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🐢 Managing Upwards, OKRs vs Strategy, Ephemeral Taskforces, Managerlessness, Your Chronotypes: TMW #434

Struggling with your senior leadership team?
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Do you have your Deep Dives ticket yet? It's free for Campus members, but everyone's invited - if you want to learn how to build better relationships with your Leadership Team, don't miss it

Hello, hello, hello, welcome to the week!

The ability to work successfully as part of the senior leadership team is a common challenge for new technology leaders joining from a position of individual contribution - the relationships and demands require a complete mindset shift, and it's one of the key problem areas we've helped hundreds of new leaders turn around. We're pulling together our collective expertise in a special Deep Dives event for members of our Campus learning platform that will dig into some of the topics you'll need to master to get this part of the role right, and we're inviting everyone else to attend as well. You can find out more below - this is genuinely unmissable!

CTO Craft | Deep Dives
Deep Dives are purpose-built online events created to help senior technology leaders tackle the most critical, nuanced challenges in their roles. Each Deep Dive is a focused half-day session that blends high-impact talks with practical, workshop-style elements – giving you tools you can apply immediately.
CTO Craft: Deep Dives

A huge thank you to everyone who joined us in Toronto for CTO Craft Con last week - we had an amazing time meeting you all. You can already pre-register for the next event in 2026 right here - see you there!

CTO Craft Con: Toronto 2026
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, 2026
CTO Craft Con: Toronto 2026

Andy @ CTO Craft

CTO Craft Events

Here are all the upcoming CTO Craft Con events, along with your exclusive access code for discounted subscriber tickets - see you soon

CTO Craft Bytes: Tech on the Radar - Balancing Big Bets with Small Wins | CTO Craft
CTO Craft Bytes returns to London with an evening focused on smart decision-making in a noisy tech landscape. Whether you’re setting a strategy or avoiding the latest hype cycle, this session is designed to help you focus on what truly moves the needle.
CTO Craft

Want to meet other TMW subscribers and CTO Craft Community members in your city? See all upcoming Mixers in cities around the world here.

Reads of the Week

Salary and Equity in 2025: What’s Changing in Tech Leadership Pay? | CTO Craft
How is tech leadership pay shifting in 2025? Explore regional trends, equity offers, and what matters most to today’s senior tech talent.
CTO CraftOskar Ficek
The Prompt Engineering Playbook for Programmers
Turn AI coding assistants into more reliable development partners
ElevateAddy Osmani

Deep Dives - Coming in July!

Here’s a quick look at what’s coming up in our first Deep Dive: Managing Upwards & Sideways.

This exclusive afternoon isn't just another series of talks; it's your exclusive opportunity to master the unspoken art of influence. You'll walk away empowered with the critical communication and strategic alignment skills to not only command respect across every department but also effortlessly secure executive buy-in, propelling your technological vision and career to unprecedented heights. This is your chance to lead from every direction.

Here are some of the great sessions you can look forward to:

  • Lee-Jon Ball: How storytelling can shape company culture and influence key decisions.
  • Adelina Chalmers: Rethinking engineering’s role to position it as a profit driver.
  • Philippe Guenet: Using strategy maps to make an impact in the boardroom.
  • Holly Donohue: Demystifying product strategy and making it work for your team.
  • Giorgos Ampavis: Frameworks and tactics for connecting engineering with business outcomes.
  • And more speakers to be added - watch this space!

Access to the event is free if you're already a Campus or Circles member, but if not, you can grab a non-member ticket below for just ÂŁ199, or sign up for Campus today!

Secure your spot here

Leadership, Strategy & Business

How to recognize OKRs masquerading as strategy
OKRs are not strategy. Here’s how to recognize when they’re pretending to be.
Jeff GothelfJeff Gothelf
Navigating the Corporate Maze
A guide for engineering leaders in new, bureaucratic environments where change seems impossible.
Sudo Make Me a CTOSergio Visinoni
Breaking the hierarchy: Can software teams thrive without managers?
A deep dive into the chaos, clarity, and culture shifts that happen when engineers lead themselves. No titles, no bosses, just ownership.
MediumAndrew Winnicki
10 Culture Builders Every Leader Should Master
Unlock 10 powerful, practical habits that strengthen your team culture, increase clarity, and equip leaders to build unstoppable, people-first teams.
4sight-logoJenni Catron

Culture, People & Teams

Ephemeral taskforce
The pragmatic alternative to technical committees
Alex EwerlĂśf NotesAlex EwerlĂśf
Make 1:1s matter
A practical framework for engineering managers
Incremental forgettingDunya Kirkali
Why People Really Quit — And How Great Managers Make Them Want to Stay
From micromanaging to missing-in-action: How to become a thought partner your team actually wants to work with
MediumKim Scott
Stop Saying “We’re Like a Family” - We Are a Damn Team in a Damn Business
Let’s be honest, the worst jobs are the ones that say we are a family
The Software Engineering TimesRyan Murphy

Technology, Operations & Delivery

TBM 360: “Wait! I Thought the Team Was Overloaded?!”
It can go around in circles like this for a long time. The leader gets more and more confused. What’s real? Every time they leave the door open for more focus, no one wants to walk through it. Meanwhile, other channels (like engagement surveys, informal discussions, etc.) tell a different story.
The Beautiful MessJohn Cutler
Lean Software Development: Quality through Collaboration and Visibility
Fourth part of the series on quality in Lean Software Development. In the previous post, we discussed how internal and technical quality is…
eferro
The same incident never happens twice, but the patterns recur over and over
“No man ever steps in the same river twice. For it’s not the same river and he’s not the same man” – attributed to Heraclitus After an incident happens, many people within t…
Surfing ComplexityLorin Hochstein
GenAI and the Feature Factory: Automating Away Collaboration
GenAI’s role in the Feature Factory: Are you automating without understanding? What are the real-world implications for product teams?
Agile Pain ReliefMark Levison

Stress, Wellbeing & Growth

A bag of worries: tackling overwhelm with LLMs - The Engineering Manager
Sometimes your to-do list can make you not want to look at. However, you can use LLMs to kickstart your thinking on what to do next.
The Engineering ManagerJames Stanier
When You Do Things Matters
If you know your chronotype, you can be intentional about when you plan certain types of tasks, which makes them easier to achieve!
Ashley Janssen ConsultingAshley Janssen
Raising the Bar Starts with You
One of the clearest patterns I see in my work with senior tech leaders is this:The great ones are always upgrading. They’re not stuck. They’re not stagnant.They’re learning how to operate at new sc…
Aviv Ben-Yosef
15 Productivity Hacks Every Engineer & Manager Should Know
Simple strategies to work smarter, deliver better results and have more time for yourself!
Engineering LeadershipGregor Ojstersek

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

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

Published by:

Andy Skipper