Do you remember that telephone game we used to play as kids on the bus. This was where someone sitting at the front would make up a phrase and whisper in the ear of the person sitting next to them, and then that person would take what they heard and pass it along and so on. By the end the last person to hear the phrase would say what they heard and would compare it to what was originally said. What the last person ending up hearing was always drastically different. Basically the message ended up getting lost in translation. This is the way I feel about status reporting.
I always seem to be working on improving my time management and personal organization. Right now it's 1 AM in the morning and I am writing this, and I suppose I should be sleeping. So why create a status report? Well I grew up thinking it was to cover your rear, or tell your boss you were doing something. It's quite the opposite actually, at least for me. More on this later.
Like many there are days where I just feel that I wasn't productive. Why? Is it' the number of things that were accomplished? Is it how hard they were? Or maybe they just weren't fun tasks to complete in the first place. Recording isn't necessary fun, but it gives you data and more so some history. This data you can study and react to how you see fit.
What you want to report on is up to you, your project and your own context. It's not the same for everyone and you should make it your own. Right now my current role is as an "Evangelist". Compared to my previous roles, it's much more free form than the past 12 years where I was producing product for customers. These are the current sections I log to in order:
* This is just my overall summary of the week and how I felt about it.  If no one else was to look any further down they should have a pretty good feeling about what got done. This is always less than 3 paragraphs. Usually just 1\.* General Activities Completed This Week * Now this section and the following two have changed over time. For me I think about a large majority of my tasks as General, Community and Customer related. I just bullet out in one sentence what the items which were accomplished.* Community Activities* Customer Activities* Unplanned Activities * **<u>This is one of the most important sections for me</u>.** We all get interrupted, so capture it. Here is where I log all of those items which will end up pushing planned work off the stack.* Content Produced * I produce content, I like to have a list of it.* Activities Planned For Next Week * Just a bulleted list of items to accomplish for the week.  This could be listed by day, but each day I restack rank my tasks and knock stuff out.* Upcoming Community Events * As part of work we always have important dates. Maybe it's a beta release or a speaking event. I look at this section as milestone dates that I will be actively involved in. It's my "front log" to look at when I am planning my upcoming week(s).* Upcoming Out Of Office * Plan to take time off, PERIOD.
I think it's important to note that these continue to change. When I am doing formal product development I have an entire section on what features have been closed as well as the stack rank for the next features. Make it yours, at the end of the day it's a planning tool for you.
Short answer, somewhat during the week, first thing Monday for sure.
I try to keep my lists up to date as things come up. I have enough to try and remember from day to day I don't need to worry about trying to remember the details of my status report. First thing Monday morning I not only finish it and communicate it but plan out what I am doing for that week.
I mostly live the digital dream, but I do religiously carry around a Moleskine notebook. My status reports are nothing fancy, they are Work docs. Sure it could be some complicated web site with some awesome UX that could print reports and slice bread, but why? Word works for me so I am cool with it.
Back to the Moleskine. I use this daily. For me my Moleskine is where I drop my thoughts, ideas, sketches and run my daily task lists. Sure there is a bit of overlap between the two but there is something ( for me ) about the physical act of writing that allows me to get my thoughts in better order. It also helps me take the psychic weight off my chest, so I can concentrate on the task at hand. Seems silly but start writing your stuff down in a Moleskine and you will see.
I guess you could say my Moleskine is my active record while my Word documents are more of a polished set of formal documentation.
But what about notecards? I love the Agile movement. It works and while not for everyone there are aspects that are hard to refute no matter how opinionated. Notecards are one of them. Whenever I have a hard time trying to sort out WTF I am supposed to get done I get out my stack of cards and start laying them out then sort from top down. Works every time.
Again no later than Monday AM everything is formally done in Word and the week begins.
My Ah Ha Moment
After years of thinking status reports were just for covering your rear in the back stabbing corporate world, it dawned on me that I was actually getting use out of this exercise. It wasn't about the piece of paper it was about creating iterations and stack ranking. It was about doing an iteration review with myself and later doing a customer review with my peers or boss. I was finding myself feeling good about the things I accomplished while knowing what the next week entailing. I found myself comparing my current status against my 6 month and years plans\goals. This felt good and I was starting to feel more organized.
This has become so important, I don't even think of all this as status reporting but my own iteration review with the added bonus on having some formal documentation I can share with my peers and management.