In 1999, the nonprofit Fair Labor Association (FLA) was launched to monitor factories around the world for sweatshop-related infractions. Another key nonprofit player, the Worker Rights Consortium (WRC), was launched in 2000. The two organizations had similar goals, but very different histories, strategies, and ways of operating. One major difference was that the FLA board included corporations, while the WRC board contained no industry representatives, but only representatives from the United Students Against Sweatshops (USAS), member universities, and labor-allied NGOs (non-governmental organizations). Mission-wise, the FLA focused on all apparel, while the WRC only focused on apparel bearing college and university names and logos. The fact that the FLA included company/industry representatives on its policy-making board, and the WRC did not, created not merely a difference but a source of immediate disagreement and conflict. By 2008, the WRC had grown from a membership of 44 colleges and universities at its founding to 174, and the FLA had grown from 100 colleges and universities to 205. Although the two organizations had often been closely associated together, appearing on panels, and even occasionally collaborating, their shared history had been controversial and tumultuous. Among the issues under continuing dispute were the role of third-party labor unions (which were not allowed by the government in countries such as China and Vietnam), the problem of "living wages" (which would raise production costs considerably), allegations voiced on the website "FLA Watch" (which seemed to many to be one-sided and unfair), and the overall impact of the anti-sweatshop movement's efforts (which led some to question how much progress had been made).

On Labor Day 2002, Cocoa Pete's Chocolate Adventures launched its small selection of gourmet chocolates at high-end supermarkets in the San Francisco Bay Area. The company's founder, Pete Slosberg, had carved a niche out of the stagnant chocolate industry, where he thought a start-up could thrive. His strategy was in many ways derived from the strategy for his previous entrepreneurial success: Pete's Brewing Co. (makers of Pete's Wicked Ale). Of significance was Cocoa Pete's determination to substitute its own production facilities with the underutilized equipment of a larger chocolatier. Cocoa Pete's gourmet chocolates were positioned as irreverent and fun to capitalize on the changing American palette, where the more staid gourmet brands seemed inaccessible. Throughout the strategic planning and product execution, Slosberg and Cocoa Pete's CEO Scott Barnum were pushing to change an industry.

In 1997, the American Heart Association (AHA) Western States Affiliate reorganized to increase fundraising revenues for the nonprofit. Rather than having a wide range of fundraising and programmatic duties, all staff now had key fundraising and programmatic activities. Some staff had been dissatisfied with the new scope and reporting structure of their positions. Roman Bowser, the executive vice president and CEO of the affiliate, made several adjustments to the organizational structure to deal with problems that arose with the organization and had other issues to consider in 2002 related to staff and local community volunteers--the lifeblood of the organization. Furthermore, a national AHS task force was recommending a reorganization of the AHA along the same lines that Bowser had used for his Western States Affiliate. Bowser was not certain that the national center and other affiliates could learn and benefit from his model, which he had tailored for a particular staff and geographical territory. He wondered how and if the AHA could leverage his organizational model across disparate communities nationally and what the impact might be on the long-term viability of the AHA.

In June 1998, the senior management team at Dreyer's Grand Ice Cream faced a number of internal and external difficulties that were some of the most challenging problems the company had ever faced. Problems included profitability issues, record-high butterfat prices, aggressive discounting by competitors, higher margin better-for-you segment collapse, severance of Ben & Jerry's distribution contract, and management health issues. Given a mandatory and necessary financial restructuring of the company, the senior management team faced some tough employee issues and needed to make very significant decisions to overcome their difficult times.