Tag: Product Management


  • We trusted our anecdotes until we had to count

    For a long time, I could have told you good stories about the quality of our software. We talk to customers before we build, reviews catch problems early, and critical bugs get fixed fast. What I could not have shown you were software quality metrics that backed any of this up. That changed when our…

  • We made the same call as the customer who left us

    On the last Monday of September, I saw the same build vs buy decision from both sides of the table, a few hours apart. In the morning, one of our customers called to say they would end a service we run for them. From January, a team elsewhere in their group would have spare capacity,…

  • A Revenue Plan Is Not a Strategy

    For my last coaching session, I brought a list of questions about our team setup. One product manager wants to move to our managed service, so who takes over the areas that become free? My coach listened and then said that all of it was tactics and that the business strategy behind it was missing:…

  • When Building Gets Faster Than Learning

    As implementation gets faster and cheaper, the bottleneck in product development can shift toward product management and design. Engineers can turn an idea into working software while the team is still figuring out which problem matters, how people will use the solution, and whether anyone will pay for it. Product and Design Are Getting Faster…

  • Reproducibility Matters More Than Scalability

    For the past two years, the loudest debates inside our company have used the same vocabulary: scale, productivity, AI. Every quarter delivered a fresh version of the same conversation. How do we scale sales? How do we make customer success more productive? Which AI tool takes which workload off whose desk? The vocabulary came from…

  • Losing an Enterprise Deal: How to Tell Your Team

    An enterprise customer we had built toward for months backed out, late and without warning. The gut punch lasted twenty minutes. What mattered was the next few hours: what we told a team of forty, and in what order. Here is the playbook, and where we went off script.

  • Encoding Judgment Is Not a Writing Problem

    Turning how your best people work into an AI Skill sounds like a documentation job. It isn’t. The hard part is judgment, and the moment you try to write it down you hit a forty-year-old problem that AI has quietly moved rather than solved: the work is no longer getting the knowledge out, it is…

  • Two Patterns of Great Product People

    Over the past couple of years, I have had a few product people on my team, received coaching myself, and picked up a lot from conversations with other PMs, founders, and people who think deeply about building products. The contexts are always different. Different industries, team sizes, stages. But two patterns keep coming up with…

  • Product Team Collaboration

    In my last blog post, “The Framework Trap,” I talked about all the problems we ran into when engineers, designers, and product team members were working together. I’ve come to see that Scrum, with its strong emphasis on the right processes, has actually been more of a hindrance than a help to our team. While…

  • The Framework Trap

    When we started working on our products, especially our software, we had a pretty inexperienced team. Some of us had already worked on software projects at other companies or participated in research projects at universities or research institutions. The team’s most experienced member, in terms of years of professional experience, was a software engineer with…