‘The Chess Players’ by Thomas Eakins depicts two men engaged in an intense game of chess. While a third person stands between them and looks pensively at the board.
This painting captures more than just a game of chess. It's about perspective, strategy, and understanding roles. It represents the idea of seeing the whole board. A notion often linked with being a strategic advisor who can anticipate future moves.
Recently, I had a conversation with a former military member from the 82nd Airborne Division, a division I once served in. He sought advice about setting up trusts and various complex structures for a business he hadn't even started. He was receiving advice as if his advisors were overseeing a chessboard, dictating complex strategies for situations that hadn’t even arisen yet. Again, all accurate advice. All things that I agree with. And all things that I get paid to do. And I told him you should not be doing any of that—because the advice was impractical for the context. He hadn’t even started the chess game. “You only have one job right now. Make money. All this other stuff is irrelevant.”
This interaction underscores a critical misunderstanding in strategy. We portray the strategist as someone who has planned every move in advance. But true strategy involves adapting to what's directly in front of you. This is where understanding roles becomes crucial. There’s a doer and a thinker, a player and an observer, an actor and a writer.
In business, you are often both the player and the observer. You’re at the table, deeply involved. You might think you’re stepping back, observing the whole board, but usually, you're not; you're right there in the thick of it. This is something vital I learned from Shakespeare's approach to his plays. He wrote the scripts, yes, but he didn’t tell the actors how to interpret each line.
Similarly, in the business world, while you are playing the game, you need an advisor who truly stands back, unswayed by the heat of the moment. This advisor isn’t there to play the game for you or to predict every future move. Their job is to look at the facts, understand the rules, and guide you based on what’s happening now.
Much like the Sword of Damocles—when you're sitting in the chair you have a different perspective. And that's the perspective that matters. It’s just incomplete.
It is a myth of the median that you can simultaneously sit in the chair and look at the board. And it is brash overconfidence for an advisor, standing above player and looking at the board, to think they can direct the game.
I liken this role to that of a wise court judge, who listens and observes without getting drawn into the politics or the drama. Judges focus on the facts, applying the law dispassionately. They aren’t playing a political game; they’re interpreting the rules as they see them. My job is not to play the game. It's to just look down at the board and talk about the facts that are on the board.
This painting is not about my opinion with respect to being a True Advisor. It isn’t about strategic superiority or seeing all the moves ahead. It's about understanding the roles each person plays and the mutually profitable relationship the parties have to each other when they respect those roles.
It’s about understanding where you are right now, helping you navigate immediate challenges, and preparing for your next moves. The purest achievement is to increase the probability of positive outcomes and decrease the probability of negative ones. As no move is ever made with complete certainty.
“Never let any Government imagine that it can choose perfectly safe courses; rather let it expect to have to take very doubtful ones, because it is found in ordinary affairs that one never seeks to avoid one trouble without running into another; but prudence consists in knowing how to distinguish the character of troubles, and for choice to take the lesser evil.”
– Machiavelli
I cite Machiavelli as his counsel was prudent to rulers of Nations. The parallels to business are obvious.
This is the art of advisory—not standing above from a position of superiority, but standing back to give a clear, unbiased perspective.