Asking, Guessing and Leadership

I don't remember who it was that first told me this, but somewhere along the way when I was growing up someone gave me some pretty powerful advice. They said, "If you want something, ask for it. After all, what's the worst that can happen? They just say no. You're no worse off than you were before you asked."

So, right now, many of you are thinking, "Yeah, that makes sense." And, there are also a lot of you who are thinking, "That's a really rude and pushy approach to life."

That, in a nutshell, sums up the point of an interesting column that Oliver Burkeman wrote for the Guardian recently. His core question is are you asker or a guesser? Askers ask directly for what they want. Guessers only make a request when they're pretty sure they're going to get it. As Burkeman points out, the awkward and weird moments come when Askers and Guessers mix. (Which, of course, happens all the time in real life. That's why real life can be so awkward.) Askers will usually settle for a clear no and move on. Guessers often have problems giving a clear no. Awkwardness and hilarity ensue.

So, since this is a blog about leadership, how do you think the Asker and Guesser profiles affect the practice of leadership? Is one approach better than another for leaders? What have you learned about dealing with Askers? What about dealing with Guessers? Which one are you and is that working for you?