Leadership: AI, Wonder, and Wisdom
“Wonder is the beginning of wisdom.”
Socrates (in Plato’s Theætetus)
It might seem counter-intuitive, but in this era where Artificial Intelligence (AI) influences almost all aspects of our lives, there is a real chance that some important skills, both hard and soft, could be lost. Of these, soft skills will likely be the most needed. In 2017, research from the Pew Research Center highlighted which skills will become increasingly important this century.
Every day, we hear about cases where individuals have become so dependent on AI that it has gradually started to diminish their skills. Anecdotal reports often appear on X (formerly Twitter), where teachers and university lecturers observe a decline in grades as students rely on AI for their studies. Research from the Stanford University AI Hub for Education highlighted some of these issues after reviewing causal research from around the world. A sample of this is as follows.
“When AI tools perform information retrieval, organization, and initial processing for students, opportunities to develop metacognition may be reduced. Students may have fewer occasions to evaluate source credibility, identify gaps in their understanding, or select appropriate problem-solving strategies if the AI performs these functions for them.”
Fesler, Lily., Martinez, J.P., Agnew, Chris., Loeb, Susanna. (2026). “The Evidence Base on AI in K-12: A 2026 Review,” AI Hub for Education of the SCALE Initiative. Stanford, California: Stanford University. (p17).
If AI has such mixed results in learning environments, it is plausible that similar mixed results would be seen in organizations. Is it possible that the continued use of AI in generating specialized documents might lead to a decline in specialized writing skills?
Consider this scenario. A person is asked to give advice to a leadership team regarding the organization’s Year-to-Date financial performance and to provide projections for the next fiscal year. The person inputs all the data for the year into an AI agent. The AI generates a report on the data and suggests projections for the following year. The person trusts that the AI’s projections are accurate without much questioning. During the meeting, the report is presented. One of the leaders, an accountant, immediately notices mistakes. They ask the obvious question: How did you arrive at these figures? The person can’t answer the question.
This highlights how relying on an AI agent for financial analysis (a hard skill) without much questioning can weaken analytical skills. The deification of AI means we are placing almost absolute faith in something that can only be as accurate as the data available and the instructions given. The decline of skills in financial and critical analysis, known as hard skills, is concerning. Even more concerning is the inability to wonder—both superficially and deeply—and to gain wisdom in the process.
This emergence of AI is quickly highlighting the need for staff skilled in wonder and the pursuit of wisdom, which is more than just knowledge. Wisdom is found in daily life, in the writings of great philosophers like Plato, and in most religious traditions around the world. At a General Audience in 2014, Pope Francis explained wisdom from a human and religious perspective, as seen through this lens.
“1. …But it is not simply human wisdom, which is the fruit of knowledge and experience. In the Bible we are told that Solomon, at the time of his coronation…had asked for the gift of wisdom (cf. 1 Kings 3:9). And wisdom is precisely this: it is the grace of being able to see everything with the eyes of God. It is simply this: it is to see the world, to see situations, circumstances, problems, everything through God’s eyes.”
Pope Francis (2014). General Audience St Peter’s Square (Wednesday, 9 April 2014). Vatican City.
So there are different types of wisdom according to Pope Francis, earthly or human wisdom and spiritual or divine wisdom. Modern Psychology also sees wisdom as something that goes beyond human understanding. ‘Psychology Today’ offers this definition of wisdom and its components.
Wisdom (as defined by Paul Baltes): “expert knowledge in the fundamental pragmatics of life that permits exceptional insight, judgment, and advice about complex and uncertain matters”…wisdom “encompasses five key components: rich procedural knowledge, rich factual knowledge, an understanding of different life contexts, an awareness of the relativism of values and priorities, and the ability to recognize and manage uncertainty.”
Psychology Today. (n.d.). Wisdom. Retrieved March 14, 2026.
No matter how you define wisdom, there is a need for staff with the gift of wisdom, which includes good judgment and the ability to see beyond the current context. Since generative AI provides users access to knowledge and organizes it for them, the days of just knowing enough seem numbered. In 2024, Chip Conley, writing for the Harvard Business Review, made the case for ‘wisdom workers,’ describing their role in organizations in relation to AI systems.
“Valuing human wisdom provides the ideal workplace balance to the rise of artificial intelligence. Although anybody who effectively distills life experiences can be wise, the more life lessons we’ve navigated, the more raw material for wisdom we possess. It’s time that we invest as much energy in helping older workers distill their wisdom as we do in helping younger workers accumulate their knowledge.”
Conley, C. (2024, August 2). Why “wisdom work” is the new “knowledge work”. Harvard Business Review. Boston.MA: Harvard Business Review Press.
Every day, we hear about cases where individuals have become so dependent on AI that it has gradually started to diminish their skills.
It is important to recognize that whilst wisdom is generally garnered from decades of life experiences, it is possible for a young adult, to display a wisdom well beyond their years.
If leadership is influence (see John Maxwell, Ch1), then sharing wisdom exemplifies leadership in action. When sharing wisdom helps the other person learn, it becomes educational—a process of shaping and guiding. It may be more effective to seek workers who can lead with wisdom and share it with others. Such wisdom-driven leaders and workers are often self-reflective, have a vibrant inner life, and excel at discernment. They record their lessons, often journaling regularly. Most importantly, they build connections with others and read widely. Mark C. Crowley, in his excellent book, ‘Lead From The Heart’ reminds us that wisdom doesn’t come only from the brain but also from the heart (see p28 of 235).
If wisdom is what we seek, then according to Socrates, wonder must be our starting point. To wonder means to be curious, to ask questions that are deep rather than superficial questions that seek the truth and may lead to awe. The use of ‘I-Wonder’ questions is fundamental to a pedagogy in schools that employs storytelling. These questions help to piece together the narrative that guides us toward the truth. Often, the questions revolve around: if, who, what, where, when, why.
Examples of ‘I-Wonder’ questions are:
- I wonder why we are doing it like this?
- I wonder if this organization could have a need for this?
- I wonder where and in which context this could be applied?
- I wonder how other approaches would work?
- I wonder when this might be achieved?
- I wonder who our wisdom people are?
The starting point is to ask questions that generate a variety of answers and additional questions. When done correctly, this not only uncovers the truth but also boosts curiosity and collaboration, increases ownership of the situation, and as a result, enhances employee engagement. It can also help build psychological safety, as Professor Amy C. Edmondson from Harvard Business School notes.
“Genuine questions convey respect for the other person – a vital aspect of psychological safety. Contrary to what many may believe, asking questions tends to make the leader seem not weak but thoughtful and wise.”
Edmondson, Amy C. (2019). The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth. Hoboken, New Jersey: John Wiley & Sons, Inc. (p. 186 of 286).
The garnering of information feeds the knowledge base of the organization and adds to the wisdom held by the ‘wisdom workers’. Socrates correctly deduced that “wonder is the beginning of wisdom.” In an ever changing world, it is the basis of all understanding.
“Mystery creates wonder and wonder is the basis of our desire to understand.”
Neil Armstrong
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