Should You Let Your Boss Inside the Box?

Andre has, yet again, inspired another post. On my last post that discussed a quick way to remind others without remembering to, he commented:

You might want to create a shared Google Calendar, adding your boss’ email address, then letting him know about the calendar.

I have a long history of trying to get my bosses to adopt parts of my system. The problem I've run into is that they're much the same as other people in that they don't want to change, and, sadly, they're in the position such that they have others, like myself, that run things for them.

You really have to make a strong sell to them that what you're asking them to do is a better system than the one they already have - "if it ain't broke, don't fix it" seems to be the operative rule. That they're taking up your time and mental energy does not figure in to the system being broke.

There's this other thing: I'm a Black Box worker. For those of you unfamiliar with this term, watch Merlin's video about it (it starts around 8:30 and relevant parts until around 10ish). After the jump, I'll go on.

I have multiple bosses wanting different things, and they don't care what happens inside there. My experience is much like Merlin's: they'd rather not hear about the mental sausage.

But on the occasions I've let bosses inside the box, there has been an unintended side effect - they start asking questions and wanting to change things inside my box to something that makes sense to them.

This is much like getting in someone's car and changing the radio to what you want to listen to. Without asking. And even if you asked, they really couldn't say no.

Of course, some of this may seem hypocritical, because I have no problem with trying to get you to alter your boxes. But there's a remove between you, dear reader, and the boss that holds the reins to my paycheck and career. You can take it or leave it, as you please - the dynamics of boss and bossee leave that option out.

There's a very delicate balance that happens here, one which I think Andre treads very carefully. His recommendation gets the boss to use some of the methods you use without giving them her privy to other parts of the box. That's critical.

I'm at the point where I'm really unsure whether it's worth the time and potential side effects to try to get the bosses on board. But I'm curious as to where you all are at on this one.

What do you all think? For those of you who have tried to change your boss' system, how has it worked? What are the best practices? Any unintended consequences, good or ill?

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