Have you ever noticed that some (maybe most) lawyers tend to have a “glass half empty” view of the world? What I mean is, they look at challenges as road blocks that can’t be circumnavigated and immediately jump to the conclusion that the deal can’t be done. They even speak that way in initial meetings regarding a project or transaction, informing the client that the desired outcome is not achievable – often before they’ve even gathered the necessary information to fully understand what the overall goal/objective is and how the proposed deal will help reach or further that goal/objective.
In my opinion, businesses don’t (or shouldn’t) hire lawyers to merely identify problems or tell them what they can’t do. If that were the case, they’d be better off saving the legal fees. Rather, we’re hired for the purpose of, and we should view our primary role as, (a) first, fully understanding the desired business objectives, and then (b) finding a way to achieve them, even (especially) when that way is not easy or obvious. Furthermore, a lawyer should be constantly thinking and advising the client as to how the deal could be even better from a business/legal standpoint – whether that means restructuring to achieve a more favorable tax outcome; eliminating, reducing or shifting risk; reducing costs or administrative burdens; avoiding unnecessary complexity; or minimizing uncertainty.
Certainly, there will be times when the best service a lawyer can provide is to advise a client that a deal cannot or should not be concluded or structured in a given way (or at all) due to legal constraints. However, even then, in almost all cases there’s still a work-around or alternative strategy that’s at least worth considering to accomplish some of the client’s goals.
Most lawyers are, by their nature, cautious, conservative, skeptical and critical. Business people, however, make money by taking (calculated) risks and closing deals. Their lawyers need to understand this and provide advice with the same “can-do” attitude that has allowed their clients to succeed.