🐌 Is AI Okay?, Chasing Strategy Squirrels, Stakeholder Comms, Non-Project Backlogs, Flaky Tests, The Dollar Cost of Burnout: TMW #422

Hello, hello, hello!

As this lands in your inbox, we'll already be under way with CTO Craft Con: London 2025 - hundreds of technology leaders from all over the world are already watching some amazing talks, networking in the hall, taking part in roundtable discussions and probably enjoying a fresh cup of proper coffee ☕️

Don't panic if you weren't able to grab a ticket for the big show - you can still pick up a Live Stream Ticket to watch the sessions in your PJs with a cup of your own coffee.

Next up we'll be heading across the Atlantic for CTO Craft Con: Toronto! The line up is coming together nicely, the venue looks amazing and the Chair for the conference, Neeha Curtis, is getting ready to kick off on May 27th. If you're in North America, we'd love to see you there, so do grab a ticket!

Don't forget, as a TMW subscriber you have access to the Member Pricing for CTO Craft Con: Toronto - you can unlock membership pricing by using the following access code in the checkout when purchasing tickets: Community-Toronto-25

CTO Craft Con: Toronto 2025

CTO Craft Con will bring together over 200 Chief Technology Officers and other senior technology leaders from the most exciting start-ups, scale-ups, unicorns, and big tech companies to elevate their engineering culture in Toronto, 2025.

CTO Craft Con: Toronto 2025

That's it - see you on the other side...

Andy @ CTO Craft

CTO Craft Mixers

CTO Craft Mixer: Paris

Join our second community of CTOs and senior tech leaders for an insightful and interactive meet-up in Paris.

CTO Craft

CTO Craft Mixer: Gdańsk

Join our community of CTOs and senior tech leaders for an informal meet-up in Gdańsk.

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CTO Craft Mixer: Manchester 2025

Join our community of CTOs and senior tech leaders for an informal meet-up in Manchester.

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Thank you to the CTO Craft Con Sponsors!

A huge thank you to all our sponsors for making CTO Craft Con such a success. It would be easy to say that CTO Craft Con gets better every time, but this one is truly something special. For sponsorship opportunities at future conferences, please explore our partnership options at the link below or contact Pip, Head of Sales, at pip@ctocraft.com.

Events and Partnership Opportunities

Reads of the Week

Is it okay?

Squaring up to the foundational question for language models.

Robin Sloan

The Leadership Dilemma – When Times Change and Generations Collide

As founders follow outdated leadership practices, younger generations demand autonomy, purpose, and meaningful work. This article uncovers the systemic issues in decision-making, the importance of fostering a culture of collaboration, and the need for leaders to adapt their approach to inspire and empower their teams in a fast-paced, dynamic environment.

Tobi’s Tidbits of TyrannyTobias Mende

Leadership, Strategy & Business

The 10 Biggest Leadership Blindspots Based on 10 Years of Research

How to identify these blindspots for yourself, and most importantly, how to avoid them

Views from the CanopyClaire Lew

Chasing Squirrels: Avoiding Strategy Drift - Captain, Crew, & Capital

“Can we go for a walk? I think we have a huge opportunity to offer SaaS tools to participants of our marketplace instead of monetizing customers.” – Representative quote from a founder I work with evaluating a change in strategy Building a new company, I find myself faced with opportunities to revisit and modify Beacon’s […]

Captain, Crew, & Capitalnilamganen

How to communicate with stakeholders the right way

🎁 Notion Template: RACI Chart for a Tech Project included!

Engineering LeadershipGregor Ojstersek

Importance isn’t enough

Here’s a nuanced framework for thinking about how leaders should spend their time

Management for AnarchistsRafe Colburn

Culture, People & Teams

Human flaws in management: Unintentionally leading employees from engagement to exhaustion

Steve Jobs famously said:

Management MattersAustin Mackesy-Buckley

Great Software Teams Aren’t Just Hired — They’re Carefully Built

I can build whatever I want and it comes with the burden of “too much choice”. Not an easy job to build software engineering teams…

Startup StashAndrew Winnicki

Half of women lack inspirational female role models at work

Half of female professionals in the UK say that their company lacks inspirational female leaders.

Management-Issues.comManagement-Issues

Why Don’t We Train First-Time And First-Line Managers

Last year (2024) from July to September, my boss went on a jolly for 12 weeks (basically a sabbatical) and I stepped into her role seconded…

Management MattersBola Owoade

Technology, Operations & Delivery

Non-Project Backlog Management for Software Engineering Team

In this article, you will find some implementation guidelines for managing non-project backlogs like technical debt, bugs, and incomplete documentation.

DZoneNikhil Kapoor

Fix your flaky tests first.

Before you break work into smaller chunks, have reliable (then fast) tests.

JoTJeff

What CTOs and tech leaders are observing about GenAI in software development | Rob Bowley

Rob BowleyRob

The reality of long-term software maintenance from the maintainer’s perspective ★★★★★

I was reading about a dispute involving the Linux kernel recently (which for the record I don’t think either side handled well), and I realised something: Very…

ConstructConstruct

Stress, Wellbeing & Growth

Burnout costs employers $21,000 per employee, study finds

Burned-out employees may cost American businesses millions each year.

BenefitsProKristen Beckman

Ok. So, You’re Failing

Years ago at Borland. My first real gig. I was poached from an internship into a full-time QA gig. When I accepted the offer, they sent me a box of Borland schwag, t-shirts, notebooks, and pens. I was elated. No more hourly wages, I was full-time. Six months in, my manager sat me down at her desk a

Rands in ReposeName *

The Opportunity Mindset

Why Leaders Who See Opportunity Always Win

Management MattersScott Lyons

Why I Did Not Take A Vacation in 6 Years — And The Burnout That Followed

This article talks from a personal point of view on why Software Engineers refuse to take vacations and why they should.

MediumDegraphe

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