The geek in question: Raymond Chen

The job title: Principal Software Design Engineer, and well-known Microsoft blogger.

What are you working on now?
I've been with Microsoft for 17 years, and I'm currently in the Windows Experience Group. We're the people who do the stuff that end users see and interact with. Basically, anything that goes wrong, it looks like we did it.

What have you learned during your time at Microsoft?
There are a couple of "key learnings" — and yes, I have to use air quotes around that phrase. First, you have to understand what you can do, what you can influence, and what you can only observe. If there's not something you can actively do on a project, if it's something you can only influence and observe, then you have to learn to provide your feedback, and then let go and allow other people to fail. This is another one of these weird lessons … you think it could be done better, but it's their responsibility, their puppy.

People don't learn if they never make any mistakes. You have to let people screw up so they can learn and grow. When people hear this advice, they may interpret it as, like, "Everybody is just screwing up all the time, and Raymond's perfectly fine with it." But it's more nuanced than that.

I sent out a tweet on Twitter looking for questions to ask you, and one guy said, "All I can think of are questions you'd ask Chuck Norris, such as 'How are you such a bad ass?'" So, how does it feel to be the Chuck Norris of Microsoft?
It's actually frustrating — Chuck Norris can't actually do all the things people say he can do! When people go around saying, "Raymond can do this!" or "Go ask Raymond!" it's like, no, I can't actually do all that. Sometimes my reputation precedes me and has elevated me to a level at which I don't actually exist.

So do you feel like the Santa Claus of Microsoft?
Yeah, some sort of mythical creature. And eventually somebody's going to peel back the curtain and realize it's just some guy with a microphone.

Oh, so you're the Wizard of Oz of Microsoft?
I'm a big fan of totally scrambled metaphors.

I understand you're a company folk historian. What's your favorite old school story?
This story was told to me by another old-timer, so it's second-hand, but I like it. So, remember that photo -- the Bill Gates Tiger-Beat-style photo? In the background of that photo is a hotel sign. Bill was working late, preparing for an important presentation the following day.

He finally wraps it up at some ridiculous hour, and he doesn't want to drive all the way home just to come back. So he heads on over to the hotel next door and asks for a room. They ask him for a credit card, but he doesn't have one. He's, like, "I work right over there, okay?" And they're, like, "I'm sorry, sir, that's our policy." Bill's like, "okay, fine" and goes back to the office to sleep on the couch in the lobby or something.

Next morning, does his presentation, yay, it's all good. But of course this is Bill Gates in his irascible, highly temperamental era, so he writes an angry letter to the owner of the hotel lambasting them for mistreating a very valuable member of the community. The owner of the hotel, the story goes, calls an emergency all-hands meeting of all of his staff. Calls them in and says, "This is a picture of Bill Gates, he works next door. If he comes in, asks for a room, he gets one. Any questions?"

Selections from your super popular blog were published as a book a couple years back. How's that going?
It's a strange feeling, seeing the numbers coming back from the publisher … I think the first half of 2008, I sold a net of two copies! It's like, "Oh yeah, I can get half a cup of tea." But, the book has been translated into Chinese and Japanese, which means that now my relatives can read it and know just how boring a person I am at work, too.

So, the book might not be a huge success, but the blog still is.
One of the things about working on Windows is that the stuff you're doing will be running on bazillions of computers around the world, which is a tremendous responsibility. You don't want to be the one to screw it up, because if you have a blog, you then get to post a blog entry saying, "Hi, yeah, that was me. I screwed up over here. Woo-hoo! Sorry! Not gonna do that one again. I'll screw up a different way next time!"

Links, please: • Raymond's blog • Raymond’s book (who knows, maybe it’ll sell three copies this year) • Raymond’s column Windows Confidential in TechNet Magazine