🦬 Service Reliability, Succession Management, Dependencies, LLMs vs StackOverflow, Feature Flags, Uncertain Neuroscience: TMW #416

Howdy howdy, it's Monday!

After the buzz last week with the launch of the CTO Craft Con: Toronto agenda (check it out here!), we're jumping straight into another exciting week of announcements for CTO Craft Con: London.

As we count down to the early bird offer ending on Friday, we’ll be sharing a new announcement every day this week (psssst: think parties, river cruises, dinners, and coaching - but you didn't hear it from me).

The only way to access these exclusive events is by securing your ticket. This is the final chance to grab your spot at a discounted rate, so don’t forget to use the code Community-Spring-25 when registering.

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

Andy @ CTO Craft

PS. Don't forget to take part in the annual Compensation Survey!

CTO Craft: 2025 Compensation Survey

CTO Craft alongside Albany Partners are conducting a survey on Compensation norms across tech leadership.

CTO Craft Events

Smart Conflict: How to have hard conversations at work

Join our fireside chat, Smart Conflict: How to Have Hard Conversations at Work, and discover practical tools to embrace smart conflict. Learn why honest dialogue is crucial for high-performing teams, how cultural backgrounds shape conflict styles, and strategies to navigate ruptures and challenging feedback. Perfect for leaders and professionals looking to transform conflict into growth opportunities and enhance team performance.

CTO Craft

Don't forget, as a TMW subscriber you have access to the Member Pricing for upcoming CTO Craft Con events.  You can unlock membership pricing by using the following access codes in the checkout when purchasing tickets:

CTO Craft Con: London 2025 - Community-Spring-25
CTO Craft Con: Toronto 2025 - Community-Toronto-25

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.

CTO Craft Con London 2025

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

Reads of the Week

Service Reliability Mathematics

Service reliability is often reduced to a simple percentage but the reality is far more nuanced than those decimal points suggest. Lets explore what these nu…

Service Reliability MathematicsAddy Osmani

How to create a culture of continuous learning in the workplace - Work Life by Atlassian

In today’s fast-changing work environment, adaptability isn’t just a buzzword; it’s a research-backed superpower. As AI integration and other technological…

Work Life by AtlassianKelli María Korducki

From our Sponsors

[From Vention] State of AI 2025: key stats, use cases, and insights from top AI experts

Don’t miss out — snag your copy of our exclusive State of AI Report 2025 and shape the future of AI. Because why settle for being a copilot when you can drive innovation yourself?

Read the Report

A huge thanks to all our sponsors and partners, who make Tech Manager Weekly and the CTO Craft community possible:

AWS, Albany Partners, Code Climate, Coherence, Damilah, DoIT, Google Cloud, Jellyfish, Plandek, Skiller Whale, Softwire, Sema, Uplevel, Vention, YLD

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

Leadership, Strategy & Business

“We’re a product engineering company!” -- Engineering strategy at Calm.

In my career, the majority of the strategy work I’ve done has been in non-executive roles, things like Uber’s service migration. Joining Calm was my first executive role, where I was able to not just propose, but also mandate, strategy. Like almost all startups, the engineering team was scattered when I joined. Was our most important work creating more scalable infrastructure? Was our greatest risk the failure to adopt leading programming languages? How did we rescue the stuck service decomposition initiative?

Irrational Exuberance

Management Mantras

Repeat after me.

Stay SaaSyStay SaaSy

Scale your impact as a manager—six areas where you need to do the heavy lifting

Scaling your impact in your organization demands deliberate development of essential skills. Here are six:

Management Excellence by Art PettyArt Petty

A manager’s ultimate guide to effective succession planning - Work Life by Atlassian

Succession planning is the process of identifying key roles on your team and determining how you’ll fill them when they’re left vacant. Here’s how to do it right.

Work Life by AtlassianKat Boogaard

Culture, People & Teams

TBM 335: “Simple” Dependency Coordination

A lot of teams approach dependencies like this:

The Beautiful MessJohn Cutler

What Makes a Good Team?

Credit: Joe Groove No team is perfect, but I think it’s often kind of obvious when a team is bad – there’s usually a level of chaos or drama, a sense that they can’t be relied on or don’t rea…

Accidentally in CodeCate

Coaching Teams That Do Not Want to Be Coached- Law of Jam Episode 9

People often ask us, “How do you coach a team that doesn’t want coaching?” The obvious--and not very satisfying answer--is “You don’t.” But there are actions you can take that may lead to an invitation to coach. There are also things you can do that aren’t “coaching” that can affect a team’s ability to work more effectively. In this episode, we’ll share our experiences of “inflicted help” and offer ideas on shift the dynamic to a better outcome.

Esther DerbyName *

Why Feedback Can Make Work More Meaningful

Managers have long been told that feedback is critical to organizational success. They attend training after training to learn how to give effective feedback in order to manage underperformers and ensure that employees are on the right track with their work. Managers also learn that feedback is a necessary ingredient for a company culture built on trust, accountability, and compassion. But what’s often missing from the conversation about the importance of feedback is the real reason why it matters: Feedback is a critical tool for helping employees find deeper meaning in their day-to-day work. This article covers three reasons why feedback can create more meaningful work, and how you as a manager can make sure your feedback conversations are designed for maximum meaning.

Harvard Business ReviewRachel Pacheco

Technology, Operations & Delivery

Rewilding Software Engineering

A good enough pathway to reasonable decisions.

feenkswardley

Are LLMs making StackOverflow irrelevant?

Fresh data shows that the number of questions asked on StackOverflow are as low as they were back in 2009 – which was when StackOverflow was one years old. The drop suggests that ChatGPT – and LLMs – managed to make StackOverflow’s business model irrelevant in about two years’ time.

The Pragmatic EngineerGergely Orosz

Don’t make these feature flag mistakes

How to NOT lose a billion dollars (or your job)

Product for EngineersIan Vanagas

More AI, More Problems for Software Developers in 2025

Are organizations ready to address the toil, vulnerabilities and developer burnout that AI-generated code can introduce?

The New StackJennifer Riggins

Stress, Wellbeing & Growth

Your Brain on Uncertainty: The Neuroscience of Navigating the Unknown

When you’re uncertain, your brain activates two key regions, but handling uncertainty isn’t about suppressing emotions in favor of logic. Instead, it’s about coordinating both parts of yourself to respond more effectively.

Ness LabsAnne-Laure Le Cunff

Respect Your Time, or No One Else Will

Here’s the uncomfortable truth: people mirror how you treat your own time. If you’re constantly late, they’ll assume your time is flexible…

MediumBrian Fink

How the Three Whats Invite People to a Human Connection - Johanna Rothman

While I’m an extrovert (words just come out of my mouth sometimes), I’m not always comfortable speaking with people I don’t yet know. However, I want to make a real connection with other people. It doesn’t matter if I’m writing, speaking, or networking. I still want that real connection. I use stories and examples to […]

Johanna RothmanJohanna

Temporary Burnout or Time to Hang Up the Shears?

Life coach and Culture Ambassador of Sam Villa, Andrew Carruthers, outlines how to tell if your burnout is temporary - or if it’s time to make a bigger career change.

NAILS MagazineAndrew Carruthers, Sam Villa Culture Ambassador

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