Jeffrey Beir isn’t your average CEO. Rather than work his way up the corporate ladder, he abandoned an executive post at Lotus Development four years ago to cofound eRoom Technology, a company that creates virtual workplaces on the Web. Like many entrepreneurs, he soon found himself running a growing business and wrestling with a load of new challenges. Though he had solid skills in technology and marketing, he faced many questions that lay outside the range of his experience: Which headhunter should he use to bring in new managers? How should he develop a strategy for allocating funds? What’s the best way to work with a board of directors?

A version of this article appeared in the September–October 2000 issue of Harvard Business Review.