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I'm leading a project for the first time and feel like it could have gone better.

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Software Engineer at Series A Startup2 years ago

I'm driving a project with ~5 engineers. Even though we're on track to make it now, the initial road was somewhat rocky. We had to go through a lot of conversations to get execution started, spending ~50% of the allotted time on planning and alignment. This led to scope being reduced for v1 and us building less features that we would have liked.

As a startup, I know that we should be moving faster - What's the best way to handle the project from here and how can I improve in this area in the future?

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    Robinhood, Meta, Course Hero, PayPal
    2 years ago

    I'll split my advice here into 2 overall schools of thought: What you can do in the short-term and what you could do in the longer-term.

    Short Term

    • Of course, ship the project first. After it's done, I recommend doing a retro (short for retrospective), which is a formal meeting where the team looks back on the project and tries to learn from it. This is what I talk with my teams about in retros:
      • What went well
      • What didn't go so well
      • What can we do in the future to get better
    • However, startups, especially a Series A one, need to move fast. If people don't want another meeting, that's perfectly fine. I recommend just making that retro doc on your own (shouldn't take more than 1 - 2 hours) and then sharing it out with the team to get feedback and alignment on the suggested future action items in particular.

    Longer Term

    These are just some ideas from me; the best thing to do is work with your team to figure these out.

    • Time-box planning so it's only 10-25% (these numbers are random/rough from me, talk to your team to get better ones) of the overall timeline, and make sure everyone agrees on this baseline. During project execution, work backwards from this time allotment and amp up accordingly. Let's say you need to finish planning in 2 days and there's still a lot of alignment needed: It's time to drop more meetings probably and have more 1:1s with outlying stakeholders.
    • If you're not doing it already, create a large, massive, "source of truth" planning document for any meaty project you take on. Whenever any alignment discussion is had, make sure that the information is also put there so keep everyone on the same page. I've found these central docs to be really useful in planning.

    These are not entirely connected, but I recommend checking these out as well if you have the time:

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