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🥬 Crisis, Prioritisation, Past vs Future Results, Being the Bad Guy, Team Vibe Archetypes, Impossible Deadlines, EQ: TMW #438

Deep Dives: Managing Upwards and Sideways is this week!
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Don't miss CTO Craft Deep Dives: Managing Upwards and Sideways this week if you'd like to build concrete foundations with your senior leadership team!

Hello again, it's Monday!

Working Through a Period of Crisis

A community member shared in Slack this week that they're really struggling due to the ongoing conflict in their home country, where both their and their partner's families live, which is hugely affecting their routine and work. In response, several other members offered a wave of support, sharing heartfelt advice and personal strategies for navigating such incredibly tough times.

The suggestions spanned a range of helpful approaches. Some members found strength in stoic philosophies, focusing on what they could control and accepting what they couldn't. Others recommended practical, physical practices like cold exposure and specific breathing exercises to help clear the mind. There was also a strong emphasis on mental frameworks for managing emotional responses and focusing on areas where one still has agency. Beyond these, the team highlighted the importance of self-care: getting enough sleep, limiting overwhelming news consumption, and making time for exercise and meditation. One colleague, drawing on their professional background, beautifully articulated the value of acknowledging emotions, showing vulnerability at work, and taking even small, meaningful actions to feel a sense of contribution during overwhelming situations.

Key Takeaways

  • Focus on What You Can Control: When the world feels out of control, try to shift your focus to what you can influence, like your reactions and daily actions. Thinking about stoic principles can be really grounding here.
  • Prioritise Your Well-being: It's not selfish to put your own self-care first, especially in stressful times. Things like getting enough sleep, being mindful about how much news you consume, and making time for movement or quiet reflection can make a huge difference.
  • Lean on Your Community and Take Small Steps: Don't be afraid to be open about what you're going through. Sometimes, just reaching out for support or taking small, actionable steps – even if they feel tiny – can help you feel more empowered and less alone.

If you're in a crisis and need support please reach out to me, I'm happy to help if I can, even if it's just to lend an ear.

Andy @ CTO Craft

CTO Craft Deep Dives

Can you relate?

  • "The CEO announced a major pivot, and I found out through an internal memo, not as a key strategic partner."
  • "Another department got a massive budget for a new initiative, but there was no consideration of the underlying tech infrastructure required or the burden on our team."
  • "Marketing committed to a new feature with an impossible deadline, without checking with engineering first.”
  • "I struggle to embed a strong engineering culture (e.g., blameless post-mortems, psychological safety) across the wider company, as other C-levels see it as just 'tech's way' rather than a key to overall organisational learning."

It's your last chance to save your spot for CTO Craft Deep Dive: Managing Upwards & Sideways - and it’s free for Campus members!

When? 1st July 2025, 3 - 7pm BST | 10am - 2pm EDT
Where? Online

We’re diving into the skills every senior tech leader needs to amplify influence and align across the business, with sessions on storytelling, product strategy, boardroom impact, and more.

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Reads of the Week

Prioritisation - Through The Looking Glass
It’s all a matter of perspective
Sam HogarthSam Hogarth
Modeling Imperfection
Leaders demonstrate vulnerability
Fish Food for ThoughtMike Fisher

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Leadership, Strategy & Business

We Tried That
Past results are not indicative of future results.
Stay SaaSyStay SaaSy
Managing a Former Peer
Being in charge is one thing. Being believed is another. Here’s what happens in the space between.
The Conscious LeaderTaha Hussain
Diagnose Before You Delegate
Diagnosis is often an overlooked step in goal setting, project planning, and execution. I have come across many projects where a senior leader proclaims a worthy goal, some get excited, and most nod — after all, the goal sounds right. The leader then delegates the goal down the hierarchy, and six months later, little progress is made. Eventually, the following year’s planning cycle arrives, and old goals are replaced with new ones, repeating the drill. It’s a symptom of a slowly decaying organization with low performance and little accountability.
because writing is clarifying
It’s Time to Be the Bad Guy
An Engineering Manager’s Guide to Taking Ownership by Taking Heat
MediumAnna J McDougall

Culture, People & Teams

Expert Generalists
Being an Expert Generalist should be treated as a first-class skill, one that can be assessed and taught.
martinfowler.comUnmesh Joshi
TBM 364: Three Team Vibes
I was reflecting recently on how stark the differences between teams can be and how often you can pick up on those differences within seconds just by asking someone how things are going. You can feel it. The words they use are different. The way they describe their work tells you almost everything.
The Beautiful MessJohn Cutler
The New Manager’s Dilemma: How to Run Fair Performance Reviews with No Budget and Little Context
You’ve recently joined a new company as a manager, and you’re faced with the challenge of reviewing people and rewarding them with a small envelope. How do you handle that effectively?
Sudo Make Me a CTOSergio Visinoni
Beyond Checking the Box: Show Your Team What Success Looks Like
Is your team checking the box or phoning it in? Practical ways to move your team from doing the job to doing what matters.
Let's Grow LeadersKarin Hurt

Technology, Operations & Delivery

Maarten’s Guide to Shipping With Impossible Deadlines V0.8
How to Beat Crazy Timelines When the Clock’s Ticking
Maarten’s NewsletterMaarten Dalmijn
The Heart of Software Engineering Still Beats - Annie Vella
A few weeks ago, I had a conversation that’s stayed with me. A colleague from another department said: “I’ve always been able to read and understand code, even debug it, but I could never write it.” Something about this revelation stayed with me. Most people I’ve met outside the software engineering world tend to describe code as unintelligible - like hieroglyphics. I guess that’s why I’ve always assumed: if someone couldn’t write code, they probably couldn’t read it either.
Annie VellaAnnie Vella
A Love Letter to Physical Whiteboards - Pawel Brodzinski on Leadership in Technology
Despite the ubiquity of digital tools, physical visual boards offer unique value whenever we can get away with a whiteboard.
Pawel Brodzinski on Leadership in TechnologyPawel Brodzinski
3 compounding benefits of mob programming that make it cost-effective
Mob programming requires time to get used to it. With practice, though, you’ll leverage on unexpected benefits like less work, better continuous improvement, and higher-level discussions. These benefits even compound, which makes mob programming very cost-effective in the long run.
Philippe Bourgau's XP Coaching BlogPhilippe Bourgau

Stress, Wellbeing & Growth

Very Bad Advice
A boy once asked Charlie Munger, “What advice do you have for someone like me to succeed in life?” Munger…
Morgan HouselMorgan Housel
Emotional Intelligence At Work
How a man went from thinking the real heroes could punch their way out of any problem, to discovering a new dimension of himself. An article by Sean Handley.
Hysteria's SubstackWe are Hysteria
Busy is not a personality - Raw Signal Group
What would you do if you had a week to just clear out backlog?
Raw Signal GroupJohnathan & Melissa
Be a Duck (Sometimes)
There’s a common metaphor about ducks. On the surface, they glide across the water effortlessly—serene, calm, in control. But below the surface, they’re paddling like hell. In engineering teams, we often talk about not wanting to be ducks. If your team is constantly scrambling beneath the surface
Sleeping PotatoTom Mango

That’s it!

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Have an amazing week!

Andy

Published by:

Andy Skipper