PRODUCTHEAD: Ending the enshittification era
PRODUCTHEAD is a regular newsletter of product management goodness,
curated by Jock Busuttil.
product by product (caribou rmx) #
every PRODUCTHEAD edition is online for you to refer back to
tl;dr
Fight enshittification by encouraging interoperability and openness in your product ecosystem
You can prove a concept by building something janky and cheap that shows it working for real
OKRs do not exist in isolation – context, strategy and culture set the scene
hello
Welcome back! Let’s dive back in.
You’ve probably heard the phrase ‘enshittification’, as coined by Cory Doctorow to describe how tech products become tangibly worse over time. In a recent talk, he explains why products decay over time, something we as product managers may be all too aware of. What’s perhaps more interesting is how Cory attributes the causes of this modern trend to changes in policy affecting tech companies, such as the weakening of competition law and suppression of interoperability.
Tom Kerwin and Corissa Nunn write about why it’s important for founders and intrapreneurs to build something janky to prove that their concept works, rather than simply banging on about the possible future vision. It’s ‘show, don’t tell’ updated for the vibe coding age.
John Cutler is thinking about why your organisation is structured the way it is, and how that affects how it operates. Based on his interviews, he describes the patterns he’s observed, and offers concise advice on how to survive, thrive and hack the system you find yourself in.
And to finish up this week, Martin Eriksson offers 11 reasons why your OKRs (objectives and key results) are broken. Perhaps they’re not the right fit for your organisation, and something else may work better. But overall, don’t blindly copy frameworks and methodologies from other organisations. Context, culture and strategy all shape the approach you need to take – and aspects of them change over time – so instead create a system of measuring what matters that is specific to your organisation.
Speak to you soon,
Jock
what to think about this week
How Enshittification Conquered the 21st Century and How We Can Overthrow It
Enshittification swept through the digital world over the past decade, and it has only accelerated since, as everything—grocery stores, nursing agencies, even public schools—migrated to the Cloud and became digital services. The more digital something is, the more vulnerable it is to enshittification—and when your data is in someone else’s Cloud, it’s that much easier for the cloud provider to turn the screws on you: locking you in, raising prices, tying services.
[VIDEO] How to build a better internet
[Cory Doctorow / CloudFest 2025]
The paths to proof
A founder we’re working with saw his development roadmap stretching out over the next couple of months. And this ain’t his first rodeo. So he knows that even though he’s on the right track with his idea, it would still be very easy to build something that doesn’t work for his market. So he asked us, “how can we test this idea right now? I don’t want to risk wasting the next 8 weeks”.
[Tom Kerwin & Corissa Nunn / The Reach]
Why Are We Organized Like This?
This post is about understanding why your company is organized and designed the way it is. Which of these nine patterns looks familiar?
‘Game of Thrones’ or ‘Thoughful Transformation’?
[John Cutler / The Beautiful Mess]
Why Your OKRs Are Broken
Research shows 60% of organisations fail at OKRs. Here are the 11 reasons why—and how to avoid turning a great tool into an elaborate to-do list.
OKRs built on shaky strategic foundations don’t work
[Martin Eriksson / The Decision Stack]
recent posts
Are developers vibe coding themselves out of a job?
And is the increasing reliance by junior developers on AI coding assistants storing up a generational skills shortage for the future – ‘professional debt’, if you will?
So simple, anyone could do it. Wait – don’t fire me
[I Manage Products]
Cloud computing for non-technical product managers
To understand how cloud computing works, we’re going to start with the basic building blocks and work our way up.
And why is it a cloud anyway? (All is revealed)
[I Manage Products]
Navigating your product management career
Ross Webb and I have been chatting about product management career progression.
We cover topics including:
» Thinking of visibility as a strategic competency, not self-promotion
» Controlling your narrative through regular updates
» Building cross-organisational relationships deliberately
» Mapping your stakeholders’ preferred communication styles
A roundtable chat on moving into product leadership
[I Manage Products]
can we help you?
Product People is a product management services company. We can help you through consultancy, training and coaching. Just contact us if you need our help!
Helping people build better products, more successfully, since 2012.
PRODUCTHEAD is a newsletter for product people of all varieties, and is lovingly crafted from a ticket for the Radiohead lottery.

