How to Send Your Boss an Anonymous Email

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What’s the best way to communicate with your boss? Open, honest, face-to-face conversation, of course.That would seem to fly in the face of Tell Your Boss Anything, a Web site designed expressly for sending anonymous messages. But it’s not really about giving ol’ Scrooge a piece of your mind; rather, the site appears to have constructive motives.
To get started, you enter your own “trusted” email address (more on that in a bit), then your boss’ address. Next, you create a subject line by filling in the blanks: “I feel ____ about ____.”
Within that first blank, you can choose words like happy, frustrated, irritated, confused, and proud. The words that go in the second blank are up to you.
Then you compose your email. When you click Tell my boss, your message gets delivered anonymously. But here’s the thing: Your boss can reply, and that reply will come to your aforementioned email address — all the while keeping your identity private.

The site cautions you to be “polite, respectful, and helpful,” and indeed nothing about Tell Your Boss Anything suggests that it’s aimed at telling a person off. The idea is more to express yourself in a way that you might not feel comfortable doing otherwise.

That could prove valuable if your boss is the type who doesn’t typically welcome open, honest, face-to-face communication. On the flipside, I think most bosses would likely be ticked off by an anonymous email from an employee, even one that was positive. What’s more, there’s always the risk that the boss will somehow “know it was you,” which might land you in hot water.
The real value here is for bosses themselves, who can use Tell Your Boss Anything to invite anonymous feedback from employees. It’s like a digital version of the suggestion box, a way to let the team know they can communicate with you without fear of reprisal.
Personally, I have no use for Tell Your Boss Anything, because my bosses are all awesome, and I have no qualms about telling them to their faces. Or, you know, by way of a blog post.
But what do you think? Would you ever use a service like this, either as a boss or an employee?

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