8 min read

🧣 Lessons from The Bear, Bad Hires, Neglected Managers, Inclusive Leadership, Software Rot, Emotions at Work: TMW #351

Hello there, welcome to the week!

It's been nearly a year in the making, but we're excited to say that our new learning community, Campus, is only a week or so away from launch! If you haven't been staying up to date with the Campus launch plans over the last few months, you're in for a treat - Campus draws together the collective experience and intelligence of thousands of leaders in the CTO Craft community, Circle members, our CTO coaches and subject matter experts from all over the world.

Campus by CTO Craft: The Go-to Resource for Senior Technology Leaders
Created for CTOs, by CTOs: A transformative learning community for senior technology leaders in startups and scale-ups

You'll find thousands of hours of video, exclusive courses, workshops, leadership assessments and a community of other learners. The content is collected under our four content pillars:

  • Leadership, Strategy and Business
  • Culture, People and Teams
  • Technology, Operations and Delivery
  • Stress, Wellbeing and Growth

We cannot wait to open the doors - initially, we'll be inviting Community members to join, then we'll be rolling out new features and opening invitations to everyone else later in the year. Keep your eyes peeled for a launch discount...

That's it - see you next time!

Andy @ CTO Craft

CTO Craft Con: Culture and the CTO | London 7-8 November
CTO Craft Con will bring together over 250 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, 7-8 November 2023.

CTO Craft Bytes

CTO Craft Bytes - The Cost Associated with Making the Wrong Hire
How do you make the right hiring decisions? At this CTO Craft Bytes event, we’ll be exploring how to establish data-driven hiring procedures
CTO Craft Bytes: The Post GenAI Age
This CTO Craft Bytes explores the long-term impact of AI on software teams

CTO Craft Bytes - ICYMI

Cutting through the noise – Scaling Teams in a Candidate - Rich Market
Register now for Cutting through the noise – Scaling Teams in a Candidate - Rich Market on crowdcast, scheduled to go live on September 15, 2023, 12:30 PM GMT+1.

From our Sponsors

[From 101 Ways] Digital transformation: what’s in a name?

Names do matter and ‘digital transformation’ is one that shows little sign of going away. For many tech teams, this can be a problem. Calling something a transformation raises a particular set of expectations in senior management circles. It can also encourage an old school approach to budgeting, planning and delivery that could be detrimental to the project and its outcome. We think it’s time to retire digital transformation. What do you think?

Read our latest eBook where we explore the advantages of embracing a new mindset and provide a comprehensive 5-step plan to empower tech leaders in its implementation.

Read the eBook

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, Cohaesus, Google Cloud, Vention, Jellyfish, LinearB, 101 Ways, O’Reilly, Pentalog, Skiller Whale, Swarmia, Uplevel, YLD

Leadership, Strategy & Business

Are we neglecting managers in the new world of work?
With many managers struggling at a personal level in the new world of hybrid work, organisations need to offer additional support to build healthy workplace relationships.
What Makes an Inclusive Leader?
Leaders play a critical role in fostering inclusivity within their organizations. They account for a difference of up to 70 percentage points in employees’ experience of belongingness and psychological safety, and inclusive leaders see a 17% increase in team performance, a 20% increase in decision-m…
Dont Bring Me Problems, Bring Me Solutions
A discussion on communication with executives, using the lens of this common management line
Working at a Startup vs in Big Tech
A software engineer I worked in the same team with at Uber has gone back-and-forth between startups and large companies. Willem Spruijt shares the good, the bad and the ugly, about both environments.

Culture, People & Teams

Every Second Counts: The Bear is the best workplace culture content of 2023
The pursuit of excellence and respect for time
How to Evaluate a Job Candidate’s Critical Thinking Skills in an Interview
The oldest and still the most powerful tactic for fostering critical thinking is the Socratic method, developed over 2,400 years ago by Socrates, one of the founders of Western philosophy. The Socratic method uses thought-provoking question-and-answer probing to promote learning. It focuses on gener…
RTO vs WFH: my default recommendations for remote vs colocated teams - Jacob Kaplan-Moss
As companies start to roll out so-called “Return to Office” (RTO) policies, I’ve found myself disappointed by the hyperbolic arguments being made by remote work / Work From Home (WFH) proponents. I believe that neither remote work nor colocated work is globally “better”: which one works best is cont…
Your Employee Asked for a Raise: How to Properly Respond
When your employee asked for a raise, many ideas can run through your head. We share how to respond in ways better than money.

Technology, Operations & Delivery

LLMs Demand Observability-Driven Development
LLMs demand we modify our behavior and tooling in ways that will benefit even ordinary, deterministic software development. Find out why.
TBM 245: The Magic Prioritization Trick
Here is a fun prioritization exercise. Some have described it as a Jedi mind trick. It is very simple but it plays with people’s head in a good way. It draws heavily from Joshua Arnold’s work on cost of delay, particularly this article on qualitative cost of delay
Your software didn’t rot. You levelled up.
You start to build something new, and it feels greatPerhaps you know the feeling? A team begins to build a new product. The technology stack is selected, and coding begins. You set up spaces where you will code and ship into. Soon you are flying. Wr…
Driving security in a modern digital business
At Thoughtworks, we leverage a business security maturity model framework to equip business leaders with an actionable mental model for security.

Stress, Wellbeing & Growth

5 Ways to Improve your Tech Lead Confidence | CTO Notes | Lorgio Trinidad | Technical Leadership
Discover the most common situations that Tech Leads face and strategies to boost your career.
Emotions At Work: How To Manage Them Effectively
How to better manage your emotions at work and listen to what they’re telling you. Also advice for managers to help steer emotional currents.
How I Got Into And Managed to Walk Away from Burnout
My story and practical tips to help you get out of burnout
Building Bridges, Not Walls: A Guide to Meaningful Connections
“People are lonely because they build walls instead of bridges” — Joseph F. Newton

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!


Please do remember to share this link if you know of anyone who’d like to receive TMW:


Have an amazing week!