What you know the most about is what you can offer the most insight about. And you probably know that telling stories is always more compelling than talking in generalities. But if you tell stories, you need people to be in the stories. So if you want to write insightfully, then using stories about people close to you makes sense.
Writing about a co-worker is similar to writing about a sex partner: you know a lot about the person, both good and bad. So you could ruin your relationship by writing about them. So you have to get good at writing about co-workers without pissing them off.
Negotiate before you write
Readers always complain that I'm ruining my relationships by blogging about them. (The record-breaker number of these complaints is on this post about my ex-husband.) But I know a bit about this terrain: I sold a novel in my 20s that included all my sex partners. And in graduate school for creative writing, I wrote my master's thesis on my sex life, in real time. (Stop Googling: It's under a pen name. Remember? I’m the queen of pen names.)
Anyway, from that experience, and from writing a column about my workplace for three years in the 90s, I have a lot of practice negotiating with people before I write about them.
With a boyfriend, or a close co-worker, I explain to them that they will always have veto rights, so they don’t have to worry about what they do or say with me. They are always surprised, and they are always relieved.
The truth is that any writing is just one person's very skewed version of the story. So what they read about themselves is always jarring at first, and then the person ends up not minding. I have found this to be true in most cases.
Also, once you know you’re negotiating, then you have more latitude. Sometimes people will say, “Don’t write this,” before they tell me something. I always say okay. Because of course I want to know what comes next. And I can negotiate later if it is interesting enough to write about.
Let people edit what you write about them
You must write it all out first before you show them anything. They will feel out of control at first when they realize it's not their version of the story. But they feel more control when you tell them to edit. Usually, the person does not change anything. Or they ask me for one, tiny adjustment.
For example, in the post where I am screaming at the 25 year old for not going down on me, he asked me to change “and you don't know how to do oral sex” to “you don't do oral sex,” because, he reasoned, how could I know?
Know what can't be said
My brother works at Microsoft. Everything is off limits unless he's forwarding me a press release. Another brother of mine worked at McKinsey, and he'd have great dirt on the higher-ups of the world, but everything was off limits.
Dissing where I live — Madison, WI — gets me in trouble. Not that I don't do it. I do. For example, the public schools here stink. And I refer people to national rankings, and people tell me the rankings don't matter. But really, public schools are a function of money. Madison is not a city bathed in wealth. This should not be controversial. But apparently it is.
So I'll hide it in a post about blogging, which few Madison people will read. They mostly read the sex stuff, I think.
Anyway, you'll find quirky, sensitive spots that each person has. Stay away from those. Even if you know you have great insight.
It's not a function of age or experience. It's a function of self-confidence and personality type. Very sensitive people are tough to write about because they will take anything you write much too personally.
So, the higher up in the organization someone is, the more likely they will be okay with you writing about them.
Part of that is self-confidence. It takes a lot of self-confidence to get to the top of anything. And part of this is being comfortable with oneself. People at the top usually know where their weaknesses are and they can laugh at themselves. Also, they have perspective, because they're putting out fires each week. And they know your blog is not a real fire.
Remember that people exaggerate their own importance
Unlike Ryan Healy, another of my co-workers, Ryan Paugh, does actually care what people think of him. (Which might be the biggest difference between the two of them.) So I waited longer to put Ryan Paugh in the blog. But when I did, it was about a rash in his groin.
I showed it to him beforehand, of course. And he said, “Why'd you have to put that in?”
“Because it's funny.”
At that point, Ryan Paugh had learned enough to know that other people don't care. They might care for a second and then they forget about it.
But most people don't understand this. Most people think every detail of their life is really scintillating, and everyone is analyzing every word about them. Write about people who get it.
Don't blog anonymously.
I wrote anonymously for three years. I was doing startups, and writing on the side, and had no idea how big my column was. I knew they had moved it from online to print, but the pay was so bad, relative to software startups in the dotcom 90s that I had no idea I was writing a big column.
I also had no idea that my whole company was subscribing. People thought it might be me, because of a column I wrote about going to the E3 conference. But I really gave myself away with a column that announced our CEO was bi-polar and a column that documented my boss sexually harassing me.
Blogging anonymously is bad for a lot of reasons, but especially because it is a way to not be careful. If you are anonymous, you will not follow any of these rules. Because blogging is work, and following these rules is more work. But you eventually will be found out. It's how the world works. I mean, if your blog is at all successful, you'll be found out, and if your blog sucks, why are you doing it anyway? If you are not anonymous, you will always be careful.
Surround yourself with people you like.
You will never hear me hating a co-worker I'm writing about. It's too dangerous. I could end up being too mean for public consumption. I could end up telling him stuff he didn't already know. You don't have as much control over what you're writing if you write about a co-worker you hate. So I only write about hating non-coworkers.
For example, I rip on Ryan Healy all the time. We are always fighting. But I adore him. I feel lucky to work with him, and one of the reasons I'm lucky is that he lets me write about him. Whatever I want.
This is true of boyfriends, too. I don't date men who suck, so I am able to write about them in ways they like. Usually, if I can make them laugh they'll let me write anything. So maybe the best advice I have for you when it comes to blogging about co-workers is to leave them laughing.