One of the most challenging decisions a company can confront is whether to diversify. The rewards and risks are extraordinary. Success stories such as General Electric, Disney, and 3M abound, but so do stories of failure-consider Quaker Oats' entry into the fruit juice business with Snapple. What makes diversification such an unpredictable, high-stakes game? First, companies usually face the decision in an atmosphere that is not conducive to thoughtful deliberation. For example, an attractive company comes into play, and a competitor is interested in buying it. Or the board of directors urges expanding into new markets. Suddenly, senior managers must synthesize mountains of data under intense time pressure. To complicate matters, diversification as a corporate strategy regularly goes in and out of vogue. In short, there is little conventional wisdom to guide managers as they consider a move that could greatly increase shareholder value or seriously damage it. But diversification doesn't need to be quite such a roll of the dice, argues the author. His research suggests that if managers consider six questions, they can reduce the gamble of diversification. Answering the questions will not lead to an easy go-no-go decision, but by helping managers weigh risks and opportunities, it can help them assess the likelihood of success. The issues that the questions raise, and the discussion they provoke, are meant to be coupled with the detailed financial analysis usually conducted before a diversification decision is made. Together, these tools can turn a complex and often pressured decision into a more structured and well-reasoned one.