• Forgot to figure out edge cases when shipping the new search.
  • Did not think about Keyboard binding for Search.
  • While shipping the Poll feature, missed a few acceptance criteria for the sidebar.
  • Left a trailing comma in the Poll feature copy. Should have got Design involved in the sign off process.
  • While releasing mailcast - a mailing list product, forgot to let guests opt-in first. This feature would have become a favorite for spammers. Thankfully this was pointed out by the CEO.
  • While building Flock support was initially very dismissive of CTO’s idea to just build Support bots inside Flock and not a standalone app. Wasted a month on the detailed spec and mocks before realizing bots would work fine as an MVP. Instead of a 6 months timeline, we managed to ship the v1 of Support in 2 weeks.
  • Never sent out release emails.
  • Missed iframe resizing on attachments in Search. Should have spent more time with devs on ironing out the implementation details.
  • Polls did not do as well as I had thought. I should have spent more time in the WHY than deciding to spend months building out a better polling feature.
  • We misattributed a decrease in a metric chat tab IA change while the tracking was broken. Should have tested metrics on integration before shipping the IA change to production.
  • Got super happy seeing search % increase post a revamp. The real reason was analytics events firing multiple times from the backend for a single event. Again, I should have tested metrics more on integration.
  • Did not work enough on the discovery of existing features. The focus was more on releasing new things.
  • I was passionate and disrespected people that I thought were not passionate enough. Led to a lot of broken relationships.
  • By the end of my time I was burned out and was low energy. As a PM you have to be in high spirit and always bring your A-game. You can’t afford to look like you are demotivated.
  • Did not create a detailed charter. Instead of focusing on more features and more experiments, we should have spent more time thinking about where we want to be after X years.
  • I was always trying to prove my dev credentials and spent far more time discussing tech implementation details than working on the next set of problems to fix.
  • I did not know how to say NO diplomatically.
  • Multiple incidents where I could have shut my mouth, let things calm down, but because of my ego escalated trivial issues that had no impact on our end customer.
  • I focused a lot on what features can improve retention, comparing all the existing features we had, instead of thinking what could be a game changer for us. Incremental features will never help you gain market share.

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