sum of your behaviors not your intentions
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More Experience, More Overwhelmed
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That’s it!

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Have an amazing week!

Andy

Published by:

Andy Skipper