Ever since AI became the beginning, the middle, and the end of every conversation, everyone wants to talk about judgement and critical thinking. Business leaders want to make sure their employees will have it and wield it, and HR departments want to know how to develop it in their employees.
That’s all good and fine, but there’s more to it than rolling out a quick online training program. I offer four key ideas, which hang together as an integrated and self-reinforcing system. Each is synthesized briefly for the sake of readability, but brief outlines cannot possibly do justice to such important concepts, so follow-up readings from my blog are offered in case you would like to dig deeper on any of the key ideas.
1- Character underpins reason
While judgement — what the Ancients knew as practical wisdom — is a virtue of reason, it is underpinned by virtues of character such as courage, humility, temperance and many more. If you want to foster sound judgement, you must also attend to the virtues that underpin it. And unfortunately, there is no finish line. It is, and will be, an ongoing effort.
Deep dive: The link between wisdom and character
Will character alone prove sufficient? Unfortunately, not. While character is a necessary condition for wise leadership, it’s not sufficient on its own. Sound judgement in an organization requires both virtuous human agents and well-engineered institutional systems — clear incentives, robust governance, and disciplined decision protocols all working together effectively. The finest character will struggle within a broken system, just as the most sophisticated system will fail without people of integrity to navigate it. But wise people will design a better system than unwise ones, which brings us back to the key thesis.
Deep dive: How high-stakes decisions change who you are
2- Broad knowledge over deep silos
Judgement requires broad and sound knowledge. You can’t reflect in a vacuum, so both general and specific knowledge have to be cultivated, and not just a little of both. The broader your knowledge, the more perspectives, analogies and frames of reference you can bring to bear on a difficult problem. Good judgement depends in part on having a sufficiently deep well of knowledge from which to reason.
Deep dive: Leadership and general knowledge
3- Sound judgement is a social endeavor
As Owen Flanagan wrote: “The claim that reason is powerful is not a claim about the reason of singleton agents deciding momentous events by themselves, moral Robinson Crusoes. Reasoning is social and historical, something we do with others, and with the resources of human history and culture.” (Flanagan, 2017, p. 20) To foster effective decision-making in your organization, you’ll require the power of diverse and wise (enough) people deliberating together effectively, which is one of the most overlooked benefits of effective teamwork (no, the unending parade of PowerPoint decks at your weekly management meetings doesn’t count).
Deep dive: The challenging project of being a good team
4- Autonomy sustains maturity
You can’t desire the benefits of good judgement from your employees while at the same time undermining the autonomy and agency that sustains it. If you want your employees to show up with the maturity on which sound judgement is predicated, you have to build the kind of culture that encourages this kind of maturity.
Deep dive: Fostering organized maturity in the workplace
Seen this way, an organization’s capacity for good judgement is an emergent property of a complex human system rather than a discrete skill that can simply be taught. Character, knowledge, autonomy, and effective deliberation all interact and reinforce one another through experience over time. Building such a system may feel painfully slow at first, but individual and collective wisdom accumulate through practice, and so do the benefits.
None of this is about over-moralizing every operational call, by the way. Many decisions, for instance, are rightly grounded in technical rigor and nothing more. But people endowed with good, ethical judgement will more readily realize when a matter crosses, in this example, from the technical to the ethical and other decision-making resources have to be mustered. Perhaps, if their organization aligns more than less of the conditions outlined above, the decision that comes out of the deliberations will be deemed genuinely good on the dimensions that matter most.
And perhaps, if you have invested over time in the conditions that support good decisions, you may also be surprised to find that your decision-making is not only good but also faster and more decisive. Practice makes better, after all, and people experienced at making good decisions will generally do better at this than people who aren’t, while preventing the kind of downstream grief (including unproductive rework) that often stems from poor initial decisions.
Building sound individual and collective judgement takes systemic investment rather than quick fixes. How is your own organization supporting the development of good judgement and critical thinking?
References
Flanagan, Owen. The Geography of Morals: Varieties of Moral Possibility. Oxford University Press, 2017, 362 pages.
