When Aruba Networks was considering a sale of the wireless-networking company to Hewlett-Packard in 2014, the board of directors turned to an investment banker who made his name during the last technology boom.

Frank Quattrone worked for four and a half months trying to nail down a deal. But then there was a problem. Hewlett-Packard chief executive Meg Whitman refused to negotiate with Quattrone because he had been so difficult to deal with in previous deals, says someone close to Whitman.