A career across the full breadth of IT.

AI-generated software has changed what “unfinished” looks like.

Human-built systems usually show their missing pieces: the button does nothing, the endpoint is absent, the report is still an optimistic rectangle.

AI can produce something polished, tested, and demo-ready while hiding a much deeper gap. It looks 90% complete until the first real user discovers that the remaining 10% includes the foundations.

That changes the engineering leader’s job. Progress can no longer be judged mainly by visible features or passing tests. We need deliberate adversarial checks, real workflows, and engineers who understand enough of the system to distrust a convincing demo.

How are your teams distinguishing software that looks finished from software that can safely evolve?

Source: The Chasm: The Shape of Unfinished AI Codebases — https://jimmyhmiller.com/shape-of-unfinished-ai-codebases

#CTOThoughts #AIEngineering

Building pricing software: “Make it flexible enough for every pricing model and data structure - but simple enough to use without a manual”.

Configurable software creates an interesting paradox.

It is usually harder for vendors to build, test and maintain. Every additional rule, dependency and exception creates more possible combinations - and more opportunities for something to break.

But pricing is rarely simple

Different markets, customer segments, contracts, currencies and approval levels all introduce legitimate complexity.

So, what happens when pricing software is not configurable enough?

The complexity does not disappear. It moves somewhere else:

• Pricing rules and up in spreadsheets
• Exceptions are managed through email and Slack
• Every change becomes an engineering request
• Critical knowledge lives in the heads of a few people

The goal should no be to eliminate complexity. It should be to put it in a system twhere it can be tested, governed and understood.

Configurable software is technically harder to build, but usually better for pricing teams.

Because if your pricing platform cannot represent how your business actually prices … is it simplifying the work, or simply hiding it?

hashtag#CTOThoughts hashtag#PricingTechnology

The bugs I worry about most are the ones I’ve already learned to work around.

Use a product every day and its oddities become muscle memory: click here first, refresh after that, avoid this sequence entirely. Eventually, I stop seeing friction and start seeing “how the product works”. The user, inconveniently, has not attended the same training.

That is what I’m trying to get better at noticing. Dogfooding is useful, but familiarity can hide exactly what it is meant to reveal.

I need to watch new users more closely, write down the “little tricks,” and resist answering problems with “just do this”.

Which workaround has become so normal in your product that nobody calls it a bug anymore?

Inspired by the article Bug blindness - https://danluu.com/bug-blind/

#CTOThoughts #ProductQuality