The answer to this question is largely dependent on other variables. All other things being equal, the person with the higher degree is likely to perform in such positions better. (I am assuming we are speaking about a master's or higher in business.) However, a person with more experience in management, without the higher degree, could very well perform more ably than the person with no experience, but with the higher degree. Another factor that could come into play is the person who has experience in a particular industry. For example, if I were looking to fill this position in the automotive industry, I might be more likely to hire someone with only a bachelor's degree who had a few years experience in that particular industry, as opposed to someone with a master's who had no experience in that industry. Still another factor is the quality of the school attended. A master's from a state school might be less impressive than a bachelor's from an ivy league school. In choosing someone for an upper management position, it is the combination of education, skills, experience, and personality that matters.