I just got back from a presentation by Robin Goldsmith on How Managers Get So Stupid held by the Software Quality Group of New England, which I thought made a rather interesting point about… well, the rest of us.

Imagine the boss walks up to you and says, "I want you to build me a super-dooper-twitter-style-ajax-enabled-application-to-allow-regular-folks-to-bring-about-world-peace-through-social-bookmarking that we can promote at the Aren’t We Cool conference this August."

Well, right away BIG, FLASHING red lights, buzzers, and all sorts of other warnings start going off in your brain. What in the world is this guy thinking? That’s only 2 months away, no one on the team has any experience with Ajax, and even if they did, every last developer is already tied up through the end of the year on other "top priority" projects.

Oh, and, by the way, solving world peace with twitter??

So, okay, even if you are a truly eloquent haxor, what comes out of your mouth at this point is probably going to be a lot more about what we can’t do then what actually might be possible. And even if you do try to talk about what’s possible you’ve probably already flipped the bozo bit on this guy, and that kind of condescension tends to come through pretty loud and clear to the person you’re talking to, regardless of how well intentioned you might be.

Just for a moment, put yourself on the other side of this conversation and think back to a time when you had an idea that you really wanted to see happen, but the first person you present it to totally misunderstands you and says, "what are you, STUPID? Of course that could never work!"

Okay, so maybe the guy actually understood you pretty well, but knew something that you didn’t. Regardless, do you really think you’re going to stand there and listen to this guy — who’s calling you an idiot — to give him a chance to prove his point? Not likely. You’ll probably write him off as an annoying nay-sayer and do your own thing anyway.

Which, unfortunately, tends to be exactly what managers do to us when we respond this way. Rather than recognizing that we’re actually speaking from experience and trying to protect them from failure, they flip the bozo bit on us and just proceed exactly as they originally intended.

Voila, stupid managers, just add water.

Robin’s point is that we can help things along by being a little more thoughtful in our messaging. Instead of focusing on what can’t work, actually stop for a moment and try to think up some options that might work. And then, share those ideas, and educate the manager a little – give him some options that would be feasible so that he can figure out where he wants to take his idea. If we just say "well, you can only have a single, static web page and nothing else!" – that’s an option, alright, but it isn’t really improving the situation.

If instead, you do a little listening to understand what he wants, a little educating to help him get a feel for reality, and throw some options out, now you really are helping him, because you’re giving him the information and the options he needs to figure out how to make his idea work in a non-stupid kind of way.