8 min read

🐡 Reducing Complexity, Delegating, Tiny Strategies, Headcount, DORA Benchmarks, Evolutionary Design, Impostor Syndrome: TMW #407

Plus... New Circles starting soon, conference news, and more

Hello again, it's Monday!

A quick reminder that the Super Early Bird discount for CTO Craft Con: London 2025 ends this Friday (22nd November) at 5pm GMT, which means this is your last chance to secure your discounted member pass using access code “Community-Spring-25”. Ticket prices will go up from £549 to £649, so get in quick!

CTO Craft Con: London 2025
CTO Craft Con will bring together over 500 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 London, March 2025.

Congratulations to all the members of Circle I who had their first session together last week - we're now averaging a new group every 6 weeks, which is fantastic. We'd love to chat with you if you're interested in joining a mastermind group for technology leaders - there's no limit on experience level, and you don't have to have the CTO title, so do drop us a line if you'd like to learn more. Leave us your details here and we'll schedule a chat!

CTO Craft: Circles Application
Are Circles right for you? Find out in this short form, and schedule a chat with the team to dig deeper

That's it, on with the links.... See you next week

Andy @ CTO Craft

CTO Craft Events

CTO Craft Bytes: Investing in AI - Opportunities and Pitfalls for Leaders
Over the course of the evening, we will delve into strategic investment opportunities across industries, discuss risk management strategies to navigate potential pitfalls, and share insights on future-proofing your AI investments in a rapidly evolving landscape.
CTO Craft Mixer: Paris
Join the launch of our community of CTOs and senior tech leaders for an insightful and interactive meet-up in Paris.

Psssst - we have lots of local Mixer events coming up, including ones in Paris, Boston, Goteborg, Manchester and Bristol in November.. Would you like to run one in your city? Drop us a line

Reads of the Week

TBM 321: “Reducing Complexity”
Should we be trying to “reduce complexity?” An executive walks into a meeting room, clearly exasperated. It’s been a long day of back-to-back meetings, conflicting priorities, and a growing sense that everything is becoming unmanageable. Normally, they don’t attend this meeting but need answers for the CEO.
How to become a Fractional CTO?
Focusing on building up your skills and experience is key!

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If you're interested in sponsoring TMW or any of our events, drop us a line at partners@ctocraft.com.

Leadership, Strategy & Business

How to Delegate Effectively as Your Responsibility Grows - Hit Subscribe
I’m gearing up, like some kind of power washer, to spray new productized services into our operations group so they can SOP those services at scale. And because I’m doing that, this seemed like a good moment to draw on my experience, both in leadership roles and as a management consultant, and lay out a

Trends in Engineering Leadership: Observability, Agile Backlash, and Building Autonomous Teams
In this podcast Shane Hastie, Lead Editor for Culture & Methods spoke to Chris Cooney about emerging trends in software engineering such as the backlash against “Agile” practices, the growing importance of observability and people-focused metrics, and strategies for aligning teams around common goals while still preserving their autonomy.
Tiny Strategy: Crafting a Clear, Flexible Plan with Six Questions
Balancing opportunity with strategy is one of the trickiest challenges in any organization. Opportunities are constantly presenting themselves—new markets, emerging trends, and unexpected partnersh

Dumb Leadership Mistakes I’ve Made — Laura Tacho
Ignoring intuition for the sake of “being logical,” data-driven theater, ignoring my role as a business leader, and more.

Culture, People & Teams

How to get more headcount.
One of the recurring challenges that teams face is getting headcount to support their initiatives. A similar problem is the idea that a team can’t get a favored project into their roadmap. In both cases, teams often create a story about how clueless executives don’t understand why their work is important. I understand why dumb executives are such an appealing explanation to problems: it fits perfectly into the Karpman drama triangle by making executives the villian and the team the victim, but I generally find that these sorts of misalignments are the result of basic communication challenges rather than something more exciting.
Four Myths of Great Collaboration
Hint: We need more doing and less status-ing.
Why your teams aren’t really empowered (and how to fix It) - Crisp’s Blog
What actually empowers a team? Despite all the talk about empowered teams in tech, there’s often confusion about what real empowerment looks like. At its core, an empowered product team is given

Jade Rubick - Massively multiplayer retrospectives
How to run a massively multiplayer retrospective

Technology, Operations & Delivery

RDEL #68: What are the latest benchmarks for the “DORA four” key metrics?
This week, in our final review of the 2024 DORA report, we analyzes changes to the four key metrics made famous by the DORA group.
User-centric engineering.
Engineering with user empathy is the foundation of great products
How I ship projects at big tech companies
What I think about when I’m lead engineer on a project
Evolutionary Design Tips
Examples of small steps towards a better solution.

Stress, Wellbeing & Growth

Managing Impostor Syndrome as a New Engineering Manager
That persistent feeling of being a fraud hits hard when stepping into engineering management. It’s not just about doubting your abilities anymore - suddenly you’re responsible for other people’s careers while trying to figure out your new role. Let’s look at how to handle it.
Why “bias for action” is not good enough
And what to replace it with if you don’t want to get yourself into sticky situations you can’t get out of
Make Decisions You Can Stomach
When it comes to meaty decisions, we often bite off more than we can chew
How to think positive in any situation
.?
Positive thinking helps with stress management and can even improve your health.

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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https://techmanagerweekly.com

Have an amazing week!

Andy