Dissecting the Two-Handed Lawyer: Thinking Versus Action in Business Lawyering

Abstract

Business clients sometimes refer derogatorily to their 'two-handed' lawyers, implicitly distinguishing between the thinking that leads up to a decision and the decision itself. A 'two-handed lawyer' is one who can analyze a problem on one hand and on the other hand, but tosses the actual decision back to the client. The observation invokes something fundamental about objective information, subjective judgment making, and the commitment to action. 'Thinking like a lawyer' is a prototype of the rationally analytical mindset residing at one end of the mental continuum, and the entrepreneur’s impatience with allocating the risk of failure is a prototype of the commitment to action residing at the opposite end. If leaping is the metaphor for the business decision, then the systematic and dispassionate 'two-handed' assimilation of data through rational analysis – the lawyer’s stock in trade – plays a crucial role. The leaper uses that analysis to assess distances and capabilities. But the decision to leap is something quite different. The leaper’s subjective experience of the “aha” moment of a business decision (or any decision, even when made by lawyers) defies scientific reduction. It is really only accessible through the subjective lived experience of the decision-maker. Deciding is more like action than thought. In his iconic The Reflective Practitioner, the late Donald Schon criticized a mode of thinking he called Technical Rationality. Prototypical legal analysis is an exemplar of Schon’s Technical Rationality, applied methodically and systematically as a means of helping others to understand their circumstances and to optimize their positions in light of risk and uncertainty. Prototypical entrepreneurs and investors, however, are obliged to decide and to act. The mental process that leads to action is deeply subjective, personal, intuitive, and often ad hoc. Understanding that in difficult cases it is possible to offer as many reasons for as against the proposed action, the most effective business lawyers do not merely analyze and offer 'two-handed' alternatives. Instead, they put themselves in the position of the decider and understand what it means to take the leap of a business decision. This article is a reflection on the reasons for lawyerly 'two-handedness' and some preliminary thoughts on overcoming it. The affective toolkit for getting beyond rational analysis to action includes attributes such as epistemic humility, epistemic courage, self-awareness, and the willingness to accept responsibility for the consequences of one’s decisions. The practical toolkit will follow in another essay.