Building Sound Judgment into the Art of Leadership

“Turn him to any cause of policy, the Gordian knot of it he will unloose, familiar at his garter” 

–Shakespeare, Henry V

Leaders, do you train your team how to make good decisions? If so, how do you do it? When, as part of a leader’s development, do they learn the art of judgment? What constitutes good judgment? What are the means by which a young leader acquires the range of skills, abilities, and character to become proficient in this area?

The most important decisions that leaders make are fraught with complexity and ambiguity. They cannot be reduced to policies, analysis, and formulas. However, in the absence of sound judgment, that is exactly what happens. Tim Keller, in reference to the Pharisees, said, “Specific rules are always easier to obey than broad principles. By creating a hundred minor procedures, it becomes possible to feel you have fully complied and to feel righteous for doing so.” 

How then do we sort through all the variables to ensure the very best outcomes without defaulting to mindless prescription? What are the constituent parts of a particular issue or decision? How does one forecast the outcomes of the possible solutions being considered? Are you taking input from the right sources? Are you able to intuit the salient features of the situation? What are the values that shape your decision hermeneutic? What baggage are you bringing to the table? What are you possibly leaving out?

Enter Phil Mickelson (seriously, hang with me a second). See the clip below – it’s incredible. What it reflects is a level of internalized mastery that is only acquired through deep knowledge, practice, habituation, and skill. Mickelson, as it pertains to his golfing abilities, has what Josef Pieper calls, solertia (quick-wittedness, acumen). He can explain all of the minute details of his craft, the why and how, but he doesn’t do that in real-time. He intuitively assesses the variables in front of him, and he decides his course of action accordingly. Lewis says you are not dancing if you are still counting steps. There is beauty and fluidity in the embodiment of virtue. It is an excellence worthy of emulation.

I don’t think we ponder making decisions like this. Or, if we do, it is certainly not reflected in the way we typically train leaders. To cultivate wise leaders and master prudent judgment, we must reclaim a vision of leadership that not only strives for excellence but instills the practices of virtue.

Phil Mickelson – A great example of the chunking process, Golf’s Mental Game

Society for Classical Learning

At Society for Classical Learning, we believe that cultivating sound judgment and leadership rooted in virtue is essential for shaping the next generation of classical educators and leaders. Our community is dedicated to fostering these principles through collaborative learning, professional development, and shared wisdom. If you’re passionate about shaping thoughtful, principled leaders, consider becoming a member of Society for Classical Learning today. Join us in building a future guided by wisdom and integrity.