3. Pick your battles
Sometimes, no matter how brilliant an idea might be, you're just not going to get legal approval. Assuming that you're not obviously violating any laws, much of this comes down to your company and legal department's risk tolerance level. Focusing on the education of your legal team will eliminate some of the uneducated "no" answers, but sometimes you'll still need to fight your point.
Common sense plays a big role in many cases. Unfounded "no" responses from your legal team can simply be a case of overzealous CYA behavior. In the legal world, this behavior may make more sense, but from a marketing standpoint it can seem completely absurd.
As an example, around a year ago, I needed to get approval from the legal department of a major insurance company for a print ad. We were using this company's rate chart, which is the only reason their approval was required. They didn't object to any of the words in the ad copy but took issue with the font size and color of the word "Urgent" in the headline. The explanation for their decision was the type of thing that could easily have been featured on "The Daily Show" for its hilarity and absurdity.
In this case, it was obvious that we needed to fight to get approval. After a discussion with a high-level executive at the insurance company as well as the head of the legal department, we finally got the sign-off on the ad that we were looking for without having to modify it in any way. This was a case where plain common sense trumped any legal explanation that could possibly be created.
On the other hand, there are some cases where you're just not going to win the battle no matter how well you educate your legal team or plead your case with a well thought-out argument. Most of these battles are going to depend on the risk tolerance of your company, your legal department's interpretation of "gray areas" and the alignment of your legal department with your company's business goals.
