Wisdom
You don’t involve Winston Wolf if you have a "strategy." You call Winston Wolf to handle a messy shit sandwich and after it's handled, Winston Wolf does not call you back or visit you. And product managers around the world are nodding their heads right now.
Product
Faith-based product development runs on one belief: that a leader's confidence can substitute for a plan. Here's how to spot the symptoms before the gap between the story and the schedule collapses on you.
Product
Toxic product management isn't rare — it's just rarely named. After watching one particularly bad case unfold firsthand, here's what actually lets unsuited PMs into roles where they can do real damage.
Product
Substack shipped a scanner to catch AI writing, on a platform whose own growth playbook spent two years rewarding the exact posting volume now under suspicion. A look at what happens when you build enforcement for a problem your incentive structure created — and never touch the incentive.
Product
What a Senate campaign in Maine can teach you about proxy metrics, buyer/user splits, and shipping without QA, yeah, Product Management is a lifestyle
tech
Everyone's calling the AI buildout 'industrial.' A fiberglass plant and a photomask shop are both industrial — and only one of them can fund itself.
Product
AI isn't disrupting product management as a category. It's disrupting the execution layer of it specifically. If you've been telling yourself you're on the strategic side of that line, this post is about whether that's true.
Tales and tips from a lifetime of Product Management
The title survived. The ceremonies survived. The Jira boards are still getting groomed. What didn't survive: the function that made product management worth having in the first place. A diagnosis.
Part 4: The promise bifurcated, and many were sold a bill of goods. For most, the grind of the feature factory was lived experience
Or, this is the removal of the Cargo Cult technocrats, hired to work, but not to have a purpose. You surely have come across these drones.
We've been tracing an argument across this series. Post 1 went back to the industrial-era construction of the white-collar professional identity. Post 2 followed that architecture into Silicon Valley, where it got turbocharged with founder mythology and libertarian individualism. Today we get to the mechanisms that
Having set the table in the first installment of this, let's talk about how the California environment paved the way for an anti-organising mindset
Tech in general is very resistant to organizing. As we enter the AI age, it seems like this missed opportunity will haunt the industry. A look at how this began (a series)
Or: how the AI ecosystem is running the oldest con in tech, and why so many product managers are apparently fine with that
(or: how we quietly dismantled the one role that understood the whole business)
What a gallon of gas can teach you about anchoring, asymmetry, and the stubborn math of consumer behavior
What it gets right, what it gets wrong, and how to use it without getting torched. There is no doubt that AI can greatly augment your work, and help you get to defensible positions without getting bogged into the tactical morass
My near three decades in the product management trenches has reinforced that product management isn't a recipe, it is a craft, and it is a craft honed by repetition and practice.
Product management has transformed significantly in my 3 decades of experience, but it has still remained true to its original goals: how to meld business context to solving customer problems