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  1. Nobody Majors in Transformation

    When people ask me how to get into transformation work, I usually have to start by admitting that I did not get into it on purpose.

  2. I have spent most of my career telling people that if you do the work right, the outcomes follow, and for a long time I believed that was the whole story.

  3. When It's Actually Their Money

    I've now worked inside very nearly every funding model there is, and they each leave a mark on how you think.

  4. I have watched the same thing happen enough times now that I have stopped being surprised by it, which is its own kind of sad.

  5. Real Time Is Table Stakes

    For most of my career, the holy grail in data was real time, and everyone in the field chased it.

  6. Measured to Fail

    There is a statistic that gets quoted in almost every conversation about digital transformation, the one that says seventy percent of them fail, and I have heard it repeated so many times, in so many rooms, that it has stopped functioning as a fact and st…

  7. Start With the Org Chart

    When I step into a new role, the first thing I do is go wide, fast, and the document I reach for before almost anything else is the org chart, because that single page tells me more about how a company actually behaves than any deck or strategy memo ever…

  8. Could One Person and AI Build the Whole Thing?

    Rainfall cleared the App Store today, which is a nice sentence to be able to write, but the approval was never really the thing I was testing.

  9. The Definition of Done

    I have been building my own things lately, partly because I have always wanted to, and partly because anything I build might one day be worth something to someone else.

  10. The Red Flags That Are Actually Green Flags

    A couple of years ago I was on the buying side of this exact problem, and I want to start there, because it is the part I think about most now that the situation has reversed itself on me.

  11. When a company decides that its sales force could be doing better, the proposed fix is almost always the same thing, and it's almost always delivered with total confidence.

  12. Don't Boil the Ocean. Find the Case.

    When I describe the data problem we inherited at Southern Glazer's, people tend to assume I'm exaggerating it for effect, and I'm not.

  13. The Distributor Became a Media Company

    When I describe what we built at Southern Glazer's, the line that lands hardest with people outside the beverage-alcohol world is the one that sounds least likely on its face.

  14. The integration of AI into enterprise engineering is genuinely reshaping how organizations manage their product development teams.

  15. At a company I worked with earlier in my career, someone made an observation in a meeting that I have genuinely never been able to forget.

  16. Why I Stopped Running Projects

    The trouble with projects, the thing I kept running into for years before I could name it cleanly, is that they end, and the uncomfortable truth is that not everything should.

  17. When Proof launched, our sales team was fairly convinced it was there to replace them, and the honest thing to say is that they were not wrong to worry.

  18. Tech Is Dumb Out of the Gate

    There is a warehouse worker I keep thinking about, long after the project that introduced me to his story has ended.

  19. As we navigate the complexity of engineering, product development, and digital transformation, it is easy to find ourselves trapped in a cycle of relentless problem-solving.

  20. Why I Keep Revenue Goals Out of My Vision

    Nearly every business book I have ever read puts a revenue goal squarely inside the vision, and I have come to do the opposite.