Microspeak: Breaking into jail
In Microspeak, breaking into jail is an idiom that has the general sense of admitting to or possibly even creating problem by opening your mouth. The metaphor here is that you are safely outside jail, but you are for some inexplicable reason taking active steps to get yourself inside. (Remember, Microspeak is not just terms used exclusively within Microsoft, but also terms used at Microsoft more often than in the general population.)
One example of breaking into jail is saying something in a meeting that makes it sound like you are taking responsibility for a problem that is not yours.
We don’t want to break into jail on the problem of how to repair systems that are already affected.
In this hypothetical example, the team is working on a way to prevent the problem from spreading. But they don’t want to be made responsible for repairing the systems that are already affected, so they are being careful not to bring up that topic, or at least making sure that when they bring up the topic, they make it clear that it is not something they will be taking on.
Another example of breaking into jail is volunteering information that could get you into trouble.
I may be breaking into jail here, but how should we classify work items whose projected completion date is after code complete?
The person asking the question is implicitly admitting that they have work items that extend beyond code complete, seeing as they’re asking a question about what to do with them. This is probably not good news, seeing as it shows that you are going to miss your delivery dates. On the other hand, it demonstrates honesty and accountability, so this type of “breaking into jail” is usually viewed positively. It’s better to fess up to your problems sooner rather than later. We don’t want to engage the entire team in a game of schedule chicken.
Bonus chatter: It seems that there are some dialectic variations on this concept within Microsoft. One that I found particularly amusing was the idiom “Keep the 💩 in the horse.”