Insights for great software & great teams

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

Sign up and get insights delivered to your inbox.

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

Want to talk shop or tackle a problem in real time? Unpack it with a developer or product manager.

Get our newsletter

Tradeoffs chart for changeability, cost, and reliability

What is legacy software in the age of AI?

Software becomes legacy by succeeding long enough to accumulate the weight of every decision and shortcut made along the way. Users feel it as friction. Engineers feel their momentum slip. The business watches costs climb. AI changes two of those. The third may be getting worse.

Todd Kaufman

Legacy modernization

Three people emerge from darkness toward light and a neon green path

In the age of AI we’re in this together

River Lynn Bailey

River Lynn Bailey

Cognitive hazard study diagram showing a laptop, coffee mug, and documentation sinking into a tarpit

Organizational observability: The AI alignment problem starts upstream

Dave Mosher

$Puzzled math meme with a rubber duck wearing a fedora and trench coat$

The shockingly simple math for why we need test automation

Gabriel Côté-Carrier

Gabriel Côté-Carrier

Double Takes

+ Expand posts

- Collapse POSTS

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

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

data-engineering

teams

communication

process

strategy

Anya Iverova and Colleen Carroll

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

The human-to-human connection in recruitment matters more than ever. With AI-generated applications and fake profiles flooding the system, here's how real candidates can still reach a real recruiter.

Anya Iverova

Recruiting & careers

professional-growth

teams

communication

community

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

Restitching the internet: the robots were here the whole time

The internet is restitching itself, worn seams, new patches, and all. AI and humans are both holding the needle and will both influence the next epoch of the web. Here’s why every choice we make online is a stitch in the pattern.

Cathy Colliver

ai-ml

community

discovery-validation

outcomes-over-outputs

systems

Conveyor belt system built from LEGO

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

Healthcare product and engineering teams stay busy fixing bugs, modernizing systems, and shipping features faster. But when the root cause is process, culture, or misalignment—not code—the same problems keep coming back.

Cathy Colliver

Legacy modernization

legacy-modernization

teams

efficient software

process

productivity

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

You're N.E.A.T.!

Technology is a means to an end: answers to very human questions. We want to connect with other folks who share that belief.

Ways to connect

Test Double Executive Leadership Team

Learn about our team

Like what we have to say about building great software and great teams?