To work well with anyone you need to be able to criticize him or her.
But you’re a nice guy, you want to give everyone the benefit of the doubt and you don’t want to hurt anyone’s feelings. How do you go about criticizing them?
Before diving into how to criticize, the first thing to remember is to know when to. It’s a fine line. If you don’t criticize enough, you’re not pointing out critical problems that need to be solved and helping solve them; if you criticize too much, you’re the asshole no one likes.
The two rules of thumb I try to keep in mind are: first, if it is actually an important issue—or even a metaphor for an important issue—then mention it. Just make sure you get to the deeper issue that underlies the criticism. Go into the deep end of the pool, or don’t go into the pool at all.
The second rule of thumb is to make sure you say 10 positive things for every one critical thing. We can quibble about whether the ratio is 7, 10, or 20 to 1—but it’s definitely something in that ballpark. If you say 2 nice things for every one critical thing, you’ll quickly become the despised @#$(*&. And that’s not good unless it’s part of your strategy to be that person.
So now, let’s say these criteria are passed and you need to give someone some criticism. Here are a few ways to make it easier:
First, only say something behind someone’s back if you also say it to their face. If you don’t say it to their face directly, you’re a conniving @#$(*& again. This is a rule of thumb I try to follow with an iron fist and personally never make any exceptions to it. None.
Second, I make sure I always articulate what is happening from the other person’s point of view, in a way that assumes he’s a good person. Why is he making the mistake? “John just can’t code in a professional setting. I think it’s because he’s a creative spirit and deadlines, deliverables, and daily meetings are something he can’t motivate himself to do because he just wants to be an artist, and the code is his art.” Framing the other person’s thoughts so they look good also separates you being an @$#&^* from being the good guy trying to help.
Third, I’m not someone who gives criticism naturally. Or at least that was the personality I grew up with. Here’s how I grew into it when I internalized and realized the above points on how important it is: I pretended I was an actor. You know savvy, blunt-talking New Yawker who says what he’s thinking? I’m not that person but I pretended to be. And a magical fact about life is: if you act a certain way, for enough time, it becomes a part of you. It becomes you.
