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When transitioning a new team to a highly iterative planning process (where we plan and complete work in weekly Task Cycles) one question I always have to ask is: "When do we want to start and end the weekly Test Cycle?" The answer I almost always get is, "Monday and Friday," to which I typically reply: "How about Wednesday?"
Teams like to think of the workweek as a natural candidate for short iterations, Task Cycles, or other timebox structures. Why not? Each workweek is a well-understood time period bookended by weekends. Initially the idea seems to make a lot of sense.
But using the traditional Monday to Friday workweek as a timebox structure has numerous drawbacks. First, in order to accurately map Task Cycles to workweeks you actually need to meet twice a week: once on Monday to open a Task Cycle and again on Friday to close it. And what do you do between these meetings when no work is planned? Unless, of course, these meetings are the last thing everyone does on Friday and the first thing everyone does on Monday. But that doesn't sound very practical (or very fun) so perhaps we do need to adjust our definition of a workweek a little bit and have just one meeting on Monday morning to both close out the previous Task Cycle and plan the next. That gives everyone the weekend to try to catch up on and complete their tasks (like I don't have anything else to do on the weekend). And, as an added benefit, we can all meet bright and early at 9 am on Monday morning to talk about what we did last week and plan for this week because we all love nothing more than Monday morning meetings. With donuts. Ah, yes, nothin' like Monday morning status meetings and donuts.
And it only gets worse. After a couple of months you begin to realize that most holidays seem to land on Mondays and Fridays, selfish team members continue to take Mondays or Fridays as vacation days to create three or four day weekends, and self-absorbed traveling team members continue to arrive late on Monday and leave early on Friday to make flights to--of all places--home. Sarcasm aside, all these things really do make standing meetings on Monday or Friday difficult to maintain.
The solution? Pick a day in the middle of the week, like Tuesday, Wednesday or Thursday. Even better, have the meeting in the middle of the day, like 11 am or 2 pm. Make you current Task Cycle (or iteration or whatever) end at this meeting, and start the next one at this same meeting. I would argue that this is, in fact, what many established teams ultimately do, although some never stopped to think about why their meetings bounced around between Monday and Friday until finally settling in on Tuesdays at 2 pm. I would also argue that status meetings on Monday and Friday is a classic mistake for new managers and newly-formed teams. A mistake that, if avoided, can save organizational effort, avoid unnecessary frustration, and leave teams with more time to spend on adopting other agile practices and techniques.
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