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Cross-selling, like cross-dressing, is a tricky business. Style matters first; ultimately so does substance, but not at first blush. Asking for new business from an existing client — cross-selling new services — is one of the most profitable ways to gain new revenues because it is easy on profit margins; it takes little time, the client is a known quantity, so you know how to work with him or her, and your reputation precedes you.

Many firms recognize that litigators, especially, are not successful cross-sellers of transactional services, because they have been trained in the school of “Never ask a question to which you do not know the answer.” Transactional lawyers, too, often struggle with cross-selling because they forget to mention all that they or their partners do. The cross-selling hunt, however, turns on asking the right open questions in specific ways to pave the way toward a larger working relationship. Specifically, the more surprising the answer, the greater its rainmaking value.

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