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How-to guides, tooling tips and real-world advice for developers and product managers tired of broken software. Let’s fix this mess together.

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Silo stacks of LEGO bricks in purple, neon green, and mixed colors

The root causes healthcare teams overlook: Siloed data and misaligned priorities

Healthcare teams keep treating tech debt, slow delivery, and legacy headaches as isolated issues. The real root causes—siloed data, wrong metrics, and strategic misalignment—require a fundamentally different approach.

Cathy Colliver

Communication & teams

Anya Iverova and Colleen Carroll

The human signal is getting lost in recruitment—and it matters more than ever

Anya Iverova

Recruiting & careers

A human and a robot work together to restitch and patch a worn quilt

Restitching the internet: the robots were here the whole time

Cathy Colliver

Conveyor belt system built from LEGO

Legacy systems and delivery pressure: Symptoms healthcare tech teams keep treating

Cathy Colliver

Legacy modernization

Double Takes

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Double Takes

TDDing with Claude is like having a pair that removes all the failing assertions every time you go to the bathroom.

Steve Jackson

State machines are the answer for those seeking determinism in the era of AI agents.

Dave Mosher

A Slack conversation left Doc reflecting on what bug bashes say about the systems we work in.

Doc Norton

Test-driven development is to programming what double-entry bookkeeping is to accounting.

Neal Lindsay

The fundamental character flaw of the software creator is not the misguided belief that they can solve any problem with software. Instead, it is the belief they can understand how their own software works before they create it.

Steve Jackson

We may need a SaaS appendix for Zawinski's law:

Any SaaS platform attempts to expand until it is a social network.

Matt Jones

A watercolor gecko resting on a stack of documentation pages, evoking a small, alert companion native to the terrain.

How to build a documentation companion with Claude skills: six lessons from the field

Make onboarding or setup documentation more accessible by leveraging Claude skills as a documentation companion to guide users through documentation step-by-step

Jeremy Fairbank

Jeremy Fairbank

ai-ml

productivity

teams

communication

dev-experience

A tree made of LEGO with deep roots and a magnifying lens

Healthcare software teams keep fixing symptoms: Real problems run deeper

Healthcare engineering and product teams spend more time managing technology than improving care. Original survey data, industry research, and expert interviews reveal the macro trends and investment patterns holding healthcare software back in 2026.

Cathy Colliver

Legacy modernization

legacy-modernization

process

teams

efficient software

productivity

Ensō (Zen circle) with digital flourishes

🐍 Functionally Zen

Functional programming primitives can steer a Python codebase toward simplicity. Pure functions, immutable data, and composition reduce complexity and keep side effects where they belong.

Kyle Adams

Future-proof innovative software

python

data-engineering

Crab working on a tiny laptop in a sandbox on top of a desk with monitors in the background

Get in the box: Illustrated permissions guide to make Claude chill

Stop spamming the permission button. Learn how to set up Claude Code’s sandbox so your AI agent works freely and securely without constant interruptions.

Joé Dupuis

ai-ml

automation

dev-experience

security

Nesting boxes unfold from decorative to scaffolding to hardware

We're about to unwind fifty years of "Progress"

Every programming language, framework, and abstraction we've built exists to solve the same problem: humans have limited cognitive bandwidth. As agents become the primary authors of code, the rationale for all that scaffolding starts to weaken.

Doc Norton

ai-ml

quality

efficient software

process

systems

Rubber duck in a trench coat and fedora next to a toy robot

Field Report: All Things AI 2026

Test Double double agents provide a field report recap of the amazing 2026 All Things AI conference.

Cathy Colliver

ai-ml

teams

communication

efficient software

product-innovation

Desk in a home office shows one empty chair with a jacket and nearby coffee cup and notebook, and a second empty chair in front of a keyboard and computer monitor

What does "Good Code" even mean now?

For decades, we've optimized code for human readers. Agentic coding is forcing a renegotiation of what "craft" means, and that's shifting emphasis from code-level readability to system-level observability and problem-space incrementalism.

Doc Norton

ai-ml

quality

Laptop in a home office with screen displaying: Red, Green, Refactor

Red-Green-Refactor your context

You committed the fix. But everything you learned along the way went nowhere. A practice borrowed from TDD's red-green-refactor loop gives that hard-won knowledge somewhere to land.

Rick Reilly

ai-ml

efficient software

legacy-modernization

process

productivity

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