Leadership Wisdom and AI

By Hubert Saint-Onge

 1. Context

A small group of colleagues recently met to discuss an example of how AI can be applied to strategic planning.  It was only a few minutes into the meeting that one of the participants declared, “This is mind-blowing stuff.”  Even though all of us had toyed with AI in modest ways, the presenter with deep AI expertise outlined key strategic challenges facing a mid-size global business and the various ways they could be addressed based solely on information available on the web. He showed us how a robust AI framework could, in a day’s work, marshal information that would typically take months to prepare. 

After ‘kicking the tires’ for a while, we gained a new appreciation for what can be done with this technology. The discussion soon turned to the implications of this demo. The first realization was the productivity impact of this technology, given how quickly AI can compile information for a meaningful strategy discussion. Most organizations can only surmise the time required to carry out such an in-depth strategic review once a year. Secondly, our collective attention turned to the tremendous effects of this technology on how organizations function. The AI expert pointed out that this technology is not only rapidly penetrating organizations but is also increasing its capabilities at an ever-accelerating pace.  

Our gaze shifted to the changing role of leaders as this technology not only gathers information but also synthesizes, analyzes it, and employs powerful reasoning to arrive at conclusions and choices. The realization then comes to mind that the wisdom leaders bring becomes their key contribution in this new organizational context. The new kind of leadership required is not only smart and responsible but also brings the wisdom that technology alone cannot provide. This is the focus of this article: how do we recognize wisdom in a leader, how do leaders develop wisdom, and how do we modify the role of the wise leaders to enhance their impact in a context where they must embrace and cultivate the collaboration between human and artificial intelligence.

2.     How do we recognize wisdom in leaders? 

Stay calm under pressure. The wisdom a leader has acquired is most visibly demonstrated through their consistent behaviours and practices, especially under pressure. A cornerstone of this is strong emotional regulation; wise leaders possess the ability to remain calm, composed, and thoughtful even amid crises or significant stress, understanding that their emotional state has a ripple effect on their teams.

Inquire before taking action. They are adept at asking better questions rather than rushing to provide answers or impose solutions, using inquiry to uncover the root causes of issues, stimulate critical thinking in others, and ensure a comprehensive understanding before making decisions.

Express thoughts clearly and succinctly. Their communication is often characterized by the principle of speaking less but ensuring their words carry more weight and meaning, prioritizing clarity, impact, and conciseness over sheer volume. They often refer to “principles” they have arrived at through experience, continually testing and refining the principles that guide them. They draw on these principles when providing guidance to others.

Take their ego out of the equation and focus on how others are impacted. A defining trait is their commitment to choosing progress over ego; they can set aside personal ambition or the need to be "right" in favour of what is best for the team, the organization, or the broader mission. This is often linked to a well-developed sense of patience and a long-term perspective, allowing them to understand that meaningful achievements and sustainable change unfold over time. They avoid the pitfalls of short-term expediency.

Engender trust around them. Fundamentally, wise leadership is built on a bedrock of integrity and trust. They consistently act in alignment with their values, demonstrate fairness and transparency in their dealings, and foster an environment where people feel safe, respected, and empowered, knowing that their leader is reliable and principled. These intertwined characteristics are not just admirable personal qualities but are the active manifestations of a leader who has diligently cultivated wisdom.

3.     How is a wise leader different from a smart leader?

Smart leaders quickly impose their solutions to complex problems, while wise leaders are more reflective. Smart leaders are more self-contained, rapidly forming their own opinions on how to resolve challenges and pressing to apply their solutions. They tend to be hyperactive, quickly moving from one thing to the next. People who have worked for smart leaders for some time know the pattern and wait for their leader to tell them what to do. When it fails, they consult others to forge collectively defined solutions. Wise leaders think things through by connecting the dots between everything they’ve seen, done, and learned to give shape to their judgment and perspective. They embody the principle of going slower to go faster. Although there are notable exceptions, becoming wise requires experience. They know which issues are worth the effort, which situations to avoid, and what to say to keep everyone committed to implementing the right solutions.

It is judgment that most discerns whether a leader is smart or wise. The smart leader thinks logically and applies their logic within their decision-making process to produce the best outcome. Wise leaders go beyond this to leverage the intuition, judgment and principles they have developed over time. Experience informs their judgment and shapes how they approach a problem. Wise leaders apply a wide range of knowledge, personal experience, and acquired insights to inform their judgment.

Facts versus Synthesis. The overuse of intelligence can lead a leader to hyper-focus on individual facts or data points that are immediately apparent, instead of the patterns or trends that comprise the bigger picture emerging from the data. The ability to see patterns flows from tapping into the wisdom of experience, which enables you to see not just the dots but to connect them. Wise leaders give themselves the space to see the patterns.

A wise leader can give simple answers to complex questions. Smart leaders depend on their intelligence, logic, and data to reason things out, believing that this will lead them to the best outcomes. Wise leaders do what AI cannot do: they believe sound judgment is more important than the power to reason with facts and data. In a way, smart leaders work on the same playing field as AI, synthesizing data and, while leaders with wisdom supersede them. Intelligence is usually about generating or acquiring knowledge, while wisdom is about exercising sound judgment in applying that knowledge. The brains of wise leaders are connecting the dots between everything they’ve seen, done, and learned to offer judgment and perspective.

How does a leader evolve to strike a productive balance between being a smart and a wise leader?  While the quick-minded leader tends to move at a fast pace, the wise leader values informed decision-making, ensures that decisions are well thought through, and considers the long-term consequences for all stakeholders involved. There are other simple distinctions between intelligence and wisdom that you can use as a guide to determine in which direction you lean or, better yet, what it looks like to strike a productive balance between the two. The smart leader can over-index on a transactional approach by driving results quickly and under-index on the relationships that make long-term results possible.  Wise leaders take the time to nurture relationships. Their engagement with people in a more inspiring manner builds trust and alignment, which makes it possible to overcome challenges collaboratively. Why would it not be possible for someone to strive for an optimal balance between these two distinctive propensities?

4.     How do leaders acquire wisdom?

Learning from experience.  Experience is the primary source of wisdom, particularly as it relates to situations that test leaders’ mettle and push them beyond their comfort zone.Navigating complex challenges, making high-stakes decisions with imperfect information, and grappling with their results give shape to the most meaningful lessons.

Reaching agreement on difficult issues. Working through a controversial topic requires listening to all points of view with empathy and a genuine interest in the perspectives of others, even when contradicting their own. The more leaders consider how their actions and choices will impact those around them, the more their judgments incorporate the subtle context critical for sound decision making. Thinking through the intended and unintended consequences regarding everything they do is how smart leaders become wise.

Learning from Failures. The development of wisdom is not based on the number of experiences but rather depends on the learnings derived from these experiences, especially failures and missteps.  Instead of viewing errors as purely negative events to be buried or forgotten, wise leaders treat them as invaluable data points for growth. They engage in a rigorous process of dissecting what went wrong, understanding the contributing factors and resolving to adapt their own approaches and behaviours accordingly. Such learning ensures that mistakes are not repeated but instead become stepping stones, contributing to a deeper understanding of themselves, their teams, and the complexities of their operating environment. The lessons gleaned from their mistakes ultimately serve a broader, positive purpose and contribute to improving their organization. While experience provides the raw material, it is through dedicated reflection and honest self-evaluation that this material is refined into wisdom.

Purposefully look for insights. Taking deliberate reflective pauses allows leaders to step back from the immediate pressures of daily tasks and process their experiences more deeply, connect disparate pieces of information, engage in creative problem-solving, and develop coherent long-term strategies. It is in these moments of quiet contemplation that insights can surface, and the underlying patterns and principles behind successes and failures can be discerned. Self-knowing involves a courageous and ongoing examination of one's own beliefs, values, emotional triggers, strengths, and, importantly, weaknesses. It's about understanding how these internal factors shape their perceptions and actions. Cultivating this level of self-awareness requires genuine humility.

Seeking Counsel.  Wisdom is an emergent quality nurtured by a willingness to seek out and integrate the insights of others. Mentorship can play a critical role in this process, offering leaders the opportunity to learn from individuals who have navigated similar paths and accumulated a wealth of experience. Engaging in active, deep listening, leaders can absorb invaluable lessons and gain wisdom that might otherwise take years to acquire firsthand. By asking thoughtful, profound questions and delving into a mentor's decision-making processes, their most significant learnings, or the books and experiences that shaped them.

Challenging one’s own assumptions is an inherent part of developing wisdom. All of us have assumptions and mindsets, but they are so intrinsically integrated into how we think and react that we often struggle to recognize them. The best way to understand how they shape our thinking and reactions is to engage with people who have different points of view. This means intentionally seeking out input from individuals with various backgrounds, experiences, thinking styles, and expertise. This approach is especially important when making critical decisions or facing unfamiliar challenges: it helps uncover blind spots and ultimately leads to more robust, well-rounded, and effective decision-making. Over time, this approach cultivates environments where different viewpoints are not only tolerated but actively solicited and valued, ultimately leading to the recognition that a monolithic understanding rarely solves complex problems.

5.     How can leaders assess their ability to exercise wisdom?

Given the more ethereal nature of wisdom, assessing one’s ability to exercise wisdom is a nuanced and ongoing process that requires deep introspection, a willingness to be self-critical, and a commitment to continuous self-improvement. It involves engaging in honest self-appraisal across various facets of leadership behaviours and decision-making. Leaders can employ several ways to gauge their capacity for wisdom.  

Structured reflection on the impact of past decisions. Assessing one's own ability to exercise wisdom is a nuanced and ongoing process that requires deep introspection, a willingness to seek uncomfortable truths, and a commitment to continuous self-improvement. It's not about ticking boxes on a checklist, but instead engaging in honest self-appraisal across various facets of leadership behaviour and decision-making. Leaders can employ several methods to gain insight into their capacity for wisdom.

Structured Reflection on Past Decisions and Their Impacts. A primary method for self-assessment involves a rigorous and honest review of significant past decisions, particularly those that were complex, had far-reaching consequences, or produced unexpected outcomes. Leaders can ask themselves questions such as:

• Did I genuinely consider all relevant perspectives, especially dissenting ones, or did I succumb to confirmation bias?

• What were the short-term versus long-term consequences of my decision, and did I adequately weigh them?

• To what extent did my assumptions, ego, or emotional state influence my judgment at the time?

• What were the ethical implications, and were they given due consideration?

• What did I learn from the process and the outcome, and how has that learning been integrated into my subsequent actions?

Analyzing these past events with a "wisdom lens" can reveal patterns in decision-making that indicate areas of strength or consistent blind spots where wisdom may be lacking. This isn't about self-criticism for its own sake but about extracting valuable lessons.

Actively soliciting and scrutinizing diverse feedback. While self-reflection is an internal process, wisdom is often perceived and experienced by others. Therefore, actively seeking comprehensive, candid feedback from a diverse range of individuals—superiors, peers, direct reports, mentors, and even external stakeholders—is vital for assessing one's wisdom. This may involve specifically asking for input on aspects such as fairness in decision-making, the ability to listen and understand different viewpoints, composure and clarity under pressure, the inclusivity of one's leadership style, and the perceived long-term vision. Leaders must then critically analyze this feedback, looking for recurring themes and being particularly attentive to comments that challenge their self-perception. The self-assessment component lies in the leader's ability to process this feedback without defensiveness, identify actionable insights, and gauge the alignment (or misalignment) between their intended wisdom and how it is manifested and perceived by those they influence.  

Journaling for insight into decision-making patterns. Regular, reflective journaling can serve as a powerful tool for self-assessing wisdom. By consistently documenting challenging situations, the decision-making process employed, the emotional responses experienced, and the lessons learned, leaders can uncover subtle patterns and default tendencies in their thinking and behaviour over time. For instance, a journal might reveal a tendency to react impulsively under stress rather than pausing to reflect, or a pattern of avoiding difficult conversations that could lead to wiser, albeit more challenging, solutions. It can also highlight moments where the leader successfully navigated complexity with foresight and empathy. This practice provides a private space for honest self-appraisal and can illuminate how well a leader is managing their emotions, considering ethical dimensions, and learning from daily experiences—all critical components of exercising wisdom.

Evaluating long-term outcomes through a "wisdom lens". Leaders can assess their wisdom by scrutinizing the broader and longer-term impacts of their leadership and decisions, moving beyond immediate, easily quantifiable metrics like profit margins or project completion rates. This involves asking:

• Are my actions fostering a culture of trust, psychological safety, and ethical behaviour?

• Are we achieving sustainable success that benefits multiple stakeholders, or are short-term gains creating long-term problems?

• Are people growing and developing under my leadership?

• Is there a sense of shared purpose and well-being within the team or organization?

A wise leader creates positive ripples that extend beyond the balance sheet. By evaluating outcomes holistically, considering the human and systemic effects of their influence, leaders can gain a deeper understanding of whether their actions are truly wise and constructive in the fullest sense. 

Conducting a "pre-mortem" exercise on forthcoming events. This exercise  enables a proactive self-assessment by engaging in a mental exercise that tests judgment against wisdom principles. For instance, when facing a significant upcoming decision, a leader can conduct a "pre-mortem," imagining potential ways the decision could go wrong and then considering how a wise approach would anticipate and mitigate these risks or adapt to unforeseen challenges. They can also pose hypothetical complex ethical dilemmas to themselves and analyze how they would respond, paying close attention to the values they would prioritize and the reasoning they would employ. This kind of scenario analysis allows leaders to "practice" wisdom and identify areas where their current thinking might be reactive, overly simplistic, or lacking in foresight before real-world consequences are at stake.

Monitoring Humility, Openness to Learning, and Adaptability. A key indicator of wisdom is intellectual humility and a genuine commitment to learning. Leaders can assess themselves by asking:

• How frequently do I actively seek out dissenting opinions or perspectives that differ from my own?

• How do I react when my strongly held beliefs are challenged with credible evidence?

• Am I willing to admit when I am wrong or when I don't know the answer?

• Do I actively engage in learning activities that stretch my understanding and push me out of my comfort zone?

A leader who consistently demonstrates openness, a willingness to adapt their views in the face of new information, and the humility to acknowledge their fallibility is likely cultivating and exercising wisdom. Conversely, a pattern of defensiveness, dogmatism, or a reluctance to learn signals a barrier to wisdom. By consistently applying these self-assessment methods, leaders can gain a more accurate picture of their capacity for wisdom, identify areas for development, and consciously cultivate the qualities that enable them to lead with greater insight, prudence, and positive impact.

6.     The complementary interplay between a wise leader and AI

What we have covered in this paper so far enables us to examine in more depth how to build complementarity between the emerging capabilities of artificial intelligence and the enduring importance of wisdom in leadership. As AI systems become more adept at collecting, analyzing, and even generating insights from vast datasets, and as they begin to articulate complex rationales for potential actions, the unique contribution of human wisdom in leadership becomes even more critical. Wisdom, in this context, transcends mere data processing and logical deduction; it encompasses a deep understanding of human nature, ethical considerations, contextual nuances, and the long-term consequences of decisions. While AI can provide leaders with powerful analytical tools and potential pathways forward, it lacks the nuanced judgment and holistic perspective that wisdom cultivates.  

One crucial role of wisdom in leadership is its ability to discern not just what can be done, but what should be done. AI operates based on algorithms and the data it is trained on, which, while powerful, may not always align with fundamental human values, ethical principles, organizational trust and integrity, or the broader societal good. Wisdom, honed through experience, reflection, and empathy, allows leaders to navigate complex ethical dilemmas, weigh competing values, and make decisions that are not only efficient but also just and morally sound. It involves understanding the potential impact of actions on organizational stakeholders, communities, and future generations in a way that purely data-driven approaches may overlook. The underlying questions on the role of leadership wisdom in complementing AI go beyond the role of an ethical compass to ensure that the power of AI is harnessed responsibly and in service of meaningful organizational goals.  

Wisdom provides leaders with the judgment, intuition and overall crucial ability to navigate the inherent uncertainties and ambiguities of the real world. While AI excels at identifying patterns and probabilities based on past data, it often struggles with emerging situations, unforeseen consequences, and the unpredictable nature of human behaviour. Wise leaders, drawing on their accumulated experience and intuitive understanding, can make sound judgments even when faced with incomplete information or conflicting signals. They possess a form of "practical intelligence" that allows them to adapt strategies, build resilience, and inspire trust in the face of uncertainty. This ability to navigate the unknown with prudence and foresight remains a uniquely human attribute that complements the analytical power of AI.  

Finally, wisdom in leadership fosters a deeper connection with and understanding of the human element within an organization and its broader ecosystem. It involves recognizing the importance of relationships, empathy, and effective communication in achieving collective goals. While AI can analyze sentiment and identify communication patterns, it cannot replicate the genuine human connection that a wise leader cultivates through active listening, emotional intelligence, and a genuine concern for the well-being of others. This human-centred approach, grounded in wisdom, builds stronger teams, fosters a more positive and productive work environment, and ultimately leads to more sustainable and impactful outcomes than purely transactional or data-driven leadership styles. In essence, as AI takes on more of the analytical and rational aspects of decision-making, the role of wisdom in providing ethical guidance, navigating uncertainty, and fostering meaningful human connections becomes essential for effective and responsible decision-making.

Here are concrete steps to build complementarity between leadership wisdom and AI:

Firstly, we must build bridges that integrate human wisdom with the increasing capabilities of AI to enable effective collaborations between people and AI systems. It’s unlikely that the thorny problems and dilemmas of business can be solved by algorithms alone. To help leaders leverage their wisdom to the fullest, we must consider a multifaceted approach that focuses on creating the right environment, fostering specific skills, and implementing bridging processes.

Secondly, we need to equip wise leaders with the skills necessary to interact with and interpret the outputs of AI systems effectively. This doesn't mean they need to become AI experts, but rather develop a strong understanding of the capabilities and limitations of these technologies. They should be able to ask insightful questions of AI, critically evaluate its suggestions, and understand the biases and shortcomings that might be embedded in the data it uses. This requires fostering a degree of digital literacy and critical evaluation skills among leaders, enabling them to see AI as a powerful tool rather than a replacement for human judgment. They need to be able to translate the data-driven insights of AI into a broader human context, informed by their wisdom.

Thirdly, we must foster genuine collaboration between wise leaders and AI systems. This involves designing workflows and processes that allow for a synergistic partnership. AI can handle the heavy lifting of data analysis and pattern recognition, freeing up leaders to focus on the more nuanced aspects of decision-making that require wisdom, such as ethical considerations, stakeholder impact, and long-term vision.  This collaboration requires disciplined questioning and mutual respect between the human leader and the AI system, with each recognizing the unique strengths the other brings to the table.  Leaders must act as the curators and interpreters of AI insights, applying their wisdom to contextualize and refine the recommendations.

With these measures in place, the bridges they provide will ensure complementarity between leadership wisdom and AI in organizations.  

7.     Conclusion

The development of wisdom is a long, continuous process for all leaders. They need to pursue learning and development opportunities to enhance their critical thinking, ethical reasoning, emotional intelligence, and systems thinking. Exposure to diverse experiences, perspectives, and challenging situations can further hone their wisdom. To enrich their capacity for wise leadership in an increasingly complex world shaped by AI, they must be thoughtful in pursuing their development and that of others around them. Leadership wisdom will be at an even greater premium as AI becomes increasingly pervasive:  wise leaders not only must navigate the age of AI effectively but also leverage their unique human wisdom to build a more prosperous and ethical future.