Try these techniques to crack the code and learn what your boss really thinks:
Follow the paper trail. Some bosses don’t like to talk much, but they reveal more in their writing. Keep a file of the boss’s memos, reports or other correspondence. Inspect the writing style. How does she draw conclusions or align facts to form an argument? Does she favor certain kinds of imagery or is she bare-bones direct? The answers can help you figure out how to communicate with her for the best results.
Drive discussions with silence. If you’re dealing with a “silent clam,” you may fall into the trap of talking more when you’re in the boss’s presence as a way to relieve your anxiety and keep the conversation rolling. But that only serves to make the boss more inscrutable. Try playing along with a quiet boss by spending time in his company not saying a word. When you’re in the midst of a discussion and neither party is talking, make sure he’s the one who fills the silence. He probably isn’t used to people showing such comfort in silence, and he may open up to you in time.
Separate your self-image from what the boss thinks. In the absence of clear feedback from your boss, you may start drawing alarming conclusions that you’re somehow failing or losing your ability. Realize that your boss’s personality quirks have nothing to do with your performance. Example: Your boss asks you for a market analysis. You provide it the next day as requested, and he never gets back to you. Rather than wonder, “Did I turn in faulty work?” move on and don’t expect your boss to acknowledge your efforts.
Spend time with the boss in an informal setting. Even if she’s unfriendly or just plain awkward, arrange to accompany her on a company outing, or try to sit together at a community event. Don’t hang around like a pest, but be receptive to casual conversation. Sometimes people act differently outside the office, and you can get to know them better.
Ask comparative questions. An inarticulate or mysterious boss may not say much, but at least you can gauge his opinions by asking him to compare two elements. Examples: “Between the new brochure and print ad, which did you like better?” or “Did you find either of the two proposals worth a second look?”