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Latest Newsletter Articles

  • Simplifying Interactions with Honesty

    I still remember my first ever in-person interaction with Matt Mullenweg, the CEO of Automattic. It was at a Grand Meetup in Park City. Matt stood directly behind me in the lunch line. I knew that this was my moment to say something. About the only thing that I knew about him at the time…

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  • Closed mouths don’t get fed

    Closed mouths don’t get fed. I’m not sure when I started to internalize this or where I initially read it. But, it’s something that has stuck with me for some time. Phrased differently, one might use: You don’t get what you don’t ask for. Or: What’s the worst that can happen? You get told “no”?…

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  • You’re all designers

    At a recent Automattic meetup I led a session between WordPress.com designers and engineers. As part of these discussions, the topic of roles and responsibilities came up. Specifically, some engineers were questioning whether they should also be product owners or analyze data. My response to this was probably a bit long winded, but was roughly…

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  • Have you tried it to see what breaks?

    Last year, my team received a challenge from our CEO to try to significantly improve our purchase flow along with a bit of time pressure. For several months, I’d had a good, high-level idea of how we might improve our purchase flow. But, as the idea lacked concrete implementation details, we kept prioritizing other work…

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