On strategists and strategy : collected essays, 2014-2024

I recently found myself fascinated with Lawrence Freedman’s work On strategists and strategy, specifically his essay titled "Strategy’s Evangelist," which reflects on the profound legacy of the late Colin Gray. Gray, whom Freedman describes as a tireless advocate for the importance of sound strategic thinking, provided a maxim that is helpful for the modern legal practitioner: “Strategy is ever varying in character, but not in its nature, which is unchanging” (p. 150).

As we witness a massive shift in the character of law, largely driven by generative AI, it is easy to mistake these tools for a revolution in the legal profession itself. However, Freedman helps remind us that the nature of legal strategy remains exactly what it was a century ago. Just as Gray argued that the core issues of conflict (like balance of forces, morale, and terrain) remain recognizable across history despite new weaponry, the fundamental legal tasks of allocating risk, defining leverage, and securing performance are similarly timeless. We must remember that there are no truly "new" ideas in strategy, but rather a "stock of concepts of great antiquity" that must be perpetually applied to the present (p. 151).

The nature of any legal deal is fundamentally human. Strategy, as Gray defined it, is “the bridge” that relates specific means to a larger purpose (p. 153-154). In our context, that bridge is built on trust, leverage, and consequences. Effective strategy requires the ability to influence the “minds and actions” of others, a task that remains a struggle against severe odds (p. 159). While a digital tool can process data, it cannot navigate the psychological nuances of a high-stakes negotiation or the intangible weight of a reputational risk.

Gray reminds us to not let the "character" of modern tools automate our strategy (p. 154). We can, and should, automate the tactics; the drafting of templates, the searching of databases, and the routine military-like behavior of "engagements". But we cannot automate the "bridge" of judgment. As Gray noted, while a strategic framework can help order one’s thoughts, it “cannot generate the actual thoughts” (p. 154). Tactics without strategy achieve nothing.

The role of the strategist is, as Gray suggested, "heroic" precisely because it requires extraordinary natural gifts, nurtured by education and experience, to see the "big picture" and stitch together performance at every level (p.159). As we integrate new technologies, our vocation remains the same: to be the educated strategist who can be trusted to develop the doctrine that staples together various efforts into a synergistic whole. We must keep our eyes fixed on the eternal truths of conflict and cooperation, for while the tools of the character may change, the nature of our strategic responsibility is permanent. 

On strategists and strategy : collected essays, 2014-2024 Freedman, Lawrence,  2025, Book , 336 pages; 0197814654, 9780197814659