Today I was speaking with a CTO at a PE firm who has seen it all. He got in trouble at many portfolio companies for asking why things were done a certain way, because when he explored, there was not a good answer on the other side.

I was reminded that I've always needed to know the why, but being in the weeds of this entrepreneur thing makes me forget to ask that at my own org. Why does everyone default to using Jira and Confluence? Why not Shortcut and Notion? Why not something else entirely? And, even more fundamentally, why sprints?

When I think about my dream team, I envision 3 Full Stack Product Engineers that basically act as product owners for 30% of the time, and full stack engineers the other time. They act as a team lead sometimes, but defer to the BE and FE devs on their team when the time is right. Just a small team; in the case of a UX/UI product - 1 Full Stack, 1 Backend, 1 Frontend and among the 3 of them, they delegate to get the job done and unblock each other as necessary. No sprints within the team. No tasks within the team, just self organizing, aligned on the next milestone in front of them. The org losely has a high level "sprint", i.e. this feature or feature set will be done in the next two weeks, but really day to day has no tickets, just people plugged in and going.