Writing
Long-form writing about decisions, constraints, evidence, and what changed when the first answer did not hold.
Long-form archive 30
- The name changed. Here is what it is now and how it's actually going.This newsletter used to be called Product of One, and it was about career strategy. It is now called The Operator Economy, and it is about building businesses that one experienced person can own and run.
- The Four-Minute NoIt took her four minutes to decide not to apply.
- The 90% match that never calls backA product director I've been advising sent me two links back in June. A job description, and his resume. "I'm at ninety percent on this," he said. "Maybe higher." He'd gone through the JD line by line. Roadmap ownership, check. Cross-functional leadership, check. B2B SaaS, ten years of it. He applied the same afternoon.
- The intro that took two years to set upA guy I used to work with messaged me in March. He'd just been laid off. Director level, fifteen years in, the kind of background that's supposed to open doors on its own. He wanted to know who I knew at three companies he was targeting, and whether I'd put in a word.
- The Feature Nobody UsedI shipped a feature nobody used because I never watched anyone use the thing it was supposed to fix.
- The Generalist TrapA guy I've been talking to described himself as a generalist three times in one call. He meant it as a strength. He'd done product, ops, some sales, a stretch running support. Fifteen years of being the person who could do whatever the company needed.
- What 'More Senior' HidI once told a candidate we went with someone more senior. It wasn't true.
- Apologizing For Your Own BackgroundShe apologized before I'd read a single line.
- Two Reads of One CandidateTwo of us walked out of the same interview with opposite reads on the same person.
- You're Talking to the Wrong PersonA guy I'd connected with a few weeks back sent me his outreach list to look over. Twelve names. Eleven of them were recruiters.
- What Changes When You Stop ApplyingThree weeks ago a customer success director I've been advising sent me a screenshot of her LinkedIn DMs.
- The five-minute application filter"Should I spend my Saturday on this?"
- Why Six Months of Applications Stops WorkingLast quarter I sat on a hiring panel for a Director-level role. Forty-seven applications hit the posting in the first three days. The panel reviewed seven of them. Of the seven we reviewed, six had a warm introduction from somebody already in the company. The seventh got in through a Slack channel where someone had shared the resume directly. None of the other forty arrived through the official funnel and made it into the room.
- Fix the sound of the oceanA guest at the hotel I ran in Mexico once asked me to fix the sound of the ocean.
- Thorough Onboarding, Empty CompletionI built my product's onboarding to be thorough. Then I watched people quit it halfway through.
- The translation gapI've spent the last few months in deep conversations with people in active career transitions. Senior PMs, operations leaders, mid-career executives, founders pivoting back to operating roles. Different industries, different stages, different reasons for moving.
- Vague Feedback Is a VerdictI kept someone on my team six months longer than I should have.
- Six Months Too LongI kept someone on my team six months longer than I should have.
- The Resume A/B TestSomeone I interviewed for research ran an A/B test on his own resume.
- What I Got Wrong About Sending MoreFor five years I told people the answer was send more.
- Activity Versus Outcome in a Senior SearchA senior PM I've been talking to applied to 80 roles in the first quarter of this year. She's at a level where the median time to a new role is 9 to 12 months, and she had a fixed runway. So she did what felt productive: more applications.
- The deposit before the withdrawalTwo weeks back I wrote about a senior IT leader I've been talking to. Twenty-two years in. Eight months into a search with no interviews from cold applications. The one interview that came close, the one where he made it to a final round, came from a former colleague who walked his resume into a hiring manager's office.
- What 'Overqualified' MeantI interviewed a VP candidate once who was perfect for the role on paper. More experience than we needed, a deeper technical background, and had managed teams twice the size of ours.
- Why the best career tool isn't a generatorRun your resume through ChatGPT and you'll get back something that's technically better. Stronger verbs. Tighter structure. Keywords matched to the job description. And it won't sound like you at all.
- Nice vs. kindThere's a difference between being nice and being kind, and I think about it constantly when I'm building.
- AI Usage Excellence FrameworkThe AI Usage Excellence Framework provides a structured pathway for product managers to evolve their AI collaboration from basic task automation to sophisticated cognitive partnership. This framework emphasizes intentional, progressive integration of AI tools to enhance—not replace—human judgment and creativity.
- An Open LetterYou've sat through the vendor demos.
- Decision-Driven DevelopmentDecision-Driven Development (DDD) is a framework that transforms how product teams approach their work. Instead of focusing on activities and deliverables, DDD ensures that every piece of work directly enables a critical product decision.
- Prompting Is Overrated. Context Is Everything.Everyone's talking about prompting. There are courses on "prompt engineering." LinkedIn is full of "10 prompts that will change your life." People are building entire businesses around teaching you to talk to AI.
- Sprint Metrics & HealthThe Sprint Metrics & Health Framework provides a systematic approach to tracking sprint performance and team wellbeing. It combines quantitative metrics with qualitative health indicators to create an early warning system that helps teams maintain sustainable pace and predictable delivery.