Writing on product management, knowledge work, and personal productivity. First-person, opinionated, written for mid-to-senior PMs navigating real environments.
The product management job in the books isn’t the one many of us actually do. The books describe outcome ownership. Your calendar shows dependency syncs, status decks, and dates you never committed to. That gap has a name, most organizations won’t say it out loud, and reading it as personal failure is one of the most expensive mistakes you can make in this career.
Most product teams think prioritization is about choosing what to do next. It isn’t exclusively that. It also means giving your team explicit permission to let say no and to let things die. And if you can’t point to the list when someone asks why something isn’t moving, you don’t have priorities. You have a wish list.
The most dangerous organizational failures aren’t the ones that escalated and were mishandled. They’re the ones that never surfaced at all, because PMs learned, through repeated experience, that escalating certain categories of risk reliably damaged their standing more than absorbing the consequences quietly. When a PM stops escalating, they aren’t being resilient. They’re revealing that the organization has trained them that visibility is punishing. And that means leadership is flying blind by design.
People don’t fail to document because they’re busy or undisciplined. They fail to document because institutional knowledge is leverage, and documentation surrenders it. This is the third time I’ve written about incentive structures hiding behind individual behavior. The pattern keeps showing up because organizations keep misdiagnosing it.
Has discovery ever killed a feature at your company? Not delayed one. Not reshaped one around the edges. Killed one. The answer tells you everything. Every product team I’ve worked with in the last five years runs continuous discovery. Weekly customer interviews, opportunity solution trees on the wall, synthesis sessions in the calendar. And in almost every case, the actual product decisions still get made by whoever holds the most organizational authority in the room.
Someone in a post-mortem always says it: “Why didn’t anyone flag this?” The risk register exists to make that sentence unsayable. Not because it tracks risks, every project does that informally, but because it forces the people in the room to say, on the record, what they plan to do about them. That’s not an organizational function. It’s a political one. And most PMs are using it wrong because they’ve never understood what it actually is.
In my first years in product management, I had all the tools: Jira boards, sprint backlogs, wiki pages, stakeholder decks. Yet the same conversations kept recurring. About priorities. About why we’d dropped things. When I mapped two sprints of actual work against the type of contribution each task made, the pattern was obvious. I wasn’t overloaded. I was unbalanced. The category I was systematically ignoring was Clarity — the one that makes every other type of work more effective.
I often walk into a planning session knowing that a significant portion of my team’s capacity is already spoken for. Not by features. Not by tech debt. By compliance. And when I present a roadmap that reflects this reality, colleagues look at it and ask: “Why is Q2 so thin?” It isn’t thin. It’s honest. But most roadmaps in regulated industries aren’t.
In December 2022, my team at Trusted Shops killed the biggest feature of the year. Not because it stopped working. Because it worked too well on the wrong axis. We had pushed review questionnaire conversion up by a huge percentage. Internally, the win of the year. Three months later, we rolled it back. We learned that the volume of negative reviews mattered more to our customers than the volume of reviews overall.
Most product teams I’ve worked with believe they have a strategy. They can talk about it in meetings, reference it in planning sessions, and nod along when leadership mentions it. But when I ask a simple question, “Can you show it to me?”, the room gets quiet. That silence tells me more about the state of a product organization than any roadmap ever could.