First, focus on slowing down and remembering that you’re talking to a person, even if that person happens to be your boss or boss’s boss. This sounds silly, but we all forget to do it. Here is a story: A couple months after joining Google, I disagreed with Larry Page about his approach to an AdSense policy. I wrote an email to several colleagues, which said, “Larry claims he wants to organize the world’s information, but his policy is creating clutter sites, muddling the world’s information.” I went on to imply that his policy was focused on increasing Google’s revenue rather than doing the right thing for users. (Nothing could have been further from the truth. I just didn’t understand what Larry was trying to achieve because, not surprisingly, he was about 15 steps ahead of me.)
If Larry had worked for me instead of co-founding the economic powerhouse of our century, I would never in a million years have sent such an arrogant, accusatory email. I would have asked him privately why he was proposing the policy when the results seemed to be in violation of Google’s mission. If I agreed with his rationale, that would have been that. If I disagreed, I would have explained, again privately, that he seemed inconsistent, and tried to understand his point of view. I didn’t do any of that.
Why did I behave this way? Partly because I believe there’s a special place in hell for those who “kick down and kiss up.” At least I wasn’t making that mistake. But the main reason was that I didn’t really think of Larry as a human being. I saw him as a kind of demigod whom I could attack with impunity. Just because there’s nothing more despicable than “kissing up” and “kicking down” doesn’t mean the opposite is admirable. This is so obvious that I feel ridiculous writing it. I’m sharing it here, though, because I hope that reading this story will help you avoid my mistake.
The clutter sites incident with Larry is a good example of how even well-intentioned criticism can be obnoxiously aggressive if you don’t think of the person you’re criticizing as fully human. The first problem with my email was that it wasn’t humble. I had just joined the company, and I didn’t understand much about how Google’s systems worked. Nor had I bothered to ask any questions about why Larry might be taking the stance he was taking. Instead, I just made a bunch of assumptions and concluded (wrongly, as it turned out) that Larry was more concerned with making money than he was with Google’s mission. Furthermore, my suggestion for how to address the policy issue was not helpful at all because I didn’t really understand the problem that Larry was trying to solve. My other miscalculation was criticizing Larry in a public forum, rather than in private, which would have been the respectful thing to do. And I personalized. I impugned his character by accusing him of hypocrisy. Lesson learned!
So, remember you are talking to a person. Find something about that person that is interesting to you. There are people in your life you care about. Apply what you know about those personal relationships to your work relationships. Work relationships are not friendships, but they are still relationships. When you’re challenging somebody who knows you care, that person will likely take your criticism in the “right way,” even if you say it the “wrong way.” Be “kind,” but don’t just try to to be “nice.” The problem with all the “how to say it nicely” advice out there is that it can make you sound insincere. If you say it “nicely,” but don’t genuinely give a damn about the person, they’ll see through you every time. You’ll look and feel like you’re kissing ass...Another thing you can do is to be open to criticism yourself. Remember, you may not have full context, and you may be wrong.
Also, here is some more about what I mean by radical candor being HIP (Humble, Helpful, Immediate, In person, Private criticism / Public praise, do not Personalize). What follows are some additional thoughts on what that means. But, please don’t let the additional thoughts or the acronym paralyze you. Whatever you do, don’t sit there saying nothing trying to remember what I stands for. For the vast majority of people, the really important thing is to just say what you think.