People you know and people you don't know don't want to hear what's the matter with them. Especially from you. Sorry, but that's just how it is. It's not that they don't appreciate your wisdom and keen insight. They do! But they have other things to worry about at the moment. Think back. Did it ever work in the past? Has anyone in recent memory told you, "Thanks for pointing out what a jerk I am! I'm so pleased you spoke up!"? Probably not.
Co-workers, friends, family members and casual acquaintances, specifically, have long memories when it comes to you saying negative things about them. You know this - why deny it? You are free to deny any gossip or slander that's been attributed to your name, naturally. But when you tell someone straight out what you think their problem is, even in that delightful, well-intentioned way you have, your cover is blown. Game over.
Here's the crazy part: People want you to figure out how they see themselves -- on a good day -- and confirm it for them. Period. It's also essential that you approve. They hope that you'll notice and validate their unique identity, and buy into the image they have, or would like to have, of themselves as heroes in their own stories. (Don't laugh. You want it, too.)
Continue to validate someone's fondest self-image -- punch that ticket for 'em -- and they'll be your ally for life. Doesn't that amount to cheap flattery? No, most emphatically not...unless you're faking. Which I don't recommend, because you'll eventually get caught. Insincerity is much more difficult than it sounds; doing it well takes years of dedicated practice.
Oh, but now you say, "Mr. Mark Jaffe of mysterious origin and sketchy locale, you are clearly one confused dude! Didn't you just recommend in a column on telling your boss the truth that an employee builds credibility and trust by saying the difficult, unvarnished thing?" Well, you are absolutely right. I did say that. Please keep those cards and letters coming.
First, that only works with a direct or dotted-line superior. If you try pulling it on a peer or a subordinate, or worse, jump levels and go above your boss' head, it'll backfire. Big time. Providing such specialized service at critical moments is a professional courtesy, on par with a fastidious butler who ensures that his master's coat is lint-free. (Think Bruce Wayne's Alfred.) You must stay in character and remain steadfastly loyal. Second, it's not a summary -- ever -- or a general diagnosis of what you think is "wrong" with the person. It's a random flash in time, a mere anecdote. Certainly nothing that defines.
For more on how to deal effectively with the Powerful and the Super Rich, watch this column for previews of my forthcoming book, Less Is More: It Usually Costs Nothing to Say Nothing. (I can neither confirm nor deny that BeyoncÃ© will be appearing at the book release to demonstrate her friendship, admiration and support.)
I would hope it's understood that I'm not advising people to withhold their opinions from each other, particularly at work. Because I love a good fistfight. But it can't be personal. Or prescriptive. Which brings us back to our fundamental rule: It costs nothing to say nothing. Most of the time. So when in doubt, try going with that.