Time Spent On Planning

Last week, I shared a bit about my annual review. One of my thoughts coming out of my annual review was that I felt like it took too long for me to complete.

If I recall correctly, my review took me about 4 days to complete. Doing the math, this works out to be approximately 1% of the year.

In a conversation with Shirley, I started reflecting on whether my judgement was fair–is it really that bad to have spent 4 days on my annual retro and planning?

Reflecting on projects at work, we seem to spend significantly more time on project planning and project retrospectives. From this perspective, it actually feels sort of absurd if I put a constraint on project planning and retrospectives to be less than 1% of the time. At that point, I’d really be questioning if we’d put in the valuable effort into:

• learning what worked previously and how we can do more of that
• learning what didn’t work previously and what we can do instead
• understanding the problem we want to solve
• understanding why that problem is important to solve
• understanding what we want to do to solve the problem
• understanding how we’re going to execute on that solution
• reflecting on potential challenges we may face and what we could do in response
• (et cetera)

At the same time, this estimation for how much time I’m spending on planning and retrospectives isn’t complete. I do spent time throughout the year on my monthly and quarterly reviews which allow me to refocus on my annual vision, and also (along with my weekly reviews) learn from the past.

I’m also experimenting with including a transcluded block of my monthly vision in my daily note template. Ideally, this means I’m re-reading and re-presenting my vision each day; in reality, I do skip this on those days I feel the most flustered (probably the most important days I remain aligned with my vision though 🤣).

And that alignment with the vision is what’s truly important.

Maybe that’s why it requires more planning and retrospective time for work projects–alignment is more difficult to achieve when there are multiple people involved. Having multiple people creates additional complexity through different perspectives, motivations, expectations, communication styles, values, etc.

And maybe that means I should focus less on judging whether I’m spending too much time planning, or judging where the line for spending too much time planning is. Maybe I should stop the judgements and just reflect on whether this amount of planning is still effective, useful, and serving me.