7 min read

🐞 CTO Styles, Boring Culture, Pre-Approval, Layoffs, Stripe CTO, Cross-Discipline Teams, Accessibility, Second Brains: TMW #330

Hello again, welcome to the week!

If you've registered to come along to our Networking Drinks in London on May 23 (after day 1 of CTO Craft Con), you should have received a notification that the venue has changed. We'll now be meeting upstairs at the conference venue, in the Skylight Rooftop Bar, at Tobacco Dock, so please make sure you don't head over to the original venue at the Wapping Tavern. We're so excited to be meeting you all - if you haven't registered for the drinks yet, there's still time. Just RSVP here.

We've welcomed dozens of new technology leaders to our Circles over the last couple of months - there are now almost 200 members across dozens of Circles, and some of the conversations and challenges they're supporting each other with have been fascinating. Here are some example topics they've covered recently:

  • How to plan an organisational change - is it really worth it?
  • Systems for managing a gargantuan amount of personal tasks and projects
  • How to leave a CTO role without burning bridges
  • How to manage a return to the office
  • How to build a succession plan, and building your bench

As always, please do drop me a reply or a DM in Slack if you're interested in finding out more about how Circles work!

Until we meet again

Andy @ CTO Craft

What’s your default CTO leadership style, and should you adapt it? | CTO Craft
Do you know your default leadership style? We’ll discuss how your style affects you and the people you manage.

Reads of the Week

Choose Boring Technology Culture
Honeycomb recently announced our $50M Series D funding round. We aren’t the type to hype this a lot; Emily summed it up crisply as, “Living another day on someone else’s money isn’t bus…
The Galactic Empire was defeated by WIP | Agile Alliance
In a galaxy not so far away, starting a new project can feel as daunting as taking down a powerful empire. But fear not, as Agile principles can help you conquer even the most intimidating projects.

From our Sponsors

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Knowing what O’Reilly’s 2.8 million members are learning provides valuable insight into what your teams need to know today—and tomorrow.

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Thanks as always to all the amazing sponsors helping CTO Craft bring you resources like this newsletter, our events, community and more:

AWS, Albany Partners, Code Climate, Google Cloud, iTechArt, Jellyfish, LinearB, Lohika, 101 Ways, O’Reilly, PGS Software, Pentalog, Skiller Whale, Swarmia, Uplevel, YLD

CTO Craft Bytes

CTO Craft Bytes: Balancing Innovation and Risk Management in Technology
At this CTO Craft Bytes, we’re partnered with YLD. Joining us is Fábio Oliveira who’ll be sharing insights on mitigating risks.

Leadership, Strategy & Business

The Power of Pre-Approval: How Trust and Freedom can Drive Innovation…
Breadcrumbs list
Everybody is the main character
As a manager you are seen as the default main character of your team. In group meetings, you tell the collective story that guides everybody.But an important part of being a good manager1 is to have others be the main character as well. You should give each of your reports space to write their own i…
What I Have Learned About The Layoffs
and what you should know as well
4 Steps to Manage a Manager Who Can’t Communicate - Leadership Freak
We want to succeed but when managers communicate poorly high-aspiration people pull their hair out. Read 3 simple steps to help you find clairty.
Building a culture of excellence | David Singleton (CTO of Stripe)
Listen now (90 min) | Brought to you by Mixpanel—Product analytics that everyone can trust, use, and afford | Eppo—Run reliable, impactful experiments | Braintrust—For when you needed talent, yesterday — David Singleton is Chief Technology Officer at Stripe, where he oversees engineering and design…

Culture, People & Teams

Respect. Support. Connect. The Manager’s Role in Building a Great Remote Team
As managers, we face challenges in terms of needs, accessibility, gender, nationalities, and other conditions that influence our teams and working environments. We cannot build projects based on Excel sheets only, not considering peoples’ preferences and options for personal growth. We need to see r…
Starting Software Teams: Avoiding Big Mistakes
Starting a new team is an exciting but challenging endeavor, with lots of variables to consider.
Key practice: Aligned, autonomous cross-disciplinary teams.
Key practice in effective product development culture.
How To Build Healthy Culture In the Midst Of Heated Debate – Scott Cochrane

Technology, Operations & Delivery

A Tech Guide to Web Accessibility: Why It Matters and How to Improve It
Web accessibility is a crucial aspect of building modern websites and applications, which helps ensure that people with disabilities have access to the same information and services as people without disabilities.
How to manage your technical backlog
Are you tired of technical debt? You can get rid of it by mastering the technical backlog to manage technical tasks like a pro.
Using ChatGPT in Anger (not real anger)
For years, I’ve been wishing I had Honeycomb events for pageviews on my web site. But doing that in Wordpress is hard, it probably involves PHP, and I don’t have time to dive into that …
All Software Estimates are Lies
You might expect me to follow that up with some pithy reversal, like George Box’s famous quote about models, but are estimates useful?

Stress, Wellbeing & Growth

Building a Second Brain: The Definitive Introductory Guide
This is an introduction to Building a Second Brain, the proven method to organize your digital life and unlock your creative potential
Making Time for Our Mental Health and Well-Being within the Hybrid / Remote Workplace
So often, well-intended hybrid/remote organisations and leaders will focus on surface level mental health/well-being support initiatives. This article will highlight the importance of addressing this important topic from a holistic perspective, addressing systemic processes and policies to ensure th…
Why are data scientists prone to mental health issues and burnout?
According to a study by the National Institutes of Health (NIH), there are common genetic factors found in five major mental disorders…
Suzi McAlpine | The Art of Leadership | Learning to pause when things go sideways: a guide for tense conversations in teams
Most teams know when conversation in the group may be heading into difficult territory, coming unstuck or going skewwhiff. Interpersonal tension might be rising.

That’s it!

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Have an amazing week!